US 7,459,414 B2
Herbicides
Thomas Maetzke, Münchenstein (Switzerland); André Stoller, Blotzheim (France); Sebastian Wendeborn, Binningen (Switzerland); and Henry Szczepanski, Wallbach (Switzerland)
Assigned to Syngenta Crop Protection, Inc., Greensboro, N.C. (US)
Filed on Mar. 18, 2005, as Appl. No. 11/83,465.
Application 11/083465 is a division of application No. 10/070767, filed on Jun. 25, 2002, granted, now 6,894,005.
Prior Publication US 2005/0187110 A1, Aug. 25, 2005
Int. Cl. A01N 31/06 (2006.01); C07C 49/537 (2006.01)
U.S. Cl. 504—218  [504/221; 504/223; 504/235; 504/238; 504/254; 504/269; 504/348; 540/562; 540/567; 544/3; 544/63; 544/230; 544/234; 544/235; 544/240; 544/349; 546/296; 548/366.4; 548/367.1; 548/408; 548/410; 548/544; 568/330] 5 Claims
 
1. A selective-herbicidal composition comprising a mixture of
a) a herbicidally effective amount of a compound of formula I

OG Complex Work Unit Drawing
wherein
R1 and R3 are each independently of the other ethyl, haloethyl, ethynyl, C1-C2alkoxy, C1-C2haloalkoxy, C1-C2alkylcarbonyl, C1-C2hydroxyalkyl or C1-C2alkoxycarbonyl;
Q is a group

OG Complex Work Unit Drawing

OG Complex Work Unit Drawing
R4 and R5 are each independently of the other C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C2-C10—N-alkoxyiminoalkyl, C2-C10alkoxycarbonylalkyl, C1-C10aminoalkyl, C3-C10dialkylaminoalkyl, C2-C10alkylaminoalkyl, C1-C10cyanoalkyl, C4-C10cycloalkylalkyl, C1-C10phenylalkyl, C1-C10heteroarylalkyl, C1-C10phenoxyalkyl, C1-C10heteroaryloxyalkyl, C1-C10alkylideneaminooxyalkyl, C1-C10nitroalkyl, C1-C10trialkylsilylalkyl, C2-C10alkylaminocarbonylalkyl, C2-C10dialkylaminocarbonylalkyl, C2-C10alkylaminocarbonyloxyalkyl, C3-C10dialkylaminocarbonyloxalkyl, C2-C10alkoxycarbonylaminoalkyl, C1-C10—N-alkoxycarbonyl-N-alkylaminoalkyl, C1-C10cycloalkyl, aryl or heteroaryl; or
R4 and R5, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur and that, in addition, may contain a fused or spiro-bound alkylene or alkenylene chain consisting of from 2 to 6 carbon atoms, which chain may in turn contain one or two hetero atoms selected from oxygen and sulfur, wherein the cyclic group may be substituted by phenyl or benzyl, which in turn may be substituted by halogen, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, hydroxy, C1-C6alkoxy C1-C6alkoxy-C1-C6alkoxy, C1-C6haloalkoxy or by nitro;
R2, R6 and R32 are each independently of the others C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R7, R31 and R33 are each independently of the others hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C2-C10alkoxyalkyl;
R8 is hydrogen, C1-C10alkyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10-alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
R6 and R7 or R2 and R31 or R32 and R33, together with the atom to which they are bonded, form a saturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur; or R6 and R8, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R9, R10, R11 and R12 are each independently of the others C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
R9 and R11 or R9 and R10, together with the atoms to which they are bonded, form a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R13, R14, R34 and R35 are each independently of the others C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
R13 and R14 or R34 and R35, together with the atoms to which they are bonded, from a 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R15 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C2-C10alkoxycarbonylalkyl, C1-C10aminoalkyl, C3-C10dialkylaminoalkyl, C2-C10alkylaminoalkyl, C1-C10cyanoalkyl, C4-C10cycloalkylalkyl, C1-C10phenylalkyl, C1-C10heteroarylalkyl, C1-C10phenoxyalkyl, C1-C10heteroaryloxyalkyl, C1-C10nitroalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R16 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthiolkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R17 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R18 is hydrogen, C2-C10alkenyl, C2-C10alkynyl, C1-C10alkyl or C1-C10alkoxyalkyl; or
R17 and R18, together with the atoms to which they are bonded, form a 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
Y is oxygen, sulfur, C—R19 or N—R36;
R19 and R36 are each independently of the other C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, phenyl or heteroaryl; or
R18 and R19 or R18 and R36, together with the atom to which they are bonded, form a saturated 5- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
G1, G2, G3, G4, G5, G6, G7, G8, G9 and G10 are each independently of the others hydrogen, —C(X1)—R20, —C(X2)—X3—R21, —C(X4)—N(R22)—R23, —SO2—R24, an alkali metal cation, alkaline earth metal cation, sulfonium cation or ammonium cation, —P(X5)(R25)—R26 or —CH2—X6—R27;
X1, X2, X3, X4, X5 and X6 are each independently of the others oxygen or sulfur;
R20, R21, R22 and R23 are each independently of the others hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl, C1-C5alkyl, C2-C10alkoxyalkyl, C4-C10alkenyloxyalkyl, C4-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C1-C5alkylsulfoxyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylideneaminooxy-C1-C5alkyl, C1-C5alkylcarbonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminocarbonyl-C1-C5alkyl, C1-C5alkylcarbonylamino-C1-C5alkyl, C1-C5alkylcarbonyl-(C2-C5alkyl)-aminoalkyl, C3-C6trialkylsilyl-C1-C5alkyl, phenyl-C1-C5alkyl, heteroaryl-C1-C5alkyl, phenoxy-C1-C5alkyl, heteroaryloxy-C1-C5alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or heteroaryl or heteroarylamino, or heteroaryl or heteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diheteroarylamino, or diheteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, phenylamino, or phenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diphenylamino, or diphenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or C3-C7cycloalkylamino, di-C3-C7cycloalkylamino or C3-C7cycloalkoxy;
R24, R25 and R26 are hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl, C4-C10alkenyloxyalkyl, C4-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C1-C5alkylsulfoxyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylideneaminooxy-C1-C5alkyl, C1-C5alkylcarbonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminocarbonyl-C1-C5alkyl, C1-C5alkylcarbonylamino-C1-C5alkyl, C1-C5alkylcarbonyl-(C2-C5alkyl)-aminoalkyl, C3-C6trialkylsilyl-C1-C5alkyl, phenyl-C1-C5alkyl, heteroaryl-C1-C5alkyl, phenoxy-C1-C5alkyl, heteroaryloxy-C1-C5alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or heteroaryl or heteroarylamino, or heteroaryl or heteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diheteroarylamino, or diheteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3haloalkoxy, halogen, cyano or by nitro, phenylamino, or phenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diphenylamino, or diphenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or C3-C7cycloalkylamino, di-C3-C7cycloalkylamino, C3-C7cycloalkoxy, C1-C10alkoxy, C1-C10haloalkoxy, C1-C5alkylamino, C2-C8dialkylamino, benzyloxy or phenoxy, wherein the benzyl and phenyl groups may in turn be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
R27 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl, C4-C10alkenyloxyalkyl, C4-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C1-C5alkylsulfoxyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylideneaminooxy-C1-C5alkyl, C1-C5alkylcarbonyl-C1-C5-alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminocarbonyl-C1-C5alkyl, C1-C5alkylcarbonylamino-C1-C5alkyl, C1-C5alkylcarbonyl-(C2-C5alkyl)-aminoalkyl, C3-C6trialkylsilyl-C1-C5alkyl, phenyl-C1-C5alkyl, heteroaryl-C1-C5alkyl, phenoxy-C1-C5alkyl, heteroaryloxy-C1-C5alkyl, C2-C5alkenyl, C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl, or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or heteroaryl or heteroarylamino, or heteroaryl or heteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, diheteroarylamino, diheteroarylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, or phenylamino, phenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, halogen, cyano or by nitro, diphenylamino, diphenylamino substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, C3-C7cycloalkylamino, di-C3-C7cycloalkylamino, C3-C7cycloalkoxy or C1-C10alkylcarbonyl;
Y2 is oxygen, sulfur, C—R140—R141 or N—R142,
R55 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C2-C10alkylcarbonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl;
R137 is hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C1-C10alkoxyalkyl; or
R55 and R137, together with the atoms to which they are bonded, form a 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R138 and R139 are each independently of the other hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C2-C10alkoxyalkyl; and
R140 and R141 are each independently of the other hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl or C1-C10alkoxyalkyl; or
R55 and C—R140, together with the atoms to which they are bonded, form a saturated or unsaturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
R142 is hydrogen, C1-C10alkyl, C1-C10haloalkyl, C2-C10alkoxyalkyl, C3-C10alkenyloxyalkyl, C3-C10alkynyloxyalkyl, C2-C10alkylthioalkyl, C2-C10alkylsulfinylalkyl, C2-C10alkylsulfonylalkyl, C3-C10cycloalkyl, aryl or heteroaryl; or
R55 and N—R142, together with the atoms to which they are bonded, form a saturated or unsaturated 3- to 7-membered cyclic group that may contain one or two hetero atoms selected from nitrogen, oxygen and sulfur;
or an agronomically tolerable salt, isomer or enantiomer of such a compound; and
b) a herbicide-antagonistically effective amount either of a compound of formula X

OG Complex Work Unit Drawing
wherein
R37 is hydrogen, C1-C8alkyl, or C1-8alkyl substituted by C1-C6alkoxy or by C3-C6alkenyloxy; and X7 is hydrogen or chlorine; or of a compound of formula XI

OG Complex Work Unit Drawing
wherein
E is nitrogen or methine;
R38 is —CCl3, phenyl or phenyl substituted by halogen;
R39 and R40 are each independently of the other hydrogen or halogen; and
R41 is C1-C4alkyl; or of a compound of formula XII

OG Complex Work Unit Drawing
wherein R44 and R45 are each independently of the other hydrogen or halogen, and
R46, R47 and R48 are each independently of the others C1-C4alkyl, or of a compound of formula XIII

OG Complex Work Unit Drawing
R51 and R52 are each independently of the other hydrogen, C1-C8alkyl, C3-C8cycloalkyl, C3-C6alkenyl, C3-C6alkynyl,

OG Complex Work Unit Drawing
or C1-C4alkyl substituted by C1-C4alkoxy or by

OG Complex Work Unit Drawing
or R51 and R52 together form a C4-C6alkylene bridge that may be interrupted by oxygen, sulfur, SO, SO2, NH or by —N(C1-C4alkyl)-;
R53 is hydrogen or C1-C4alkyl;
R49 is hydrogen, halogen, cyano, trifluoromethyl, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj, —CONRkRm, —CORn, —SO2NRkRm or —OSO2—C1-C4alkyl;
R9 is hydrogen, halogen, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj, —CONRkRm, —CORn, —SO2NRkRm, —OSO2—C1-C4alkyl, C1-C6alkoxy, or C1-C6alkoxy substituted by C1-C4alkoxy or by halogen, C3-C6alkenyloxy, or C3-C6alkenyloxy substituted by halogen, or C3-C6alkynyloxy, or R49 and R50 together form a C3-C4alkylene bridge that may be substituted by halogen or by C1-C4alkyl, or together form a C3-C4alkenylene bridge that may be substituted by halogen or by C1-C4alkyl, or together form a C4alkadienylene bridge that may be substituted by halogen or by C1-C4alkyl;
R50 and Rh are each independently of the other hydrogen, halogen, C1-C4alkyl, trifluoromethyl, C1-C6alkoxy, C1-C6alkylthio or —COORj;
Rc is hydrogen, halogen, nitro, C1-C4alkyl or methoxy; Rd is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm;
Re is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy, or Rd and Re together form a C3-C4alkylene bridge;
Rp is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy; Rq is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm; or Rp and Rq together form a C3-C4alkylene bridge;
Rr is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy; Rs is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm; or Rr and Rs together form a C3-C4alkylene bridge;
Rt is hydrogen, halogen, C1-C4alkyl, —COORj, trifluoromethyl or methoxy; Ru is hydrogen, halogen, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, —COORj or CONRkRm; or Rv and Ru together form a C3-C4alkylene bridge;
Rf and Rv are hydrogen, halogen or C1-C4alkyl;
Rx and Ry are each independently of the other hydrogen, halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, —COOR54, trifluoromethyl, nitro or cyano;
Rj, Rk and Rm are each independently of the others hydrogen or C1-C4alkyl; or
Rk and Rm together form a C4-C6alkylene bridge that may be interrupted by oxygen, NH or by —N(C1-C4alkyl)-;
Rn is C1-C4alkyl, phenyl, or phenyl substituted by halogen, C1-C4alkyl, methoxy, nitro or by trifluoromethyl;
R54 is hydrogen, C1-C10alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylthio-C1-C4alkyl, di-C1-C4alkylamino-C1-C4alkyl, halo-C1-C8alkyl, C2-C8alkenyl, halo-C2-C8alkenyl, C3-C8alkynyl, C3-C7cycloalkyl, halo-C3-C7cycloalkyl, C1-C8alkylcarbonyl, allylcarbonyl, C3-C7cycloalkylcarbonyl, benzoyl, which is unsubstituted or substituted on the phenyl ring identically or differently up to three times by halogen, C1-C4alkyl, halo-C1-C4alkyl, halo-C1-C4alkoxy or C1-C4alkoxy; or furoyl, thienyl; or C1-C4alkyl substituted by phenyl, halophenyl, C1-C4alkylphenyl, C1-C4alkoxyphenyl, halo-C1-C4alkylphenyl, halo-C1-C4alkoxyphenyl, C1-C6alkoxycarbonyl, C1-C4alkoxy-C1-C8alkoxycarbonyl, C3-C8alkenyloxycarbonyl, C3-C8alkynyloxycarbonyl, C1-C8alkylthiocarbonyl, C3-C8alkenylthiocarbonyl, C3-C8alkynylthiocarbonyl, carbamoyl, mono-C1-C4alkylaminocarbonyl, di-C1-C4alkylaminocarbonyl; or phenylaminocarbonyl, which is unsubstituted or substituted on the phenyl identically or differently up to three times by halogen, C1-C4alkyl, halo-C1-C4alkyl, halo-C1-C4alkoxy or C1-C4alkoxy or once by cyano or nitro; or dioxolan-2-yl, which is unsubstituted or substituted by one or two C1-C4alkyl radicals, or dioxan-2-yl, which is unsubstituted or substituted by one or two C1-C4alkyl radicals, or C1-C4alkyl, which is substituted by cyano, nitro, carboxyl or by C1-C8alkylthio-C1-C8alkoxycarbonyl;
or of a compound of formula XIV

OG Complex Work Unit Drawing
wherein R56 and R57 are each independently of the other C1-C6alkyl or C2-C6alkenyl; or R56 and R57 together are

OG Complex Work Unit Drawing
R58 and R59 are each independently of the other hydrogen or C1-C6alkyl; or R56 and R57 together are

OG Complex Work Unit Drawing
R60 and R61 are each independently of the other C1-C4alkyl, or R60 and R61 together are —(CH2)5—;
R62 is hydrogen, C1-C4alkyl or

OG Complex Work Unit Drawing
or R56 and R57 together are

OG Complex Work Unit Drawing
R63, R64, R65, R66, R67, R68, R69, R70, R71, R72, R73, R74, R75, R76, R77 and R78 are each independently of the others hydrogen or C1-C4alkyl;
or of a compound of formula XV

OG Complex Work Unit Drawing
wherein R80 is hydrogen or chlorine and R79 is cyano or trifluoromethyl;
or of a compound of formula XVI

OG Complex Work Unit Drawing
wherein R81 is hydrogen or methyl;
or of a compound of formula XVI

OG Complex Work Unit Drawing
wherein R81 is hydrogen or methyl;
or of a compound of formula XVII

OG Complex Work Unit Drawing
wherein
R82 is hydrogen, C1-C4alkyl, or C1-C4alkyl substituted by C1-C4alkyl-X2— or by C1-C4haloalkyl-X2—, or is C1-C4haloalkyl, nitro, cyano, —COOR85, —NR86R87, —SO2NR88R89 or —CONR90R91;
R83 is hydrogen, halogen, C1-C4alkyl, trifluoromethyl, C1-C4alkoxy or C1-C4haloalkoxy;
R84 is hydrogen, halogen or C1-C4alkyl;
U, V, W1 and Z4 are each independently of the others oxygen, sulfur, C(R92)R93, carbonyl, NR94, or a group

OG Complex Work Unit Drawing
wherein R102 is C2-C4alkenyl or C2-C4alkynyl; with the provisos that
a) at least one of the ring members U, V, W1 or Z4 is carbonyl, and a ring member adjacent to that ring member or to those ring members is the group

OG Complex Work Unit Drawing
that group appearing only once; and
b) two adjacent ring members U and V, V and W1 and W1 and Z4 cannot simultaneously be oxygen;
R95 and R96 are each independently of the other hydrogen or C1-C8alkyl; or
R95 and R96 together form a C2-C6alkylene group;
A1 is R99—Y1— or —NR97R98;
X2 is oxygen or —S(O)s;
Y1 is oxygen or sulfur;
R99 is hydrogen, C1-C8alkyl, C1-C8haloalkyl, C1-C4alkoxy-C1-C8alkyl, C3-C6alkenyloxy-C1-C8alkyl, or phenyl-C1-C8alkyl in which the phenyl ring may be substituted by halogen, C1-C4alkyl, trifluoromethyl, methoxy or by methyl-S(O)s—, or is C3-C6alkenyl, C3-C6haloalkenyl, phenyl-C3-C6-alkenyl, C3-C6alkynyl, phenyl-C3-C6alkynyl, oxetanyl, furyl or tetrahydrofuryl;
R85 is hydrogen or C1-C4alkyl;
R86 is hydrogen, C1-C4alkyl or C1-C4alkylcarbonyl;
R87 is hydrogen or C1-C4alkyl; or
R86 and R87 together form a C4- or C5-alkylene group;
R88, R89, R90 and R91 are each independently of the others hydrogen or C1-C4alkyl; or R88 together with R89, or R90 together with R91, are each independently of the other C4- or C5-alkylene in which one carbon atom may have been replaced by oxygen or by sulfur, or one or two carbon atoms may have been replaced by —NR100—;
R92, R100 and R93 are each independently of the others hydrogen or C1-C8alkyl; or
R92 and R93 together are C2-C6alkylene;
R94 is hydrogen or C1-C8alkyl;
R97 is hydrogen, C1-C8alkyl, phenyl or phenyl-C1-C8alkyl, wherein the phenyl rings may be substituted by fluorine, chlorine, bromine, nitro, cyano, —OCH3, C1-C4alkyl or by CH3SO2—, or is C1-C4alkoxy-C1-C8alkyl, C3-C6alkenyl or C3-C6alkynyl;
R98 is hydrogen, C1-C8alkyl, C3-C6alkenyl or C3-C6alkynyl; or
R97 and R98 together are C4- or C5-alkylene in which one carbon atom may have been replaced by oxygen or by sulfur, or one or two carbon atoms may have been replaced by —NR101—;
R101 is hydrogen or C1-C4alkyl;
r is 0 or 1; and
s is 0, 1 or 2,
or of a compound of formula XVIII

OG Complex Work Unit Drawing
wherein R103 is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl or C3-C6alkynyl; and R104, R105 and R106 are each independently of the others hydrogen, C1-C6alkyl, C3-C6cycloalkyl or C1-C6alkoxy, with the proviso that one of the substituents R104, R105 and R106 is other than hydrogen;
or of a compound of formula XIX

OG Complex Work Unit Drawing
wherein Z5 is N or CH, n is 0, 1, 2 or 3 when Z5 is N, and n is 0, 1, 2, 3 or 4 when Z5 is CH, R107 is halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, nitro, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkoxycarbonyl, phenyl or phenoxy, or phenyl or phenoxy substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
R108 is hydrogen or C1-C4alkyl, R109 is hydrogen, C1-C4alkyl, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C1-C4alkylthio-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-4alkenyloxy-C1-C4alkyl or C1-C4-alkynyloxy-C1-C4alkyl;
or of a compound of formula XX

OG Complex Work Unit Drawing
wherein Z6 is oxygen or N—R110 and R110 is a group of formula

OG Complex Work Unit Drawing
wherein R111 and R112 are each independently of the other cyano, hydrogen, C1-C4alkyl, C3-C6-cycloalkyl, C2-C6alkenyl, aryl, phenyl or heteroaryl, or phenyl, aryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
or of a compound of formula XXI

OG Complex Work Unit Drawing
wherein Z7 is oxygen, sulfur, S═O, SO2 or CH2, R113 and R114 are each independently of the other hydrogen, halogen or C1-C4alkyl, W2 and W3 are each independently of the other CH2COOR115 or COOR0115 or together are a group of formula —(CH2)C(O)—O—C(O)—(CH2)—, and R115 and R0115 are each independently of the other hydrogen, C1-C4alkyl, C2-C4alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C4haloalkyl, or a metal cation or an ammonium cation;
or of a compound of formula XXII

OG Complex Work Unit Drawing
wherein R119 and R120 are each independently of the other hydrogen, halogen or C1-C4haloalkyl, R121 is hydrogen, C1-C4alkyl, C3-C4alkenyl, C3-C4alkynyl, C1-C4haloalkyl, C3-C6cycloalkyl, a metal cation or an ammonium cation, Z8 is N, CH, C—F or C—Cl and W4 is a group of formula

OG Complex Work Unit Drawing
wherein R122 and R123 are each independently of the other hydrogen or C1-C4alkyl and R124 and R125 are each independently of the other hydrogen or C1-C4alkyl;
or of a compound of formula XXIII

OG Complex Work Unit Drawing
wherein R126 is hydrogen, cyano, halogen, C1-C4alkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxycarbonyl, C1-C4alkylthiocarbonyl, —NH—R128, —C(O)NH—R0128, aryl or heteroaryl, or aryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
R127 is hydrogen, cyano, nitro, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4thioalkyl; and
R128 and R0128 are each independently of the other C1-C4alkyl, C1-C4haloalkyl, C3-C4alkenyl, C3-C4alkynyl, C3-C4cycloalkyl, aryl or heteroaryl, or aryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, formyl, C1-C4alkylcarbonyl or C1-C4alkylsufonyl;
or of a compound of formula XXIV

OG Complex Work Unit Drawing
wherein R129 and R130 are each independently of the other hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, mono-C1-C8- or di-C1-C8-alkylamino, C3-C6cycloalkyl, C1-C4thioalkyl, phenyl or heteroaryl, R131 has the meanings of R129 and in addition is OH, NH2, halogen, di-C1-C4aminoalkyl, C1-C4alkylthio, C1-C4alkylsulfonyl or C1-C4alkoxycarbonyl, R132 has the meanings of R129 and in addition is cyano, nitro, carboxyl, C1-C4alkoxycarbonyl, di-C1-C4aminoalkyl, C1-C4alkylthio, C1-C4alkylsulfonyl, SO2—OH, i-C1-C4aminoalkylsulfonyl or C1-C4alkoxysulfonyl, R133 has the meanings of R129 and in addition is OH, NH2, halogen, di-C1-C4aminoalkyl, pyrrolidin-1-yl, piperidin-1-yl, morpholin-1-yl, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkoxycarbonyl, phenoxy, naphthoxy, phenylamino, benzoyloxy or phenylsulfonyloxy;
or of a compound of formula XXV

OG Complex Work Unit Drawing
wherein R134 is hydrogen, C4alkyl, C1-C4haloalkyl, C2-C4alkenyl, C2-C4alkynyl or C1-C4alkoxy-C1-C4alkyl, R135 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4alkoxy and R136 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4alkoxy, with the proviso that R135 and R136 are not simultaneously hydrogen,
or of formula XXVI

OG Complex Work Unit Drawing
wherein
R143 is hydrogen, an alkali metal cation, alkaline earth metal cation, sulfonium cation or ammonium cation or ethyl;
or of formula XXVII

OG Complex Work Unit Drawing
wherein R144 and R145 are each independently of the other hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl or C3-C6cycloalkyl;
R146 is hydrogen, halogen, C1-C4alkyl, C1-C6haloalkyl or C1-C6haloalkoxy;
R147 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4alkoxycarbonyl or nitro;
n1 is 0, 1, 2 or 3; and
m is 1 or 2;
or of formula XXVIII

OG Complex Work Unit Drawing
wherein
R148 is hydrogen, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylthio, C3-C8cycloalkyl, phenyl, phenyl-C1-C6alkyl or heteroaryl; wherein the said groups may be substituted by halogen, cyano, nitro, amino, hydroxy, carbonyl, carboxyl, formyl, carbonamide or by sulfonamide;
R149 is hydrogen, C1-C6alkyl or C1-C4haloalkyl;
each R150 is independently of any other(s) hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, cyano, nitro, formyl or carboxyl;
R151 is hydrogen, C1-C6alkyl or C1-C4haloalkyl;
each R152 is independently of any other(s) hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, cyano, nitro, formyl or carboxyl;
o is 0, 1, or 2, and
p is 0, 1 or 2;
or of formula XXIX

OG Complex Work Unit Drawing
wherein
R159 is hydrogen, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, phenyl-C1-6alkylcarbonyl, phenylcarbonyl, C1-6alkylsulfonyl, C1-6alkenylsulfonyl or phenylsulfonyl, wherein the afore-mentioned hydrocarbon groups may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
R153 is hydrogen, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, C3-8cycloalkyl, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, C1-6alkylsulfonyl, C1-6alkenylsulfonyl or phenylsulfonyl, wherein the afore-mentioned hydrocarbon groups may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
R154 is hydrogen, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, C3-8cycloalkyl, formyl, C1-6alkylcarbonyl, C1-6alkenylcarbonyl, C1-6alkynylcarbonyl, C1-6alkoxycarbonyl, C1-6alkylthiocarbonyl, C3-8cycloalkylcarbonyl, C1-6alkylsulfonyl, C1-6alkenylsulfonyl or phenylsulfonyl, wherein the afore-mentioned hydrocarbon groups may be substituted by one or more halogen atoms, cyano, nitro, amino, methoxy, ethoxy or phenyl;
R155, R156, R157, and R158 are each independently of the others hydrogen, halogen, amino, C1-3alkylamino, C1-6dialkylamino, hydroxy, cyano, nitro, formyl, carboxyl, C1-6alkoxy, C1-6haloalkoxy, C1-6alkylcarbonyl, C1-6alkoxycarboxyl, C1-6alkyl, C1-6haloalkyl, C1-6alkenyl or C1-6alkynyl;
or R153 and R158, together with the ring atoms to which they are bonded, form a five- or six-membered, partially saturated or unsaturated ring that may contain up to 2 identical or different hetero atoms from the group oxygen, sulfur and nitrogen, it being possible for that ring to be substituted by an oxo radical.