Herbicidal derivatives

Abstract

Compounds of Formula (I) wherein the substituents are as defined in claim 1. The invention further relates to herbicidal compositions which comprise a compound of Formula (I) and to the use of compounds of Formula (I) for controlling weeds, in particular in crops of useful plants.

Description

[0001] 111607-FF 1 HERBICIDAL DERIVATIVESThe present invention relates to herbicidal indazole derivatives, e.g., as active ingredients, whichhave herbicidal activity. The invention also relates to agrochemical compositions which comprise at leastone of the indazole derivatives, to processes of preparation of these compounds and to uses of theindazole derivatives or compositions in agriculture or horticulture for controlling weeds, in particular incrops of useful plants. EP0448206 describes herbicidally active benzimidazole and indazole compounds. According to the present invention, there is provided a compound of Formula (I): wherein Z is Z1or Z2: Z1 Z2; R1is hydrogen or halogen; R2is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxyC1-C6alkyl, carboxyC1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl,C3-C6cycloalkylC2-C6alkynyl, C1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkoxyC1-C6alkylcarbonylC1-C6alkyl,C1-C6alkoxyC1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkoxycarbonylC1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkylcarbonyloxyC1-C6alkyl, C1-C6alkylaminocarbonylC1-C6alkyl, N,N-di(C1-C6alkyl)aminocarbonylC1-C6alkyl, (Ra)(Rb)C=NCO2C1-C3alkyl, N,N-di(C1-C6alkyl)aminooxycarbonylC1-C6alkyl, C1-C6alkoxycarbonylC1-C6haloalkyl, cyanoC1-C6alkyl, C1-C6alkylsulfonylC1-C6alkyl, phenyl, phenylC1-C3alkyl, phenylC2-C6alkenyl, phenylC2-C6alkynyl, phenylcarbonyloxyC1-C3alkyl, heterocyclyl,heterocyclylC1-C3alkyl, wherein each heterocyclyl moiety is a 4-, 5- or 6-membered non-aromaticmonocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S,heteroarylcarbonylC1-C3alkyl, or heteroarylC1-C3alkyl, wherein each heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and 111607-FF 2 S, and wherein the phenyl, heterocyclyl and heteroaryl moieties may be optionally substituted with 1, 2, 3, or 4 groups, which may be the same or different, represented by R4; R3 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxyC1-C6alkyl, C1-C6alkylcarbonyloxyC1-C6alkyl, C1- C6alkylaminocarbonylC1-C6alkyl, N,N-di(C1-C6alkyl)aminocarbonylC1-C6alkyl, cyanoC1-C6alkyl, C1-C6alkylsulfonylC1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, phenyl, phenylC1-C3alkyl,heterocyclyl, heterocyclylC1-C3alkyl, wherein each heterocyclyl moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S,heteroaryl, or heteroarylC1-C3alkyl, wherein each heteroaryl moiety is a 5- or 6-membered aromatic ringwhich comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S; R4is halogen, cyano, nitro, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylsulfanyl, C3-C6cycloalkyl, or C1-C6alkoxycarbonyl; andRaand Rbare each independently C1-C6alkyl; or an N-oxide thereof. Surprisingly, it has been found that the novel compounds of Formula (I) have, for practicalpurposes, a very advantageous level of herbicidal activity.A problem with many current herbicides used to control unwanted vegetation before planting a crop is that they can cause damage to the following crop if it is planted soon after the herbicide is used. A herbicide that is safe to crops when applied before they emerge, whilst providing good control on already emerged weeds, is therefore a major advantage over current herbicides. Surprisingly, it has been found that the novel compounds of Formula (I) may not only have, forpractical purposes, an advantageous level of herbicidal activity, but they also show no or low levels ofdamage to several major agricultural crops, such as soy (Glycine max), when applied pre-emergencewhilst providing control of unwanted vegetation (weeds and volunteer crops) when applied post-emergence, thus enabling them to be used successfully shortly before planting a new crop. In contrastrelated compounds reported in the prior art, whilst showing similar control of unwanted vegetation, cause unacceptable damage to many crops thus preventing their use. According to a second aspect, there is provided an agrochemical composition comprising aherbicidally effective amount of a compound of Formula (I) according to the present invention. Such anagricultural composition may further comprise at least one additional active ingredient and / or an agrochemically-acceptable diluent or carrier. According to a third aspect, there is provided a method of controlling weeds at a locus comprising applying to the locus a weed controlling amount of a composition comprising a compound of Formula (I). 111607-FF 3 According to a fourth aspect, there is provided the use of a compound of Formula (I) as a herbicide. Where substituents are indicated as being “optionally substituted”, this means that they may ormay not carry one or more identical or different substituents, e.g., one, two or three R4 substituents. Forexample, C1-C6alkyl substituted by 1, 2 or 3 halogens, may include, but not be limited to, -CH2Cl, -CHCl2,-CCl3, -CH2F, -CHF2, -CF3, -CH2CF3 or -CF2CH3 groups. As another example, C1-C6alkoxy substitutedby 1, 2 or 3 halogens, may include, but not limited to, CH2ClO-, CHCl2O-, CCl3O-, CH2FO-, CHF2O-,CF3O-, CF3CH2O- or CH3CF2O- groups.As used herein, the term “cyano” means a -CN group. As used herein, the term "halogen" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo)or iodine (iodo).As used herein, the term “nitro” means an -NO2group. As used herein, the term “acetyl” means a -C(O)CH3 group. As used herein, =O means an oxo group, e.g., as found in a carbonyl (-C(=O)-) group. As used herein, the term “carboxy” refers to an HO(O)C- group.As used herein, the term "C1-C6alkyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from one to six carbon atoms, and which is attached to the rest of the molecule by a single bond. “C1-C4alkyl” and “C1- C3alkyl” are to be construed accordingly. Examples of C1-C6alkyl include, but are not limited to, methyl,ethyl, n-propyl, and the isomers thereof, for example, isopropyl. A “C1-C6alkylene” group refers to thecorresponding definition of C1-C6alkyl, except that such radical is attached to the rest of the molecule by two single bonds. The term “C1-C2alkylene” is to be construed accordingly. Examples of C1-C6alkylene,include, but are not limited to, -CH2-, -CH2CH2- and -(CH2)3-.As used herein, the term “C1-C6haloalkyl” refers a C1-C6alkyl radical as generally defined abovesubstituted by one or more of the same or different halogen atoms. The terms “C1-C4haloalkyl” and “C1-C3haloalkyl”, are to be construed accordingly. Examples of C1-C6haloalkyl include, but are not limited totrifluoromethyl. As used herein, the term "C1-C6alkoxy" refers to a radical of the formula -ORawhere Rais a C1- C6alkyl radical as generally defined above. The terms “C1-C4alkoxy” and “C1-C3alkoxy” are to be construed accordingly. Examples of C1-C6alkoxy include, but are not limited to, methoxy, ethoxy, 1- methylethoxy (iso-propoxy), and propoxy. As used herein, the term "C2-C6alkenyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one double bond that can beof either the (E)- or (Z)-configuration, having from two to six carbon atoms, which is attached to the restof the molecule by a single bond. The term "C2-C3alkenyl" is to be construed accordingly. Examples ofC2-C6alkenyl include, but are not limited to, ethenyl (vinyl), prop-1-enyl, prop-2-enyl (allyl), but-1-enyl. As used herein, the term "C2-C6alkynyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from two to six carbon atoms, and which is attached to the rest of the molecule by a single bond. The term 111607-FF 4"C2-C3alkynyl" is to be construed accordingly. Examples of C2-C6alkynyl include, but are not limited to,ethynyl, prop-1-ynyl, but-1-ynyl. As used herein, the term “C2-C6haloalkenyl” refers to a C2-C6alkenyl moiety as defined abovesubstituted by one or more of the same or different halogen atoms. Examples of C2-C6alkenyl include,but are not limited to, 3-fluoroallyl, 3-bromoallyl, and 3-chloroallyl.As used herein, the term “C2-C6haloalkynyl” refers to a C2-C6alkynyl substituted by one or moreof the same or different halogen atoms. Examples of C2-C6alkynyl include, but are not limited to, 1-fluoroprop-1-ynyl, bromoprop-1-ynyl, and 1-chloroprop-1-ynyl, As used herein, the term “C1-C6alkoxyC1-C6alkyl” refers to a radical of the formula RbORa- whereinRb is a C1-C6alkyl radical as generally defined above, and Ra is a C1-C6alkylene radical as generallydefined above. The term “C1-C4alkoxyC1-C4alkyl” is to be construed accordingly.As used herein, the term “C3-C6cycloalkyl” refers to a radical which is a monocyclic saturated ringsystem which contains 3 to 6 carbon atoms. The terms "C3-C5cycloalkyl" and "C3-C4cycloalkyl" are tobe construed accordingly. Examples of C3-C6cycloalkyl include, but are not limited to, cyclopropyl,cyclobutyl, cyclopentyl, and cyclohexyl.As used herein, the term “C3-C6cycloalkylC1-C6alkyl” refers to a C3-C6cycloalkyl ring attached tothe rest of the molecule by a C1-C6alkylene linker as defined above. Examples of C3-C6cycloalkylC1-C6alkyl include, but are not limited to, cyclopropylmethyl. As used herein, the term “C3-C6cycloalkylC2-C6alkynyl” refers to a C3-C6cycloalkyl moiety asdefined above attached to the rest of the molecule by a C2-C6alkenyl chain as defined above.As used herein, the term “C1-C6alkoxycarbonyl” refers to a radical of the formula -C(O)ORa,wherein Ra is a C1-C6alkyl radical as generally defined above.As used herein, the term “carboxyC1-C6alkyl” refers to a carboxy radical as defined above, linkedto the rest of the molecule through a C1-C6alkylene linker as defined above.As used herein, the term “C1-C6alkoxycarbonylC1-C6alkyl” refers to a radical of the formulaRaOC(O)Rb-, wherein Ra is a C1-C6alkyl radical as generally defined above, and Rb is a C1-C6alkylenelinker as defined above. As used herein, the term “C1-C6alkylcarbonyloxyC1-C6alkyl” refers to a radical of the formulaRaC(O)ORb-, wherein Ra is a C1-C6alkyl radical as generally defined above, and Rb is a C1-C6alkylenelinker as defined above. As used herein, the term “C1-C6alkylaminocarbonyl” refers to a radical of the formula -C(O)NHRa,wherein Ra is a C1-C6alkyl radical as generally defined above. Examples of C1-C6alkylaminocarbonylinclude, but are not limited to, ethylcarbamoyl (i.e., ethylaminocarbonyl). As used herein, the term “C1-C6alkylaminocarbonylC1-C6alkyl” refers to a C1-C6alkylaminocarbonyl group as defined above attached to the rest of the molecule through a C1- C6alkylene linker as defined above. As used herein, the term “N,N-di(C1-C6alkyl)aminocarbonyl“ refers to a radical of the formula -C(O)N(Ra)(Rb), wherein Ra and Rb are each individually a C1-C6alkyl radical as generally defined above.The terms “N,N-di(C1-C4alkyl)aminocarbonyl” and “N,N-di(C1-C3alkyl)aminocarbonyl” are to beconstrued accordingly. Examples of N,N-di(C1-C6alkyl)aminocarbonyl include, but are not limited to,dimethylcarbamoyl (i.e., N,N-di(methyl)aminocarbonyl). 111607-FF 5 As used herein, the term “N,N-di(C1-C6alkyl)aminocarbonylC1-C6alkyl” refers to a N,N-di(C1-C6alkyl)aminocarbonyl group as defined above attached to the rest of the molecule through a C1- C6alkylene linker as defined above. As used herein, the term “N,N-di(C1-C6alkyl)aminooxycarbonylC1-C6alkyl” refers to a radical ofthe formula N(Ra)(Rb)OC(O)Rc-, wherein Ra and Rb are each individually a C1-C6alkyl radical asgenerally defined above, and Rc is a C1-C6alkylyne linker as defined above. As used herein, the term “C1-C6alkoxycarbonylC1-C6haloalkyl” refers to a radical of the formulaRaOC(O)Rb-, wherein Ra is a C1-C6alkyl radical as generally defined above, and Rb is a C1-C6alkylenelinker as defined above, and wherein the C1-C6alkylene linker is substituted by one or more of the same or different halogen atoms. As used herein, the term “C1-C6alkoxyC1-C6alkylcarbonylC1-C6alkyl” refers to a radical of theformula RaORbC(O)Rc-, wherein Ra and Rb are C1-C6alkyl radicals as generally defined above, and Rcis a C1-C6alkylene linker as defined above.As used herein, the term “C1-C6alkoxyC1-C6alkoxycarbonylC1-C6alkyl” refers to a radical of theformula RaORbOC(O)Rc-, wherein Ra and Rb are C1-C6alkyl radicals as generally defined above, and Rcis a C1-C6alkylene linker as defined above.As used herein, the term “C1-C6alkoxycarbonylC1-C6alkoxycarbonylC1-C6alkyl” refers to a radicalof the formula RaOC(O)RbOC(O)Rc-, wherein Ra and Rb are C1-C6alkyl radicals as generally definedabove, and Rc is a C1-C6alkylene linker as defined above.As used herein, the term “phenylcarbonyloxyC1-C3alkyl” refers to a radical of the formulaRaCO2Rb-, wherein Ra is a phenyl group and Rb is a C1-C6alkylene linker as defined above.As used herein, the term “cyanoC1-C6alkyl” refers to a C1-C6alkyl group as defined abovesubstituted with one or more cyano groups as defined above. Examples of cyanoC1-C6alkyl include, but are not limited to, cyanomethyl. As used herein, the term “C1-C6alkylsulfanyl“ refers to a radical of the formula -SRa, where Ra isa C1-C6alkyl radical as generally defined above. The terms “C1-C4alkylsulfanyl” and “C1-C3alkylsulfanyl”,are to be construed accordingly. Examples of C1-C6alkylsulfanyl include, but are not limited tomethylsulfanyl. As used herein, the term “C1-C6alkylsulfonylC1-C6alkyl” refers to a C1-C6alkylsulfonyl group asdefined above attached to the rest of the molecule through a C1-C3alkylene linker as defined above. As used herein, the term “phenylC1-C3alkyl” refers to a phenyl ring attached to the rest of themolecule through a C1-C3alkylene linker as defined above. The term phenylC1-C2alkyl is to beconstrued accordingly. As used herein, the term “phenylC2-C6alkenyl” refers to a phenyl ring attached to the rest of the molecule through a C2-C6alkenyl linker as defined above. As used herein, the term “phenylC2-C6alkynyl” refers to a phenyl ring attached to the rest of themolecule through a C2-C6alkynyl linker as defined above.As used herein, the term "heterocyclyl" refers to a stable 4-, 5- or 6-membered non-aromaticmonocyclic ring which comprises 1, 2 or 3 heteroatoms, wherein the heteroatoms are individuallyselected from nitrogen, oxygen, and sulfur. The heterocyclyl radical may be bonded to the rest of themolecule via a carbon atom or heteroatom. Examples of heterocyclyl include, but are not limited to, 111607-FF 6 aziridinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuryl, pyrrolidinyl, pyrazolidinyl, imidazolidnyl, piperidinyl, piperazinyl, morpholinyl, dioxolanyl, dithiolanyl and thiazolidinyl. As used herein, the term “heterocyclylC1-C3alkyl” refers to a heterocyclyl moiety as defined aboveattached to the rest of the molecule through a C1-C3alkylene chain as defined above. Examples ofheterocyclylC1-C3alkyl include, but are not limited to heterocyclylmethyl, wherein the heterocyclyl moietyis attached to the rest of the molecule through a -CH2- linker.As used herein, the term “heteroaryl” refers to a 5- or 6-membered aromatic monocyclic ringradical which comprises 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen, and sulfur.Examples of heteroaryl include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl or pyridyl. As used herein, the term “heteroarylC1-C3alkyl” refers to a heteroaryl moiety as defined aboveattached to the rest of the molecule through a C1-C3alkylene chain as defined above. Examples ofheteroarylC1-C3alkyl include, but are not limited to heteroarylmethyl, wherein the heterocyclyl moiety isattached to the rest of the molecule through a -CH2- linker.As used herein, the term “heteroarylcarbonylC1-C3alkyl” refers to a radical of the formulaRaC(O)Rb-, wherein Ra is a heteroaryl radical as generally defined above, and Rb is a C1-C6alkylenelinker as defined above. The presence of one or more possible stereogenic elements in a compound of formula (I) meansthat the compounds may occur in optically isomeric forms, i.e., enantiomeric or diastereomeric forms.Also, atropisomers may occur as a result of restricted rotation about a single bond. Formula (I) isintended to include all those possible isomeric forms and mixtures thereof. The present invention includes all those possible isomeric forms and mixtures thereof for a compound of formula (I). Likewise,formula (I) is intended to include all possible tautomers. The present invention includes all possibletautomeric forms for a compound of formula (I). In each case, the compounds of formula (I) according to the invention are in free form, in oxidizedform as an N-oxide, or in salt form, e.g., an agronomically usable salt form. Salts that the compounds ofFormula (I) may form with amines, including primary, secondary and tertiary amines (for exampleammonia, dimethylamine and triethylamine), alkali metal and alkaline earth metal bases, transitionmetals or quaternary ammonium bases are preferred. In a particularly preferred set of embodiments,the compounds of Formula (I) may form chloride or 2,2,2-trifluoroacetate salts.N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing heteroaromatic compounds. They are described for instance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton (1991). The following list provides definitions, including preferred definitions, for substituents Z,R1, R2, R3, R4, Ra, and Rb, with reference to compounds of Formula (I). For any one of thesesubstituents, any of the definitions given below may be combined with any definition of any othersubstituent given below or elsewhere in this document. 111607-FF 7 Z is Z1or Z2. In one embodiment, Z is Z1. In another embodiment, Z is Z2. R1 is hydrogen or halogen. Preferably, R1 is hydrogen, fluoro, or chloro. More preferably, R1 ishydrogen or fluoro. In one aspect, R1is hydrogen. In another aspect, R1is fluoro. R2is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2- C6haloalkynyl, C1-C6alkoxyC1-C6alkyl, carboxyC1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkylC2-C6alkynyl, C1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkoxyC1-C6alkylcarbonylC1-C6alkyl, C1-C6alkoxyC1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkoxycarbonylC1-C6alkoxycarbonylC1-C6alkyl, C1- C6alkylcarbonyloxyC1-C6alkyl, C1-C6alkylaminocarbonylC1-C6alkyl, N,N-di(C1-C6alkyl)aminocarbonylC1-C6alkyl, (Ra)(Rb)C=NCO2C1-C3alkyl, N,N-di(C1-C6alkyl)aminooxycarbonylC1-C6alkyl, C1-C6alkoxycarbonylC1-C6haloalkyl, cyanoC1-C6alkyl, C1-C6alkylsulfonylC1-C6alkyl, phenyl, phenylC1-C3alkyl, phenylC2-C6alkenyl, phenylC2-C6alkynyl, phenylcarbonyloxyC1-C3alkyl, heterocyclyl,heterocyclylC1-C3alkyl, wherein each heterocyclyl moiety is a 4-, 5- or 6-membered non-aromaticmonocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S,heteroarylcarbonylC1-C3alkyl, or heteroarylC1-C3alkyl, wherein each heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and wherein the phenyl, heterocyclyl and heteroaryl moieties may be optionally substituted with 1, 2, 3, or 4 groups, which may be the same or different, represented by R4. Preferably, R2is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2- C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxyC1-C6alkyl, carboxyC1-C6alkyl, C3-C6cycloalkyl, C3- C6cycloalkylC1-C6alkyl, C3-C6cycloalkylC2-C4alkynyl, C1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkoxyC1- C4alkylcarbonylC1-C4alkyl, C1-C6alkoxyC1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkoxycarbonylC1- C6alkoxycarbonylC1-C6alkyl, C1-C4alkylcarbonyloxyC1-C4alkyl, C1-C4alkylaminocarbonylC1-C4alkyl,N,N-di(C1-C4alkyl)aminocarbonylC1-C4alkyl, (Ra)(Rb)C=NCO2C1-C3alkyl, N,N-di(C1-C6alkyl)aminooxycarbonylC1-C4alkyl, C1-C6alkoxycarbonylC1-C6haloalkyl, cyanoC1-C6alkyl, C1-C6alkylsulfonylC1-C4alkyl, phenyl, phenylC1-C3alkyl, phenylC2-C4alkenyl, phenylC2-C4alkynyl,phenylcarbonyloxyC1-C3alkyl, heterocyclyl, heterocyclylC1-C3alkyl, wherein each heterocyclyl moiety isa 4-, 5- or 6-membered non-aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individuallyselected from N, O and S, heteroarylcarbonylC1-C3alkyl, or heteroarylC1-C3alkyl, wherein eachheteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, or 3 heteroatomsindividually selected from N, O and S, and wherein the phenyl, heterocyclyl and heteroaryl moieties maybe optionally substituted with 1, 2, or 3 groups, which may be the same or different, represented by R4.More preferably, R2is hydrogen, C1-C6alkyl, C1-C4haloalkyl, C2-C5alkenyl, C2-C4haloalkenyl, C2- C6alkynyl, C2-C5haloalkynyl, C1-C6alkoxyC1-C4alkyl, carboxyC1-C4alkyl, C3-C6cycloalkyl, C3- C6cycloalkylC1-C4alkyl, C3-C6cycloalkylC2-C4alkynyl, C1-C6alkoxycarbonylC1-C6alkyl, C1-C4alkoxyC1- C4alkylcarbonylC1-C4alkyl, C1-C4alkoxyC1-C4alkoxycarbonylC1-C4alkyl, C1-C6alkoxycarbonylC1- C6alkoxycarbonylC1-C6alkyl, C1-C4alkylcarbonyloxyC1-C3alkyl, C1-C4alkylaminocarbonylC1-C3alkyl,N,N-di(C1-C3alkyl)aminocarbonylC1-C3alkyl, (Ra)(Rb)C=NCO2C1-C3alkyl, N,N-di(C1- 111607-FF 8C6alkyl)aminooxycarbonylC1-C3alkyl, C1-C4alkoxycarbonylC1-C4haloalkyl, cyanoC1-C4alkyl, C1-C4alkylsulfonylC1-C3alkyl, phenyl, phenylC1-C2alkyl, phenylC2-C3alkenyl, phenylC2-C3alkynyl,phenylcarbonyloxyC1-C2alkyl, heterocyclyl, heterocyclylC1-C2alkyl, wherein each heterocyclyl moiety isa 5- or 6-membered non-aromatic monocyclic ring comprising 1 or 2 heteroatoms individually selectedfrom N, O and S, heteroarylcarbonylC1-C2alkyl, or heteroarylC1-C2alkyl, wherein each heteroaryl moietyis a 5- or 6-membered aromatic ring which comprises 1 or 2 heteroatoms individually selected from N,O and S, and wherein the phenyl, heterocyclyl and heteroaryl moieties may be optionally substitutedwith 1 or 2 groups, which may be the same or different, represented by R4.More preferably still, R2is C1-C6alkyl, C1-C4haloalkyl, C2-C5alkenyl, C2-C6alkynyl, C2- C5haloalkynyl, C1-C6alkoxyC1-C4alkyl, carboxyC1-C4alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C4alkyl, C1-C6alkoxycarbonylC1-C6alkyl, C1-C4alkoxyC1-C4alkoxycarbonylC1-C4alkyl, C1-C6alkoxycarbonylC1-C6alkoxycarbonylC1-C6alkyl, (Ra)(Rb)C=NCO2C1-C3alkyl, N,N-di(C1-C6alkyl)aminooxycarbonylC1-C3alkyl, C1-C4alkoxycarbonylC1-C4haloalkyl, cyanoC1-C4alkyl, phenylcarbonyloxyC1-C2alkyl, andwherein each phenyl moiety may be optionally substituted with a single R4 group.Even more preferably, R2is C1-C4alkyl, C1-C3haloalkyl, C2-C3alkenyl, C2-C4alkynyl, C2- C4haloalkynyl, C1-C4alkoxyC1-C3alkyl, carboxyC1-C3alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C3alkyl, C1-C4alkoxycarbonylC1-C3alkyl, C1-C3alkoxyC1-C3alkoxycarbonylC1-C3alkyl, C1-C3alkoxycarbonylC1-C3alkoxycarbonylC1-C3alkyl, (Ra)(Rb)C=NCO2C1-C2alkyl, N,N-di(C1-C3alkyl)aminooxycarbonylC1-C2alkyl, C1-C3alkoxycarbonylC1-C3haloalkyl, cyanoC1-C3alkyl, phenylcarbonyloxyC1-C2alkyl, andwherein each phenyl moiety may be optionally substituted with a single R4group. Even more preferably still, R2 is C2-C4alkynyl or C1-C4alkoxycarbonylC1-C3alkyl. In a particularly,R2 is C3alkynyl or C2alkoxycarbonylC2alkyl. Most preferably, R2 is prop-2-ynyl or ethoxycarbonyl-1-methylmethyl. R3is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2- C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxyC1-C6alkyl, C1-C6alkylcarbonyloxyC1-C6alkyl, C1- C6alkylaminocarbonylC1-C6alkyl, N,N-di(C1-C6alkyl)aminocarbonylC1-C6alkyl, cyanoC1-C6alkyl, C1-C6alkylsulfonylC1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, phenyl, phenylC1-C3alkyl,heterocyclyl, heterocyclylC1-C3alkyl, wherein each heterocyclyl moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S,heteroaryl, or heteroarylC1-C3alkyl, wherein each heteroaryl moiety is a 5- or 6-membered aromatic ringwhich comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S. Preferably, R3is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C2-C4alkenyl, C2- C4haloalkenyl, C2-C4alkynyl, C2-C4haloalkynyl, C1-C4alkoxyC1-C3alkyl, C1-C4alkylcarbonyloxyC1- C3alkyl, C1-C4alkylaminocarbonylC1-C3alkyl, N,N-di(C1-C4alkyl)aminocarbonylC1-C3alkyl, cyanoC1-C4alkyl, C1-C4alkylsulfonylC1-C3alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C3alkyl, phenyl, phenylC1-C3alkyl, heterocyclyl, heterocyclylC1-C3alkyl, wherein each heterocyclyl moiety is a 5- or 6-memberednon-aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, 111607-FF 9heteroaryl, or heteroarylC1-C3alkyl, wherein each heteroaryl moiety is a 5- or 6-membered aromatic ringwhich comprises 1, 2, or 3 heteroatoms individually selected from N, O and S. More preferably, R3is hydrogen, halogen, cyano, C1-C6alkyl, C1-C4haloalkyl, C2-C3alkenyl, C2- C3haloalkenyl, C2-C3alkynyl, C2-C3haloalkynyl, C1-C3alkoxyC1-C3alkyl, C1-C4alkylcarbonyloxyC1- C3alkyl, C1-C3alkylaminocarbonylC1-C2alkyl, N,N-di(C1-C3alkyl)aminocarbonylC1-C2alkyl, cyanoC1-C3alkyl, C1-C2alkylsulfonylC1-C2alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C2alkyl, phenyl, phenylC1-C2alkyl, heterocyclyl, heterocyclylC1-C2alkyl, wherein each heterocyclyl moiety is a 5- or 6-memberednon-aromatic monocyclic ring comprising 1 or 2 heteroatoms individually selected from N, O and S,heteroaryl, or heteroarylC1-C3alkyl, wherein each heteroaryl moiety is a 5- or 6-membered aromatic ringwhich comprises 1, 2, or 3 heteroatoms individually selected from N and O.In one embodiment, R3is hydrogen, halogen, cyano, or C1-C6alkyl. In a further embodiment, R3is halogen, preferably chloro or fluoro, and more preferably, chloro. R4is halogen, cyano, nitro, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylsulfanyl, C3-C6cycloalkyl, or C1- C6alkoxycarbonyl. Preferably, R4is halogen, cyano, nitro, C1-C4alkyl, C1-C4alkoxy, C1-C3alkylsulfanyl,C3-C6cycloalkyl, or C1-C3alkoxycarbonyl. More preferably still, R4 is halogen, cyano, nitro, C1-C3alkyl, orC1-C3alkoxy. Raand Rbare each independently C1-C6alkyl. Preferably, Raand Rbare each independently C1- C4alkyl, more preferably, Raand Rbare each independently C1-C3alkyl. In one set of embodiments, Raand Rbare both methyl. In a compound of formula (I) according to the present invention, preferably: Z is Z1or Z2; R1 is hydrogen or halogen;R2 is C1-C6alkyl, C1-C4haloalkyl, C2-C5alkenyl, C2-C6alkynyl, C2-C5haloalkynyl, C1-C6alkoxyC1-C4alkyl, carboxyC1-C4alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C4alkyl, C1-C6alkoxycarbonylC1- C6alkyl, C1-C4alkoxyC1-C4alkoxycarbonylC1-C4alkyl, C1-C6alkoxycarbonylC1- C6alkoxycarbonylC1-C6alkyl, (Ra)(Rb)C=NCO2C1-C3alkyl, N,N-di(C1-C6alkyl)aminooxycarbonylC1-C3alkyl, C1-C4alkoxycarbonylC1-C4haloalkyl, cyanoC1-C4alkyl,phenylcarbonyloxyC1-C2alkyl, and wherein each phenyl moiety may be optionally substituted with asingle R4 group; andR3is halogen; R4 is halogen, cyano, nitro, or C1-C3alkyl; andRa and Rb are both methyl.In a compound of formula (I) according to the present invention, preferably: Z is Z1or Z2; R1is hydrogen or fluoro; R2 is C3alkynyl or C2alkoxycarbonylC2alkyl; and 111607-FF 10 R3is chloro or fluoro. Compounds of the invention can be made as shown in the following schemes, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of Formula (I). General methods for the production of compounds of Formula (I) are described below. Unless otherwisestated in the text, R1, R2, and R3, are as defined hereinbefore. The starting materials used for thepreparation of the compounds of the invention may be purchased from usual commercial suppliers or may be prepared by known methods. The starting materials as well as the intermediates may be purified before use in the next step by state of the art methodologies such as chromatography, crystallisation, distillation and filtration. Scheme 1: Compounds of formula (A) may be prepared, as shown in Scheme 1 above, by reaction ofcompounds of formula (B) with phenyl N-methyl-N-(methylcarbamothioyl)carbamate in the presence of a base, such as sodium acetate, in a suitable solvent, such as N,N-dimethylformamide, optionally at an elevated temperature (for example 60 °C). Scheme 2: Compounds of formula (B) may be obtained, as shown in Scheme 2 above, by treatment ofcompounds of formula (C) with phenyl chloroformate in the presence of a base, such as sodium bicarbonate, in a solvent such as ethyl acetate with an optional co-solvent (such as water). Scheme 3: 111607-FF 11 Compounds of formula (D) may be obtained, as shown in Scheme 3 above, by treatment ofcompounds of formula (E) with a base, such as potassium carbonate, and a methylating reagent, suchas methyl iodide, in a solvent such as N,N-dimethylformamide. Scheme 4: Compounds of formula (E) may be obtained, as shown in Scheme 4 above, by treatment ofcompounds of formula (F) with compounds of formula (G) in the presence of an acid, such as aceticacid. The reaction may be performed at elevated temperatures (for example 80°C). Scheme 5: Compounds of formula (F) may be prepared, as shown in Scheme 5 above, by reduction ofcompounds of formula (G) using an oxidisable metal (such as iron, zinc or tin(II)) optionally in the presence of an acid, such as HCl, or a salt such as ammonium chloride, in a solvent such as ethanol or ethyl acetate with an optional co-solvent such as water. Compounds of formula (G) may also be reducedto compounds of formula (B) under metal-free conditions, for example with tetrahydroxydiboron and 4,4'-bipyridine in a solvent such as N,N-dimethylformamide. 111607-FF 12 Scheme 6: Alternatively, compounds of formula (F) may be prepared, as shown in Scheme 6 above, byreaction of compounds of formula (H) with an acid, such as HCl or trifluoroacetic acid, in a solvent suchas ethanol or dichloromethane.Scheme 7: Compounds of formula (H) may be prepared, as shown in Scheme 7 above, by treatment ofcompounds of formula (J), wherein X represents halogen such as Br or I, with tert-butyl carbamate, ametal catalyst and ligand such as XPhos Pd G3, a base such as cesium carbonate, in a solvent suchas toluene. The reaction may be performed at elevated temperatures (for example 120°C).Scheme 8: Compounds of formula (J), wherein X represents NO2 or halogen, may be prepared as shownin Scheme 8 above by alkylation of a compound of formula (K) with an alkyl halide or pseudo-halide offormula (L), wherein X represents iodide, bromide, chloride, tosylate, mesylate or any other suitableleaving group. Typically the reaction is performed in the presence of a base, such as potassium or caesium carbonate, in a suitable solvent, such as acetonitrile or N,N-dimethylformamide. The reaction may be performed at room temperature or at elevated temperatures (for example 75°C). 111607-FF 13 Scheme 9: Compounds of formula (K) may be prepared as shown in Scheme 9 above by halogenation ofcompounds of formula (M), wherein X represents NO2 or halogen, with a chlorinating reagent, such asN-chlorosuccinimide, or a fluorinating reagent, such as 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), in a solvent such as acetonitrile, optionally with theaddition of an acid such as acetic acid. Compounds of formula (M) are commercially available or may be prepared by known methods. The present invention still further provides a method of controlling weeds at a locus said method comprising application to the locus of a weed controlling amount of a composition comprising a compound of Formula (I). Moreover, the present invention may further provide a method of selectivelycontrolling weeds at a locus comprising useful (crop) plants and weeds, wherein the method comprisesapplication to the locus of a weed controlling amount of a composition according to the present invention. ‘Controlling’ means killing, reducing or retarding growth or preventing or reducing germination. It is noted that the compounds of the present invention show an improved selectivity compared to known, structurally similar compounds. Generally the plants to be controlled are unwanted plants (weeds). ‘Locus’ means the area in which the plants are growing or will grow. The application may be applied to the locus pre-emergence and / or postemergence of the crop plant. Some crop plants may be inherently tolerant to herbicidal effects of compounds of Formula (I). The rates of application of compounds of Formula (I) may vary within wide limits and depend onthe nature of the soil, the method of application (pre- or post-emergence; seed dressing; application tothe seed furrow; no tillage application etc.), the crop plant, the weed(s) to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. The compounds of Formula I according to the invention are generally applied at a rate of from 10 to 2500 g / ha, especially from 25 to 1000 g / ha, more especially from 25 to 250 g / ha. The application is generally made by spraying the composition, typically by tractor mounted sprayer for large areas, but other methods such as dusting (for powders), drip or drench can also be used. The term "useful plants" is to be understood as also including useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides such as, for example, 4-Hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, ALS inhibitors, for example primisulfuron,prosulfuron and trifloxysulfuron, 5-enol-pyrovyl-shikimate-3-phosphate-synthase (EPSPS) inhibitors, glutamine synthetase (GS) inhibitors or protoporphyrinogen-oxidase (PPO) inhibitors as a result of 111607-FF 14 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 herbicidesor classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistantmaize varieties commercially available under the trade names RoundupReady®, Herculex I^ andLibertyLink®. The term "useful plants" is to be understood as also including useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus. Examples of such plants are: YieldGard^ (maize variety that expresses a CryIA(b) toxin);YieldGard Rootworm^ (maize variety that expresses a CryIIIB(b1) toxin); YieldGard Plus^ (maizevariety that expresses a CryIA(b) and a CryIIIB(b1) toxin); Starlink^ (maize variety that expresses aCry9(c) toxin); Herculex I^ (maize variety that expresses a CryIF(a2) toxin and the enzymephosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinateammonium); NuCOTN 33B^ (cotton variety that expresses a CryIA(c) toxin); Bollgard I^ (cotton varietythat expresses a CryIA(c) toxin); Bollgard II® (cotton variety that expresses a CryIA(c) and a CryIIA(b)toxin); VIPCOT^ (cotton variety that expresses a VIP toxin); NewLeaf^ (potato variety that expressesa CryIIIA toxin); NatureGard^ Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CBAdvantage (Bt11 corn borer (CB) trait), Agrisure® RW (corn rootworm trait) and Protecta^. Plant crops or seed material thereof can be both resistant to herbicides and, at the same time, resistant to insect feeding (“stacked” transgenic events). For example, seed can have the ability toexpress an insecticidal Cry3 protein while at the same time being tolerant to glyphosate.Crop plants are also to be understood to include those which are obtained by conventional methods of breeding or genetic engineering and contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour). The compounds of Formula (I) (or compositions comprising such) can be used to control unwanted plants (collectively, ‘weeds’). The weeds to be controlled may be both monocotyledonous species, for example Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitaria, Echinochloa, Eleusine, Lolium, Monochoria, Rottboellia, Sagittaria, Scirpus, Setaria and Sorghum, anddicotyledonous species, for example Abutilon, Amaranthus, Ambrosia, Chenopodium, Chrysanthemum,Conyza, Galium, Ipomoea, Nasturtium, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium. Compounds of Formula (I) may be used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation to provide herbicidal compositions, using formulation adjuvants, such as carriers, solvents and surface-active agents (SAA). The invention therefore further provides a herbicidal composition, comprising at least one compound Formula (I) and an agriculturally acceptable carrier and optionally an adjuvant. An agricultural acceptable carrier is for example a carrier that is suitable for agricultural use. Agricultural carriers are well known in the art. 111607-FF 15 The herbicidal compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1to 95 % by weight, compounds of Formula I and from 1 to 99.9 % by weight of a formulation adjuvantwhich preferably includes from 0 to 25 % by weight of a surface-active substance.The compositions can be chosen from a number of formulation types. These include an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a soluble powder (SP), a wettable powder (WP) and a soluble granule (SG). The formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of Formula (I). 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 111607-FF 16 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-C10 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 insolution (by dissolving it in an appropriate solvent) and then emulsifying the resultant liquid or solutioninto water containing one or more SAAs, 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 SAAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation. A compound of Formula (I) is present initially in either the water or the solvent / SAA 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 pesticides 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. 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. The composition 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 111607-FF 17 on treated surfaces; or uptake or mobility of a compound of Formula (I). Such additives include surface active agents (SAAs), spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), modified plant oils such as methylated rape seed oil (MRSO), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of Formula (I). Wetting agents, dispersing agents and emulsifying agents may be SAAs of the cationic, anionic, amphoteric or non-ionic type. Suitable SAAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts. Suitable anionic SAAs 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, butylnaphthalenesulphonate and mixtures of sodium di-isopropyl- and tri-isopropyl-naphthalene sulphonates), ethersulphates, 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 olefine sulphonates, taurates, lignosulphonates and phosphates / sulphates of tristyrylphenols. Suitable SAAs of the amphoteric type include betaines, propionates and glycinates. Suitable SAAs 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); lecithins and sorbitans and esters thereof, alkyl polyglycosides and tristyrylphenols. Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite). The compounds of present invention can also be used in mixture with one or more additional herbicides and / or plant growth regulators. Examples of such additional herbicides or plant growth regulators include acetochlor, acifluorfen (including acifluorfen-sodium), aclonifen, ametryn, amicarbazone, aminopyralid, aminotriazole, atrazine, beflubutamid-M, benquitrione, bensulfuron (including bensulfuron-methyl), bentazone, bicyclopyrone, bilanafos, bipyrazone, bispyribac-sodium, bixlozone, broclozone, bromacil, bromoxynil, butachlor, butafenacil, carfentrazone (including carfentrazone-ethyl), cloransulam (including cloransulam-methyl), chlorimuron (including chlorimuron- ethyl), chlorotoluron, chlorsulfuron, cinflubrolin, cinmethylin, clacyfos, clethodim, clodinafop (including clodinafop-propargyl), clomazone, clopyralid, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cyhalofop (including cyhalofop-butyl), cypyrafluone, 2,4-D (including the choline salt and 2-ethylhexyl ester 111607-FF 18 thereof), 2,4-DB, desmedipham, dicamba (including the aluminium, aminopropyl, bis- aminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts thereof) diclosulam, diflufenican, diflufenzopyr, dimesulfazet, dimethachlor, dimethenamid-P, dioxopyritrione, diquat dibromide, diuron, epyrifenacil, ethalfluralin, ethofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, feproxydim, flazasulfuron, florasulam, florpyrauxifen (including florpyrauxifen-benzyl), fluazifop (including fluazifop-P-butyl), flucarbazone (including flucarbazone-sodium), fluchloraminopyr (including fluchloraminopyr-tefuryl), flufenacet, flufenoximacil, flumetsulam, flumioxazin, fluometuron, flupyrsulfuron (including flupyrsulfuron-methyl-sodium), fluroxypyr (including fluroxypyr-meptyl), flusulfinam, fomesafen, foramsulfuron, glufosinate (including L-glufosinate and the ammonium salts of both), glyphosate (including the diammonium, isopropylammonium and potassium salts thereof), halauxifen (including halauxifen-methyl), haloxyfop (including haloxyfop-methyl), hexazinone, hydantocidin, icafolin (including icafolin-methyl), imazamox (including R-imazamox), imazapic, imazapyr, imazethapyr, indaziflam, indolauxipyr (including indolauxipyr-cyanomethyl), iodosulfuron (including iodosulfuron-methyl-sodium), iofensulfuron (including iofensulfuron-sodium), ioxynil, iptriazopyrid, isoproturon, isoxaflutole, lancotrione, MCPA, MCPB, mecoprop-P, mesosulfuron (including mesosulfuron-methyl), mesotrione, metamitron, metazachlor, methiozolin, metolachlor, metosulam, metribuzin, metproxybicyclone, metsulfuron, napropamide, nicosulfuron, norflurazon, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, phenmedipham, picloram, pinoxaden, pretilachlor, primisulfuron-methyl, prometryne, propanil, propaquizafop, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen (including pyraflufen- ethyl), pyraquinate, pyrasulfotole, pyridate, pyriftalid, pyriflubenzoxim, pyrimisulfan, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quizalofop (including quizalofop-P-ethyl and quizalofop-P-tefuryl), rimisoxafen, rimsulfuron, saflufenacil, sethoxydim, simazine, S-metalochlor, sulfentrazone, sulfosulfuron, tebuthiuron, tefuryltrione, tembotrione, terbuthylazine, terbutryn, tetflupyrolimet, thiencarbazone, thifensulfuron, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, tribenuron (including tribenuron-methyl), triclopyr, trifloxysulfuron (including trifloxysulfuron-sodium), trifludimoxazin, trifluralin, triflusulfuron, tripyrasulfone, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5- carboxylic acid ethyl ester, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin- 2-one, 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 5-ethoxy-4-hydroxy-1- methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2- pyridyl]imidazolidin-2-one, 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3- yl]imidazolidin-2-one, (4R)1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one, ethyl-2-[[3-[[3-chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-pyrimidin-1-yl]-2-pyridyl]oxy]-3-pyridyl]oxy]acetate, methyl 2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]-2-methoxy-acetate, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl- pyridazin-3-one, (2-fluorophenyl)methyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxy- phenyl)pyrimidine-4-carboxylate, 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxy-phenyl)pyrimidine- 4-carboxylic acid, methyl 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)- pyrimidinyl]-4-fluorophenyl]-3a,4,5,6-tetrahydro-6-methyl-6aH-cyclopent[d]isoxazole-6a-carboxylate, 111607-FF 19 (isopropylideneamino) 6-amino-2-(4-chloro-2-fluoro-3-methoxy-phenyl)-5-methoxy-pyrimidine-4- carboxylate and ethyl 2-[2-[[3-chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2- pyridyl]oxy]phenoxy]acetate. The compounds or mixtures of the present invention can also be used in combination with one or more herbicide safeners. Examples of such safeners include benoxacor, cloquintocet (including cloquintocet-mexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlorazole-ethyl), fenclorim, fluxofenim, furilazole, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr- diethyl), metcamifen and oxabetrinil. The mixing partners of the compound of Formula (I) may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, Sixteenth Edition, British Crop Protection Council, 2012. The mixing ratio of the compound of Formula (I) to the mixing partner is preferably from 1: 100 to 1000:1. 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). The compounds or mixtures of the present invention can also be used in combination with one or more herbicide safeners. Examples of such safeners include benoxacor, cloquintocet (including cloquintocet-mexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlorazole-ethyl), fenclorim, fluxofenim, furilazole, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr- diethyl), metcamifen and oxabetrinil. Particularly preferred are mixtures of a compound of Formula (I) with cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and / or metcamifen. The safeners of the compound of Formula (I) may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, 16thEdition (BCPC), 2012. The reference to cloquintocet-mexyl also applies to a lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium,quaternary ammonium, sulfonium or phosphonium salt thereof as disclosed in WO 02 / 34048.Preferably the mixing ratio of compound of Formula (I) to safener is from 100:1 to 1:10, especially from 20:1 to 1:1. The compounds of Formula (I) are normally used in the form of agrochemical compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g. fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non- selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation. The term “locus” as used herein means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation. The term “plants” refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits. The term “plant propagation material” is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings 111607-FF 20 or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably “plant propagation material” is understood to denote seeds. Pesticidal agents referred to herein using their common name are known, for example, from "The Pesticide Manual", 15th Ed., British Crop Protection Council 2009. The compounds of formula (I) may be used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end, they may be conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions,the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, arechosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects. Suitable carriers and adjuvants, e.g., for agricultural use, can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants,wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described inWO 97 / 33890. The compounds of Formula (I) are normally used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be, e.g., fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation. The compound of Formula (I) may be the sole active ingredient of a composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate. An additional active ingredient may, in some cases, result in unexpected synergistic activities. In general, the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% solid or liquid formulation inerts and adjuvant(s),the active agent consisting of at least the compound of formula (I) together with component (B) and (C),and optionally other active agents, particularly microbiocides or conservatives or the like. Concentrated forms of compositions generally contain in between about 2 and 80%, preferably between about 5 and 70% by weight of active agent. Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations. 111607-FF 21The tables below illustrate examples of individual compounds of Formula (I) according to the invention: Table 1: Individual compounds of Formula (I) according to the invention Cpd No. R2 Cpd No. R2001 Me 027 CH2CO2Et002 Et 028 CH2CO2nPr003 n-Pr 029 CH2CO2iPr004 i-Pr 030 CH2CO2nBu005 c-Pr 031 CH2CO2CH2CH2OMe006 n-Bu 032 CH2CO2CH2CO2Me007 sec-butyl 033 CH2CO2CH(Me)CO2Me008 i-Bu 034 CH2CO2N=CMe2009 CH2CH2F 035 CH2CO2Ph(4-NO2)010 CH2CHF2 036 CH(Me)CO2H011 CH2c-Pr 037 CH(Me)CO2Me012 CH2CH=CH2 038 CH(Me)CO2Et013 CH(Me)CH=CH2 039 CH(Me)CO2nPr014 CH2C(Me)=CH2 040 CH(Me)CO2iPr015 CH2CH=CHMe 041 CH(Me)CO2nBu016 CH2OMe 042 CH(Me)2CO2CH2CH2OMe017 CH(Me)OMe 043 CH(Me)CO2CH2CO2Me018 CH(Et)OMe 044 CH(Me)CO2CH(Me)CO2Me019 CH2CN 045 CH(Me)CO2N=CMe2020 CH(Me)CN 046 CH(Me)CO2Ph(4-NO2)021 CH2C≡CH 047 CH2CH2CO2Me022 CH(Me)C≡CH 048 CH2CH2CH2CO2Me023 CH2C≡CMe 049 CH2CONHMe024 CH2C≡CCl 050 CH2CONMe2025 CH2CO2H 051 CH(Me)CONHMe026 CH2CO2Me 052 CH(Me)CONMe2Table A-1 provides 52 compounds A-1.001 to A-1.052 of Formula (I) wherein Z is Z1, R1 is fluoro, R3 ischloro and R2 is defined in Table 1. 111607-FF 22Table A-2 provides 52 compounds A-2.001 to A-2.052 of Formula (I) wherein Z is Z1, R1 is fluoro, R3 isfluoro and R2 is defined in Table 1.Table A-3 provides 52 compounds A-3.001 to A-3.052 of Formula (I) wherein Z is Z1, R1 is fluoro, R3 ishydrogen and R2 is defined in Table 1.Table A-4 provides 52 compounds A-4.001 to A-4.052 of Formula (I) wherein Z is Z1, R1 is fluoro, R3 iscyano and R2is defined in Table 1.Table A-5 provides 52 compounds A-5.001 to A-5.052 of Formula (I) wherein Z is Z1, R1 is fluoro, R3 isbromo and R2is defined in Table 1.Table A-6 provides 52 compounds A-6.001 to A-6.052 of Formula (I) wherein Z is Z1, R1 is fluoro, R3 ismethyl and R2 is defined in Table 1.Table A-7 provides 52 compounds A-7.001 to A-7.052 of Formula (I) wherein Z is Z1, R1 is hydrogen,R3is chloro and R2is defined in Table 1.Table A-8 provides 52 compounds A-8.001 to A-8.052 of Formula (I) wherein Z is Z1, R1 is hydrogen,R3is fluoro and R2is defined in Table 1.Table A-9 provides 52 compounds A-9.001 to A-9.052 of Formula (I) wherein Z is Z1, R1 is hydrogen,R3is hydrogen and R2is defined in Table 1.Table A-10 provides 52 compounds A-10.001 to A-10.052 of Formula (I) wherein Z is Z1, R1 is hydrogen,R3is cyano and R2is defined in Table 1.Table A-11 provides 52 compounds A-11.001 to A-11.052 of Formula (I) wherein Z is Z1, R1 is hydrogen,R3is bromo and R2is defined in Table 1.Table A-12 provides 52 compounds A-12.001 to A-12.052 of Formula (I) wherein Z is Z1, R1 is hydrogen,R3is methyl and R2is defined in Table 1.Table A-13 provides 52 compounds A-13.001 to A-13.052 of Formula (I) wherein Z is Z1, R1 is chloro,R3is chloro and R2is defined in Table 1.Table A-14 provides 52 compounds A-14.001 to A-14.052 of Formula (I) wherein Z is Z1, R1 is chloro,R3is fluoro and R2is defined in Table 1.Table A-15 provides 52 compounds A-15.001 to A-15.052 of Formula (I) wherein Z is Z1, R1 is chloro,R3is hydrogen and R2is defined in Table 1.Table A-16 provides 52 compounds A-16.001 to A-16.052 of Formula (I) wherein Z is Z1, R1 is chloro,R3is cyano and R2is defined in Table 1. 111607-FF 23Table A-17 provides 52 compounds A-17.001 to A-17.052 of Formula (I) wherein Z is Z1, R1 is chloro,R3is bromo and R2is defined in Table 1.Table A-18 provides 52 compounds A-18.001 to A-18.052 of Formula (I) wherein Z is Z1, R1 is chloro,R3is methyl and R2is defined in Table 1.Table A-19 provides 52 compounds A-19.001 to A-19.052 of Formula (I) wherein Z is Z2, R1 is fluoro,R3is chloro and R2is defined in Table 1.Table A-20 provides 52 compounds A-20.001 to A-20.052 of Formula (I) wherein Z is Z2, R1 is fluoro,R3is fluoro and R2is defined in Table 1.Table A-21 provides 52 compounds A-21.001 to A-21.052 of Formula (I) wherein Z is Z2, R1 is fluoro,R3is hydrogen and R2is defined in Table 1.Table A-22 provides 52 compounds A-22.001 to A-22.052 of Formula (I) wherein Z is Z2, R1 is fluoro,R3is cyano and R2is defined in Table 1.Table A-23 provides 52 compounds A-23.001 to A-23.052 of Formula (I) wherein Z is Z2, R1 is fluoro,R3is bromo and R2is defined in Table 1.Table A-24 provides 52 compounds A-24.001 to A-24.052 of Formula (I) wherein Z is Z2, R1 is fluoro,R3is methyl and R2is defined in Table 1.Table A-25 provides 52 compounds A-25.001 to A-25.052 of Formula (I) wherein Z is Z2, R1 is hydrogen,R3is chloro and R2is defined in Table 1.Table A-26 provides 52 compounds A-26.001 to A-26.052 of Formula (I) wherein Z is Z2, R1 is hydrogen,R3is fluoro and R2is defined in Table 1.Table A-27 provides 52 compounds A-27.001 to A-27.052 of Formula (I) wherein Z is Z2, R1 is hydrogen,R3is hydrogen and R2is defined in Table 1.Table A-28 provides 52 compounds A-28.001 to A-28.052 of Formula (I) wherein Z is Z2, R1 is hydrogen,R3is cyano and R2is defined in Table 1.Table A-29 provides 52 compounds A-29.001 to A-29.052 of Formula (I) wherein Z is Z2, R1 is hydrogen,R3is bromo and R2is defined in Table 1.Table A-30 provides 52 compounds A-30.001 to A-30.052 of Formula (I) wherein Z is Z2, R1 is hydrogen,R3is methyl and R2is defined in Table 1.Table A-31 provides 52 compounds A-31.001 to A-31.052 of Formula (I) wherein Z is Z2, R1 is chloro,R3is chloro and R2is defined in Table 1. 111607-FF 24Table A-32 provides 52 compounds A-32.001 to A-32.052 of Formula (I) wherein Z is Z2, R1 is chloro,R3is fluoro and R2is defined in Table 1.Table A-33 provides 52 compounds A-33.001 to A-33.052 of Formula (I) wherein Z is Z2, R1 is chloro,R3is hydrogen and R2is defined in Table 1.Table A-34 provides 52 compounds A-34.001 to A-34.052 of Formula (I) wherein Z is Z2, R1 is chloro,R3is cyano and R2is defined in Table 1.Table A-35 provides 52 compounds A-35.001 to A-35.052 of Formula (I) wherein Z is Z2, R1 is chloro,R3is bromo and R2is defined in Table 1.Table A-36 provides 52 compounds A-36.001 to A-36.052 of Formula (I) wherein Z is Z2, R1 is chloro,R3is methyl and R2is defined in Table 1. Formulation Examples Wettable powders a) b) c)active ingredient [compound of formula (I)] 25 % 50 % 75 %sodium lignosulfonate 5 % 5 % -sodium lauryl sulfate 3 % - 5 %sodium diisobutylnaphthalenesulfonate - 6 % 10 %phenol polyethylene glycol ether - 2 % -(7-8 mol of ethylene oxide) highly dispersed silicic acid 5 % 10 % 10 % Kaolin 62 % 27 % -The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration. Powders for dry seed treatment a) b) c)active ingredient [compound of formula (I)] 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. Emulsifiable concentrate active ingredient [compound of formula (I)] 10 % 111607-FF 25 octylphenol polyethylene glycol ether 3 %(4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 3 %castor oil polyglycol ether (35 mol of ethylene oxide) 4 %Cyclohexanone 30 %xylene mixture 50 % Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water. Dusts a) b) c)Active ingredient [compound of formula (I)] 5 % 6 % 4 %talcum 95 % - -Kaolin - 94 % -mineral filler - - 96 %Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed. Extruder granules Active ingredient [compound of formula (I)] 15 %sodium lignosulfonate 2 %carboxymethylcellulose 1 %Kaolin 82 %The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air. Coated granules Active ingredient [compound of formula (I)] 8 %polyethylene glycol (mol. wt.200) 3 % Kaolin 89 % The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner. Suspension concentrate active ingredient [compound of formula (I)] 40 %propylene glycol 10 %nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %Sodium lignosulfonate 10 % 111607-FF 26 carboxymethylcellulose 1 %silicone oil (in the form of a 75 % emulsion in water) 1 %Water 32 %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. Flowable concentrate for seed treatment active ingredient [compound of formula (I)] 40 %propylene glycol 5 %copolymer butanol PO / EO 2 %tristyrenephenole with 10-20 moles EO 2 %1,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 %monoazo-pigment calcium salt 5 %Silicone oil (in the form of a 75 % emulsion in water) 0.2 %Water 45.3 %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. Slow Release Capsule Suspension 28 parts of a combination of the compound of formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate / polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1,6-diaminohexane in5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. Theobtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsulediameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in anapparatus suitable for that purpose. EXAMPLES The following non-limiting examples provide specific synthesis methods for representative compoundsof the present invention, as referred to in Table 2 below. Throughout this description, temperatures aregiven in degrees Celsius (°C). List of Abbreviations 111607-FF 27 br d = broad doublet, br s = broad singlet, °C = degrees Celsius, d = doublet, dd = doublet of doublets,DMF = N,N-dimethylformamide, DMSO = dimethyl sulfoxide, EtOAc = ethyl acetate, m = multiplet, MHz= megahertz, q = quartet, qd = quartet of doublets, s = singlet, t = tripletExample 1: Synthesis of 3-(3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-yl)-1,5-dimethyl-6-thioxo-1,3,5-triazinane-2,4-dione (Compound 1)Step 1: Synthesis of 3-chloro-5-fluoro-6-nitro-1H-indazole N-Chlorosuccinimide (1.10 equiv., 0.820 mmol) was added portionwise to a suspension of 5-fluoro-6-nitro-1H-indazole (0.135 g, 0.745 mmol) in acetonitrile (15 mL / g, 2.03 mL). The reaction mixture washeated at 70°C for 1 hour. The reaction was allowed to cool to room temperature. Water was addedthen the mixture was extracted with ethyl acetate three times. The combined organic extracts werewashed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give crude 3-chloro-5-fluoro-6-nitro-1H-indazole (0.171 g, 0.793 mmol.). This was used in the next step with nofurther purification. 1H NMR (400 MHz, CDCl3) δ = 13.38 (br s, 1H), 8.25 (d, 1H), 7.52 (d, 1H)Step 2: Synthesis of 3-chloro-5-fluoro-6-nitro-1-prop-2-ynyl-indazole To a solution of 3-chloro-5-fluoro-6-nitro-1H-indazole (0.170 g, 0.789 mmol) in acetonitrile (15.0 mL / g, 2.55 mL) was added cesium carbonate (1.5 equiv., 1.18 mmol) followed by 3-bromoprop-1-yne (2.50equiv., 1.97 mmol, 0.211 mL). The reaction mixture was stirred at room temperature for 16 hours. Thereaction was quenched by addition of water, extracted with ethyl acetate (x3). The combined organicextracts were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressureto give 0.196g of crude product. The crude product was purified by flash column chromatography elutingwith a gradient of cyclohexane (100%) to cyclohexane / EtOAc (40%) to give 3-chloro-5-fluoro-6-nitro-1-prop-2-ynyl-indazole (0.115 g, 0.454 mmol). 1H NMR (400 MHz, CDCl3) δ = 8.35 (d, 1H), 7.59 (d, 1H),5.21 (d, 2H), 2.56 (t, 1H) Step 3: Synthesis of 3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-amine 111607-FF 28 To a solution of 3-chloro-5-fluoro-6-nitro-1-prop-2-ynyl-indazole (0.115 g, 0.453 mmol) in DMF (5mL / mmol, 2.27 mL) cooled in an ice bath and under an atmosphere of nitrogen was addedtetrahydroxydiboron (4 equiv., 1.81 mmol) followed by 4,4'-bipyridine (0.05 equiv., 0.0227 mmol). (Note:exothermic reaction.) After 30 minutes the reaction was quenched by addition of water, extracted withethyl acetate (x3). The combined organic extracts were washed with brine, dried over MgSO4, filteredand concentrated under reduced pressure to give 0.133 g of crude product containing 3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-amine. This was used with no further purification.1H NMR (400 MHz, CDCl3) δ= 7.21 (d, 1H), 6.74 (d, 1H), 4.99 (d, 2H), 4.12 (br s, 2H), 2.40 (t, 1H)Step 4: Synthesis of phenyl N-(3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-yl)carbamate To a suspension of 3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-amine (0.100 g, 0.447 mmol) and sodium bicarbonate (3.0 equiv., 1.34 mmol) in ethyl acetate (3 mL / mmol, 1.34 mL) and water (1.5 mL / mmol,0.671 mL) was added phenyl chloroformate (1.2 equiv., 0.537 mmol, 0.0680 mL). The reaction mixturewas heated at 40°C for 1 hour. The reaction was quenched by addition of water, extracted with EtOAc(x3). The combined organic extracts were washed with brine, dried over MgSO4, filtered andconcentrated under reduced pressure. The product was purified by flash column chromatography togive phenyl N-(3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-yl)carbamate (0.124g, 0.361 mmol). 1H NMR(400 MHz, CDCl3) δ = 8.40 (d, 1H), 7.50-7.36 (m, 3H), 7.27 (m, 1H), 7.22 (m, 2H), 5.06 (d, 2H), 2.40 (t,1H)

[0002] 111607-FF 29 Step 5: Synthesis of 3-(3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-yl)-1,5-dimethyl-6-thioxo-1,3,5- triazinane-2,4-dione To a solution of phenyl N-(3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-yl)carbamate (0.124 g, 0.361 mmol)in DMF (3 mL, 38.6 mmol, 3 mL) was added sodium acetate (0.5 equiv., 0.180 mmol) followed by phenylN-methyl-N-(methylcarbamothioyl)carbamate (1.1 equiv., 0.397 mmol). The reaction mixture washeated at 60°C for 2.5 hours. The reaction mixture was quenched by addition of water, extracted withethyl acetate (x3). The combined organic extracts were washed with brine, dried over MgSO4, filteredand concentrated under reduced pressure. The crude product was purified by flash columnchromatography eluting with a gradient cyclohexane (100%) to cyclohexane / EtOAc (40%) to give 3-(3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-yl)-1,5-dimethyl-6-thioxo-1,3,5-triazinane-2,4-dione. 1H NMR(400 MHz, CDCl3) δ = 7.60 (d, 1H), 7.53 (d, 1H), 5.13 (d, 2H), 3.81 (s, 6H), 2.48 (t, 1H)Example 2: Synthesis of ethyl 2-[6-(3,5-dimethyl-2,6-dioxo-4-thioxo-1,3,5-triazinan-1-yl)-3,5-difluoro-indazol-1-yl]propanoate (Compound 5)Step 1: Synthesis of 6-bromo-3,5-difluoro-1H-indazole 6-Bromo-5-fluoro-1H-indazole (1.06 g, 4.73 mmol) and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA) (2 equiv., 9.46 mmol, 3.53 g) were stirredin acetonitrile (16 mL) and acetic acid (1.5 ml / g, 1.6 mL) at 80°C for 7 hours. The reaction mixture waspoured onto ice water and extracted with ethyl acetate. The organics were washed with saturatedsodium thiosulfate, water and brine, then dried with MgSO4, filtered and concentrated under vacuum.The crude mixture was purifiied by reverse phase chromatography (C-18 silica gel, 40-70%acetonitrile / water, eluting around 45%) to give 6-bromo-3,5-difluoro-1H-indazole (0.407 g, 1.75 mmol).1H NMR (400 MHz, CDCl3) δ = 9.24 - 9.05 (m, 1H), 7.65 (dd, 1H), 7.40 (d, 1H)Step 2: Synthesis of ethyl 2-(6-bromo-3,5-difluoro-indazol-1-yl)propanoate 111607-FF 30 6-Bromo-3,5-difluoro-1H-indazole (0.400 g, 1.72 mmol, 0.400 g) and potassium carbonate (1.5 equiv.,2.57 mmol, 0.359 g) were stirred in DMF (5 mL / mmol, 8.6 mL) and ethyl 2-bromopropionate (1.2 equiv.,2.06 mmol, 0.377 g) was added. The reaction was stirred at room temperature for 18 hours. The reactionmixture was concentrated under vacuum and purified by flash column chromatography (12 g silica gel,0-30% ethyl acetate / cyclohexane over 12 minutes, eluting around 10%) to give ethyl 2-(6-bromo-3,5-difluoro-indazol-1-yl)propanoate (0.568 g, 1.71 mmol). 1H NMR (400 MHz, CDCl3) δ = 7.58 (dd, 1H),7.37 (d, 1H), 5.08 (qd, 1H), 4.18 (q, 2H), 1.87 (d, 3H), 1.21 (t, 3H) Step 3: Synthesis of ethyl 2-[6-(tert-butoxycarbonylamino)-3,5-difluoro-indazol-1-yl]propanoate Ethyl 2-(6-bromo-3,5-difluoro-indazol-1-yl)propanoate (0.084 g, 0.25 mmol, 0.084 g), tert-butylcarbamate (1.5 equiv., 0.38 mmol, 0.045 g), cesium carbonate (1.5 equiv., 0.38 mmol, 0.12 g) andXPhos Pd G3 (0.1 equiv., 0.025 mmol, 0.022 g) were stirred in toluene (5 mL / mmol, 1.3 mL) at 150°Cunder microwave irradiation for 2 hours. The reaction mixture was concentrated under vacuum andpurified by flash column chromatography (4 g silica gel, 0-50% ethyl acetate / cyclohexane) to give ethyl2-[6-(tert-butoxycarbonylamino)-3,5-difluoro-indazol-1-yl]propanoate (0.088 g, 0.24 mmol). 1H NMR(400 MHz, CDCl3) δ = 8.19 - 8.12 (m, 1H), 7.29 (d, 1H), 6.95 (br d, 1H), 5.14 (qd, 1H), 4.16 (q, 2H), 1.84(d, 3H), 1.55 (s, 9H), 1.20 (t, 3H) Step 4: Synthesis of ethyl 2-(6-amino-3,5-difluoro-indazol-1-yl)propanoate 111607-FF 31 Ethyl 2-[6-(tert-butoxycarbonylamino)-3,5-difluoro-indazol-1-yl]propanoate (0.680 g, 1.84 mmol) wasstirred in dichloromethane (16 mL) and trifluoroacetic acid (3 mL / mmol, 72.1 mmol, 5.5 mL) at roomtemperature for 2 hours. The reaction mixture was concentrated onto celite and purificed by reversephase chromatography (50 g C-18 silica, 40-70% acetonitrile / water, eluting around 50%) to give ethyl2-(6-amino-3,5-difluoro-indazol-1-yl)propanoate (0.404 g, 1.50 mmol). 1H NMR (400 MHz, chloroform)δ = 7.19 (d, 1H), 6.52 (dd, 1H), 4.97 (qd, 1H), 4.16 (q, 2H), 4.11 - 4.02 (m, 2H), 1.81 (d, 3H), 1.19 (t, 3H)Step 5: Synthesis of ethyl 2-[3,5-difluoro-6-(phenoxycarbonylamino)indazol-1-yl]propanoate Ethyl 2-(6-amino-3,5-difluoro-indazol-1-yl)propanoate (0.680 g, 2.53 mmol) and sodium bicarbonate(3 equiv., 7.58 mmol, 0.643 g) were stirred in ethyl acetate (12 mL) and water (4 mL). Phenylchloroformate (1.2 equiv., 3.03 mmol, 0.484 g) was added and the reaction was heated to 40°C for 2hours. The reaction mixture was separated and the organics were concentrated onto celite forpurification by reverse phase chromatography (24 g silica, 0-40% ethyl acetate / cyclohexane, elutingaround 22%) to give ethyl 2-[3,5-difluoro-6-(phenoxycarbonylamino)indazol-1-yl]propanoate (0.615 g,1.58 mmol). 1H NMR (400 MHz, chloroform) δ = 8.21 (br d, 1H), 7.48 - 7.40 (m, 3H), 7.37 (d, 1H), 7.32- 7.27 (m, 1H), 7.25 - 7.19 (m, 2H), 5.09 (dd, 1H), 4.20 - 4.09 (m, 2H), 1.84 (d, 3H), 1.19 (t, 3H)Step 6: Synthesis of ethyl 2-[6-(3,5-dimethyl-2,6-dioxo-4-thioxo-1,3,5-triazinan-1-yl)-3,5-difluoro- indazol-1-yl]propanoate Ethyl 2-[3,5-difluoro-6-(phenoxycarbonylamino)indazol-1-yl]propanoate (0.600 g, 1.54 mmol), phenyl N- methyl-N-(methylcarbamothioyl)carbamate (1.1 equiv., 1.70 mmol, 0.380 g) and sodium acetate(0.5 equiv., 0.771 mmol, 0.0638 g) were stirred in DMF (8 mL) at 60°C under nitrogen for 1 hour. Thereaction mixture was concentrated onto celite for purification by flash column chromatography (24 gsilica, 0-40% ethyl acetate / cyclohexane, eluting around 22%) followed by reverse phase 111607-FF 32chromatography (50 g C-18 silica, 60-100% acetonitrile / water, eluting around 72%) to give ethyl 2-[6-(3,5-dimethyl-2,6-dioxo-4-thioxo-1,3,5-triazinan-1-yl)-3,5-difluoro-indazol-1-yl]propanoate. 1H NMR(400 MHz, chloroform) δ = 7.54 - 7.46 (m, 1H), 7.36 (dd, 1H), 5.10 (qd, 1H), 4.22 - 4.10 (m, 2H), 3.79(s, 6H), 1.86 (d, 3H), 1.17 (t, 3H) Example 3: Synthesis of 3-(3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-yl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione (Compound 6)Step 1: Synthesis of 3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-amine To a stirred solution of 3-chloro-5-fluoro-6-nitro-1-prop-2-ynyl-indazole (600 mg, 2.37 mmol) in ethanol(8 mL) was added iron (528 mg, 9.46 mmol) at room temperature. The reaction mixtutre was heated to80°C. Ammonium chloride (506 mg, 9.46 mmol) in water (2 mL) was added at 80°C. The resultingreaction mixture was stirred at 80°C for 4 hours. The reaction mixture was quenched with water (20 mL)and filterd through a celite bed. The filtrate was basified with saturated NaHCO3 solution, extractedwith EtOAc (2 x 50 mL). The combined organic layers were washed with brine (20 mL), dried overNa2SO4 and concentrated under reduced pressure. The crude residue was purified by chromatography(0 to 40% EtOAc / hexane ). Pure fractions were combined and evaporated under reduced pressure toobtain 3-chloro-5-fluoro-6-nitro-1-prop-2-ynyl-indazole.1H-NMR (400 MHz, DMSO-d6) δ = 7.26 (d, 1H),6.78 (d, 1H), 5.81 (s, 2H), 5.10 (d, 2H), 3.41 (t, 1H)Step 2: Synthesis of 3-(3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-yl)-6-(trifluoromethyl)-1H- pyrimidine-2,4-dione To a stirred solution of 3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-amine (400 mg, 1.79 mmol) in aceticacid (10.0 mL) was added 2-(dimethylamino)-4-(trifluoromethyl)-1,3-oxazin-6-one (447 mg, 2.15 mmol)at room temperature. The resulting reaction mixture was stirred at 80°C for 16 hours. The reactionmixture was quenched with water (50 mL) and extracted with EtOAc (2 x 50 mL). The combined organiclayers were washed with brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude mixture was purified by flash chromatography and eluted with 0-100% of EtOAc in hexanes, 111607-FF 33 pure fractions were concentrated under reduced pressure to obtain 3-(3-chloro-5-fluoro-1-prop-2-ynyl- indazol-6-yl)-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione. Step 3: Synthesis of 3-(3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-yl)-1-methyl-6- (trifluoromethyl)pyrimidine-2,4-dione To a stirred solution of 3-(3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-yl)-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (150 mg, 0.388 mmol) in DMF (10 mL) were added potassium carbonate (161 mg,1.16 mmol) and iodomethane (0.0483 mL, 0.776 mmol) at 0 °C. The resulting reaction mixture wasstirred at room temperature for 16 hours. The reaction mixture was quenched with water (50 mL) andextracted with EtOAc (2 x 50 mL). The combined organic layers were washed with brine (20 mL), driedover Na2SO4 and concentrated under reduced pressure. The crude was purified by flashchromatography and eluted with 0-100% of EtOAc in hexanes, pure fractions were concentrated under reduced pressure to obtain 3-(3-chloro-5-fluoro-1-prop-2-ynyl-indazol-6-yl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione.1H-NMR (400 MHz, DMSO-d6) δ = 7.98 (d, 1H), 7.79 (d, 1H), 6.63(s, 1H), 5.34 (d, 2H), 3.48 (t, 1H), 3.43 (s, 3H)Table 2: 1H NMR Data for selected compounds of the invention.Compound Compound Structure &1H NMR Data No. Name ethyl 2-[3-chloro-6- (3,5-dimethyl-2,6- dioxo-4-thioxo- 1,3,5-triazinan-1- yl)indazol-1- 1 yl]propanoate 1H NMR (400 MHz, CDCl3) δ = 7.82 (d, 1H), 7.36 (s, 1H), 7.11 (d, 1H), 5.23 (q, 1H), 4.17 (q, 2H), 3.8(s, 6H), 1.91 (d, 3H), 1.18 (t, 3H) 111607-FF 34 Compound Compound Structure &1H NMR Data No. Name ethyl 2-[3-chloro-6- (3,5-dimethyl-2,6- dioxo-4-thioxo- 1,3,5-triazinan-1- yl)-5-fluoro-indazol- 2 1-yl]propanoate 1H NMR (400 MHz, CDCl3) δ = 7.53 (d, 1H), 7.42 (d, 1H), 5.21 (q, 1H), 4.17 (q, 2H), 3.80 (s, 6 H), 1.91 (d, 3H), 1.19 (t, 3H) 3-(3-chloro-5- fluoro-1-prop-2- ynyl-indazol-6-yl)- 1,5-dimethyl-6- thioxo-1,3,5- 3 triazinane-2,4-dione 1H NMR (400 MHz, CDCl3) δ = 7.60 (d, 1H), 7.53 (d, 1H), 5.13 (d, 2H), 3.81 (s, 6H), 2.48 (t, 1H) 3-(3-chloro-1-prop- 2-ynyl-indazol-6-yl)- 1,5-dimethyl-6- thioxo-1,3,5- triazinane-2,4-dione 4 1H NMR (400 MHz, DMSO-d6) δ = 7.86 - 7.84 (m, 1H), 7.84 -7.80 (m, 1H), 7.31 (dd, 1H), 5.33 (d, 2H), 3.64 (s, 6H), 3.47 (t, 1H) ethyl 2-[6-(3,5- dimethyl-2,6-dioxo- 4-thioxo-1,3,5- triazinan-1-yl)-3,5- 5 difluoro-indazol-1- yl]propanoate 111607-FF 35 Compound Compound Structure &1H NMR Data No. Name 1H NMR (400 MHz, CDCl3) δ = 7.54 - 7.46 (m, 1H), 7.36 (dd,1H), 5.10 (qd, 1H), 4.22 - 4.10 (m, 2H), 3.79 (s, 6H), 1.86 (d,3H), 1.17 (t, 3H) 3-(3-chloro-5- Cl fluoro-1-prop-2- F ynyl-indazol-6-yl)-1- O N methyl-6- N N (trifluoromethyl)pyri 6 midine-2,4-dione F CH N O F F CH31H-NMR (400 MHz, DMSO-d6) δ = 7.98 (d, 1H), 7.79 (d, 1H), 6.63 (s, 1H), 5.34 (d, 2H), 3.48 (t, 1H), 3.43 (s, 3H)Biological examples Pre-emergence biological efficacySeeds of a variety of test species (Euphorbia heterophylla (EPHHL), Echinochloa crus-galli (ECHCG),Amaranthus palmeri (AMAPA), Setaria faberi (SETFA), Ipomoea hederacea (IPOHE), Lolium perenne(LOLPE), Zea mays (ZEAMX), (Glycine max (GLXMA), and Triticum aestivum (TRZAW)), are sown inTMA soil in pots. After cultivation for one day under controlled conditions in a glasshouse (at 24 °C / 19 °C, day / night; 16 hours light; 50 % humidity), the plants are sprayed with an aqueous spray solution derived from the formulation of the technical active ingredient in a small amount of acetone and a special solvent and emulsifier mixture referred to as IF50 (11.12 % Emulsogen EL360 TM + 44.44 % N- methylpyrrolidone + 44.44 % Dowanol DPM glycol ether), to create a 50 g / L solution which was then diluted using 0.2 % Genapol XO80 as diluent to give the desired final dose of test compound. The testplants are then grown in a glasshouse under controlled conditions in a glasshouse (at 24 °C / 18 °C,day / night; 15 hours light; 40 % humidity) and watered twice daily. After 13 days the test is evaluated for the percentage damage caused to the plant. The biological activities are shown in the following tableson a five-point scale (5 = 81-100 %; 4 = 61-80 %; 3=41-60 %; 2=21-40 %; 1=1-20 %; - = not tested).TABLE B1: Application pre-emergence Cpd. Rate L G A P A E E X A H C A F H P M M W H H T O L A No. (g / ha) P E A X C M O L Z E E A SPIL E Z G R T 1250 5 5 5 5 5 3 - - -2 250 5 5 5 5 4 4 - - -3 125 - - 5 - - - 3 1 3 111607-FF 36 Cpd. Rate L G A H C P A E E X A H H A F W T H PL M M A X A No. (g / ha) P O Z E C M E E SPIO E L L Z R A G T 4125 - - 5 - - - 3 1 2Post-emergence biological efficacySeeds of a variety of test species (Chenopodium album (CHEAL), Amaranthus palmeri (AMAPA),Amaranthus rudis (AMATA), (Ipomoea hederacea (IPOHE), Echinochloa crus-galli (ECHCG), Setariafaberi (SETFA), Digitaria sanguinalis (DIGSA), Lolium perenne (LOLPE), Euphorbia heterophylla(EPHHL), and Eleusine indica (ELEIN)), are sown in standard soil in pots. After cultivation for 14 daysunder controlled conditions in a glasshouse (at 24 °C / 18 °C, day / night; 15 hours light; 40 % humidity), the plants are sprayed with an aqueous spray solution derived from the formulation of the technical active ingredient in a small amount of acetone and a special solvent and emulsifier mixture referred to as IF50 (11.12 % Emulsogen EL360 TM + 44.44 % N-methylpyrrolidone + 44.44 % Dowanol DPM glycol ether), to create a 50 g / L solution which was then diluted using 0.2 % Genapol XO80 as diluent to give the desired final dose of test compound. The test plants are then grown in a glasshouse under controlledconditions in a glasshouse (at 24 °C / 18 °C, day / night; 15 hours light; 40 % humidity) and watered twicedaily. After 13 days the test is evaluated for the percentage damage caused to the plant. The biologicalactivities are shown in the following table on a five-point scale (5 = 81-100 %; 4 = 61-80 %; 3=41-60 %;2=21-40 %; 1=1-20 %; - = not tested).TABLE B2: Application post-emergence L A A LG EAE A Cpd. RateNITPA HPC F SH EAE A LT HHOGIL No. (g / ha) EH POMM CPEID S L E C A E A 1250 5 5 - 5 5 5 5 5 5 42 250 5 5 - 5 5 5 5 5 5 53 125 5 5 5 5 5 5 4 5 - 54 125 5 5 5 3 5 4 2 4 - 15 30 5 5 5 5 4 1 1 1 - 46 30 5 5 5 5 5 5 5 5 - 5

Claims

111607-FF 37 CLAIMS:

1. A compound of Formula (I):wherein Z is Z1or Z2:Z1 Z2; R1is hydrogen or halogen; R2is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2- C6haloalkynyl, C1-C6alkoxyC1-C6alkyl, carboxyC1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkylC2-C6alkynyl, C1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkoxyC1-C6alkylcarbonylC1-C6alkyl, C1-C6alkoxyC1-C6alkoxycarbonylC1-C6alkyl, C1-C6alkoxycarbonylC1-C6alkoxycarbonylC1-C6alkyl, C1- C6alkylcarbonyloxyC1-C6alkyl, C1-C6alkylaminocarbonylC1-C6alkyl, N,N-di(C1-C6alkyl)aminocarbonylC1-C6alkyl, (Ra)(Rb)C=NCO2C1-C3alkyl, N,N-di(C1-C6alkyl)aminooxycarbonylC1-C6alkyl, C1-C6alkoxycarbonylC1-C6haloalkyl, cyanoC1-C6alkyl, C1-C6alkylsulfonylC1-C6alkyl, phenyl, phenylC1-C3alkyl, phenylC2-C6alkenyl, phenylC2-C6alkynyl, phenylcarbonyloxyC1-C3alkyl, heterocyclyl,heterocyclylC1-C3alkyl, wherein each heterocyclyl moiety is a 4-, 5- or 6-membered non-aromaticmonocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S,heteroarylcarbonylC1-C3alkyl, or heteroarylC1-C3alkyl, wherein each heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and wherein the phenyl, heterocyclyl and heteroaryl moieties may be optionally substituted with 1, 2, 3, or 4 groups, which may be the same or different, represented by R4; R3is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2- C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxyC1-C6alkyl, C1-C6alkylcarbonyloxyC1-C6alkyl, C1- C6alkylaminocarbonylC1-C6alkyl, N,N-di(C1-C6alkyl)aminocarbonylC1-C6alkyl, cyanoC1-C6alkyl, C1-C6alkylsulfonylC1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, phenyl, phenylC1-C3alkyl,heterocyclyl, heterocyclylC1-C3alkyl, wherein each heterocyclyl moiety is a 4-, 5- or 6-membered non-111607-FF 38 aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S,heteroaryl, or heteroarylC1-C3alkyl, wherein each heteroaryl moiety is a 5- or 6-membered aromatic ringwhich comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S; R4is halogen, cyano, nitro, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylsulfanyl, C3-C6cycloalkyl, or C1-C6alkoxycarbonyl; andRaand Rbare each independently C1-C6alkyl; or a salt or an N-oxide thereof.

2. The compound according to claim 1, wherein R1 is hydrogen, fluoro, or chloro.

3. The compound according to claim 1 or claim 2, wherein R2 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxyC1-C6alkyl, carboxyC1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkylC2-C4alkynyl, C1- C6alkoxycarbonylC1-C6alkyl, C1-C6alkoxyC1-C4alkylcarbonylC1-C4alkyl, C1-C6alkoxyC1- C6alkoxycarbonylC1-C6alkyl, C1-C6alkoxycarbonylC1-C6alkoxycarbonylC1-C6alkyl, C1- C4alkylcarbonyloxyC1-C4alkyl, C1-C4alkylaminocarbonylC1-C4alkyl, N,N-di(C1-C4alkyl)aminocarbonylC1-C4alkyl, (Ra)(Rb)C=NCO2C1-C3alkyl, N,N-di(C1-C6alkyl)aminooxycarbonylC1-C4alkyl, C1-C6alkoxycarbonylC1-C6haloalkyl, cyanoC1-C6alkyl, C1-C6alkylsulfonylC1-C4alkyl, phenyl, phenylC1-C3alkyl, phenylC2-C4alkenyl, phenylC2-C4alkynyl, phenylcarbonyloxyC1-C3alkyl, heterocyclyl,heterocyclylC1-C3alkyl, wherein each heterocyclyl moiety is a 4-, 5- or 6-membered non-aromaticmonocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S,heteroarylcarbonylC1-C3alkyl, or heteroarylC1-C3alkyl, wherein each heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1, 2, or 3 heteroatoms individually selected from N, O and S, and wherein the phenyl, heterocyclyl and heteroaryl moieties may be optionally substituted with 1, 2, or 3 groups, which may be the same or different, represented by R4.

4. The compound according to any one of claims 1 to 3, wherein R2 is hydrogen, C1-C6alkyl, C1-C4haloalkyl, C2-C5alkenyl, C2-C4haloalkenyl, C2-C6alkynyl, C2-C5haloalkynyl, C1-C6alkoxyC1-C4alkyl, carboxyC1-C4alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C4alkyl, C3-C6cycloalkylC2-C4alkynyl, C1- C6alkoxycarbonylC1-C6alkyl, C1-46alkoxyC1-C4alkylcarbonylC1-C4alkyl, C1-C4alkoxyC1- C4alkoxycarbonylC1-C4alkyl, C1-C6alkoxycarbonylC1-C6alkoxycarbonylC1-C6alkyl, C1- C4alkylcarbonyloxyC1-C3alkyl, C1-C4alkylaminocarbonylC1-C3alkyl, N,N-di(C1-C3alkyl)aminocarbonylC1-C3alkyl, (Ra)(Rb)C=NCO2C1-C3alkyl, N,N-di(C1-C6alkyl)aminooxycarbonylC1-C3alkyl, C1-C4alkoxycarbonylC1-C4haloalkyl, cyanoC1-C4alkyl, C1-C4alkylsulfonylC1-C3alkyl, phenyl, phenylC1-C2alkyl, phenylC2-C3alkenyl, phenylC2-C3alkynyl, phenylcarbonyloxyC1-C2alkyl, heterocyclyl,heterocyclylC1-C2alkyl, wherein each heterocyclyl moiety is a 5- or 6-membered non-aromaticmonocyclic ring comprising 1 or 2 heteroatoms individually selected from N, O and S,heteroarylcarbonylC1-C2alkyl, or heteroarylC1-C2alkyl, wherein each heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S,111607-FF 39 and wherein the phenyl, heterocyclyl and heteroaryl moieties may be optionally substituted with 1 or 2 groups, which may be the same or different, represented by R4.

5. The compound according to any one of claims 1 to 4, wherein R2 is C1-C6alkyl, C1-C4haloalkyl,C2-C5alkenyl, C2-C6alkynyl, C2-C5haloalkynyl, C1-C6alkoxyC1-C4alkyl, carboxyC1-C4alkyl, C3- C6cycloalkyl, C3-C6cycloalkylC1-C4alkyl, C1-C6alkoxycarbonylC1-C6alkyl, C1-C4alkoxyC1- C4alkoxycarbonylC1-C4alkyl, C1-C6alkoxycarbonylC1-C6alkoxycarbonylC1-C6alkyl, (Ra)(Rb)C=NCO2C1-C3alkyl, N,N-di(C1-C6alkyl)aminooxycarbonylC1-C3alkyl, C1-C4alkoxycarbonylC1-C4haloalkyl, cyanoC1-C4alkyl, phenylcarbonyloxyC1-C2alkyl, and wherein each phenyl moiety may be optionally substituted with a single R4group.

6. The compound according to any one of claims 1 to 5, wherein R4 is halogen, cyano, nitro, C1-C3alkyl, or C1-C3alkoxy.

7. The compound according to any one of claims 1 to 6, wherein R3 is hydrogen, halogen, cyano,or C1-C6alkyl.

8. The compound according to any one of claims 1 to 7, wherein R3 is halogen.

9. The compound according to any one of claims 1 to 8, wherein Z is Z1.

10. A herbicidal composition comprising a compound according to any one of the previous claims and an agriculturally acceptable formulation adjuvant.

11. A herbicidal composition according to claim 10, further comprising at least one additionalpesticide.

12. A herbicidal composition according to claim 11, wherein the additional pesticide is a herbicide or herbicide safener.

13. A method of controlling weeds at a locus comprising applying to the locus of a weed controllingamount of a composition according to any one of claims 10 to 12.

14. Use of a compound of Formula (I) according to any one of claims 1 to 9 as a herbicide.

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