MXPA97005015A - 2-substitute phenilpiridines, their procedure debottention and the herbicidal compositions that contain them - Google Patents

Abstract

Substituted I2-phenylpyridines of the following Formula (I): wherein: n = 0.1, R2, R3, R4 = O, OH, SH, NO2, NHS2, CN, COOH, CONH2, halogen, alkyl, haloalkyl alkoxy, haloalkoxy, alkylamino, dialkylamino, alkylthio, haloalkylthio, alkylaminocarbonyl, dialkylaminocarbonyl, R 2 = H, OH, SH, NO 2, NH 2, CN, halogen, alkyl, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkyl sulfonyl, R5 = H, CN, halogen, R6, R8 = H, halogen, R7 = H, OH, NO2, CH, CF3-SO2-O, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, X = oxygen or sulfur; R9, R10 = H, alkyl, m = from 1 to 4, R11 = alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkoxycarbonyl, alkoxycarbonylalkyl-phenyl, thienyl, furanyl, tetrahydrofuranyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl or pyrimidyl, optionally substituted, in which substitution may be resorted to to NO2, CN, halogen, alkyl and alkoxy, R12, R13 = alkoxy, alkylthio, or, together with the carbon atom in common: R14 = H, alkyl, alkenyl, haloalkenyl, alkoxycarbonylalkyl-, benzyl; Z = ethylenic or trimethylenic chain; , eventually replaced, as well as its salts. Application as a herbicide, for the dissection / defoliation of plant

Description

2-SUBSTITUTED PHENILPIRIDINES, THEIR PROCEDURE OF OBTAINING AND THE HERBICIDAL COMPOSITIONS THAT CONTAIN THEM.

Description The present invention relates to novel substituted 2-phenylpyridines of the following Formula I: in which the variables have the following meanings: n = 0, 1; R, R, R independently of each other, represent: hydrogen, halogen, Cj-C ^ alkyl, C1-C4-halogen alkyl, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, nitro, amino, Cj- C4- alkylamino, di- (C 1 -C 4 -alkyl) amino, mercapto, C C 4 -alkylthio, Cj-C 4 -haloalkylthio, cyano, carboxyl, aminocarbonyl, C 1 -C 4 -alkylaminocarbonyl, or di- (Cj-C 4 -alkyl) aminocarbonyl; R = hydrogen, halogen, C j -C-alkyl, C j -C -halogen alkyl, cyano, nitro, amino, hydroxy, C 1 -C 4 -halogen alkoxy, mercapto, C j -C 4 -alkylthio, C 4 -C 4- haloalkyl, C 4 -C 4 alkylsulfinyl, C -Chaloalkylsulfinyl, C j -Calkylsulfonyl, or C j -C 4 -haloalkylsulfonyl; R = hydrogen, cyano or halogen; R6 and R independently from each other, represent hydrogen or halogen; R = represents: hydrogen, nitro, cyano, hydroxy, trifluoromethylsulfonyloxo, halogen, Cj-C4-alkyl, Cj-C4-halogenoalkyl, Cj-C4-alkoxy or Cj-C4-halogen alkoxy; X = hydrogen or sulfur; R, R = independently from each other, represent hydrogen or C C 4 -alkyl; m = represents 1,2, 3 or 4; R1 1 = Cj-Cg-alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl with from one to 5 halogen atoms; C2-C4-alkenyl, C2-C4-halogenoalkenyl with 1 to 3 halogen atoms, (Cj-C4-alkoxy) carbonyl, (C-C4-alkoxy) carbonyl- (C4-C4-alkyl) -, phenyl unsubstituted or substituted one to three times, thienyl, furanyl, tetrahydrofuranyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, thiazolyl, isothiazolyl, pyridyl or pyrimidyl, unsubstituted or substituted from one to three times, in each case substituents are selected from the group consisting of nitro, halogen, CC ^ alkyl and C1-C4-alkoxy; 12 1 'R, R, independently of each other, represent C ^ -alkoxy or Cj-C4-alkylthio, or, together with the carbon atom in common with which they are linked, may represent a carbonyl group, a group: \ C = NO - Rl4 / where R: hydrogen, CC ^ -alkyl C2-C6-alkenyl, C2-C6-haloalkenyl with one to three halogen atoms, (Cj-C4-alkoxy) carbonyl- (C1-C4-) alkyl) - or benzyl, or a heterocycle: Z being an ethylenic or trimethylenic chain, in which, if desired, one to four hydrogen atoms may each be substituted by C1-C4-alkyl or (Cj-C4-alkoxy) carbonyl; as well as the salts usable in agriculture, of the compounds I, insofar as they exist. On the other hand, the present invention also relates to: the use of the compounds I, as herbicides and / or for the dissection and / or defoliation of plants; - means and herbicidal agents for the dissection and / or defoliation of plants, and containing Compounds I as active substances; - procedures to combat the growth or development of unwanted plants, and for the dissection and / or defoliation of plants by Compounds I; and: - processes for the preparation of Compounds I, of herbicidal agents and of agents for the dissection and / or defoliation of plants, by using Compounds I.

In the German Patent Application, above, DE-A 43 23 916, it is revealed that certain 2-phenylpyridines, among others, of the type of compounds I, are compounds effective as herbicides and as desiccants / defoliants. If appropriate substituents are chosen, compounds of the Formula II are, for example: wherein: R represents halogen, cyano, nitro, C 1 -C 4 -alkyl, Cj-C 4 -haloalkyl, C C 4 -alkoxy, C C ^ halogenalkoxy, Cj-C ^ alkylthio or Cj-C4-haloalkylthio; R represents hydrogen, nitro, amino, cyano, hydroxy, mercapto, hydroxycarbonyl, halogen, Cj-C4-alkyl, Cj-C4-haloalkyl, C C4-alkoxy, Cj-C4-halogen alkoxy, C1-C-alkylamino, di- (C1-C4-alkyl) -amino, CC ^ alkylthio, Cj-C ^ haloalkylthio or (C1-C4-alkoxy) carbonyl; R represents hydrogen or halogen; and R represents cyano, nitro, hydroxyl, halogen or trifluoromethyl; Ra represent hydrogen or various organic radicals. However, the herbicidal effect of the known compounds on the harmful plants is not always completely satisfactory. Therefore, the object of the present invention was to develop novel effective herbicidal compositions, with which it would be possible to combat unwanted plants with better results than those achieved up to the present. The object also extends to the preparation of novel effective desiccant / defoliant compositions. By virtue of the foregoing, the substituted 2-phenyl-pyridines of Formula I, as defined above, were discovered. We also discovered herbicidal agents, which contain the compounds I, and which have a very good herbicidal effect. Procedures have also been discovered for the preparation of said agents, and methods for combating the development of unwanted plants, by means of compounds I. On the other hand, it has been discovered that compounds I are also suitable for defoliation and dissection of specific parts. of the plants, specifically taking into account the crop plants such as cotton, potatoes, rapeseed, sunflower, soybean or beans, especially cotton. In this regard, agents for the dissection and / or defoliation of the plants, methods for the preparation of said means, and procedures for the dissection and / or defoliation of the plants, were discovered by the compounds I. The compounds of the Formula I, may contain, depending on the substitution pattern, one or more centers of chirality, in which case they are in the form of mixtures of enantiomers / diastereomers. Both pure enantiomers and diastereomers, as well as mixtures thereof, are objects of the present invention. The substituted 2-phenylpyridines I, can be presented in the form of their salts usable in agriculture; in these cases, the type of salt usually lacks relevance. In general, the salts of those bases and those acid addition salts are used, in which the herbicidal effectiveness is not impaired in comparison with the free compound I. Salts of the alkali metals, in particular, are especially suitable as salts. , the sodium and potassium salts, the alkaline earth metals, preferably the calcium and magnesium salts, the salts of the transition metals, preferably the zinc and iron salts, as well as the ammonium salts, which, if desired, the ammonium ion can carry from one to three substitutes C1-C4-alkyl, hydroxy-C1-C4-alkyl and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium salts and trimethyl- (2-hydroxyethyl) ammonium, and further the phosphonium salts, the sulfonium salts such as preferably the tri (C1-C4-alkyl) sulfonium salts, and the sulfoxonium salts such as preferably the tri- (C1-) salts. C4-alkyl) sulfoxonium. Among the acid addition salts, mention may first be made of the hydrochlorides, hydrobromides, sulfates, nitrates, phosphates, oxalates and the dodecylbenzolsulfonates. The following designations used for the definition of the substituents R to R or of the organic molecules mentioned in the Z chain, namely: alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxy alkoxy, alkylthio, haloalkylthio, alkylamino, dialkyl amino, cycloalkyloxy, cycloalkylamino, diC amino, alkoxycarbonyl, alkoxycarbonyloxy, alkylcarbonyl oxy, halógenoalquilcarboniloxi, cicloal-quilcarboniloxi, alkylaminocarbonyl, dialkylaminocarbonyl, alkylamino carbonyloxy, dialkylaminocarbonylamino, alkylsulfinyl, halo-alkylsulfinyl, alkylsulfonyl, haloalkyl sulfonyl, alkylsulfonyloxy, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylamino and alkynylamino, they represent- the same as the halogen meaning-, generic notions for the individual components of the members of the groups, considered individually. The totality of the carbon chains, ie all the alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, haloalkoxy, halogen alkoxythio, alkenyloxy, alkoxycarbonyl, alkylimino or alkoximino moieties, may be straight or branched chain. The halogenated substituents preferably have one to five halogen atoms, the same or different. By way of example, we have the following meanings: halogen: represents fluorine, chlorine, bromine or iodine; Cj-C4-alkyl, as well as the alkyl part of (Cj-C4-alkoxy) carbonyl- (Cj-C4-alkyl) -, represent: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1- methylpropyl, 2-methylpropyl or 1,1-dimethylethyl; C Cg-alkyl represents: C 1 -C 4 -alkyl, as mentioned above, as also: n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1-ethylpropyl, n -hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-trimethylpropyl, 1,2,2-trimethylpropanyl, 1-ethyl-1- methylpropyl or l-ethyl-2-methylpropyl; Cj-C4-haloalkyl represents: a Cj-C4-alkyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for example: chloromethyl, dichloromethyl, trichloromethyl, fluomethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloro fluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoryl ethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoro-ethyl , 2-chloro-2,2-difluoromethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, penta fluorethyl, 2-fluo ropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3 , 3,3-pentafluor propyl, heptafluofropyl, l- (fluoromethyl) -2-fluorethyl, l- (chloromethyl) -2-chloroethyl, 1- (bromo methyl) -2-bromomethyl, 4-fluorbutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorbutyl; C1-C4-alkoxy, represents: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy; Cj-C4-halogenoalkoxy represents: Cl-C4-alkoxy as mentioned above, which is totally or partially substituted by fluorine, chlorine, bromine and / or iodine, ie, for example: difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, -fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluor ethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2,2,2-tri chloroethoxy, pentafluor ethoxy, 2-fluorohydroxy, 3-fluorohydroxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluor propoxy, 2,3-difluofropoxy, 2,3-dichloro propoxy, 3,3,3-trifluofropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-penta fluorine propoxy, heptafluofropoxy, 1 - ( fluorine methyl) -2-fluorethoxy, 1- (chloromethyl) -2-chloroethoxy, l- (bromomethyl) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluoro butoxy; (Cj-C4-alkoxy) carbonyl, as well as the alkoxycarbonyl part of (C1-C4-alkoxy) carbonyl- (C1-C-alkyl), represents: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n- butoxycarbonyl, 1-methylpropoxyocarbonyl, 2-methylpropoxycarbonyl, or dimethylethoxycarbonyl.

C2-C4-alkylthio, represents: methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio; C 1 -C 4 -halogenalkylthio represents: C 1 -C 4 -alkylthio as mentioned above, partially or completely substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, difluoromethylthio, trifluoromethylthio, chlorodifluor methylthio, bromodifluoromethylthio, 2-fluorethylthio, 2-Chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2 -difluorethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluorethylthio, 2-fluoro-propylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluofropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluorpropylthio, heptafluoropropylthio, 1- (fluomethyl) - 2-fluorethyl, l- (chloromethyl) -2-chloroethylthio, l- (bromomethyl) -2-bromo methylthio, 4-fluorbutylthio, 4-chlorobutylthio, 4-bromobutyl thio or nonafluorbutylthio; C1-C4-alkylsulfinyl, represents: methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulphinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropyl sulfinyl, or 1,1-dimethylethylsulphinyl; CC -halogenoalkylsulfinyl, represents: C 1 -C 4 -alkylsulfinyl as mentioned above, partially or wholly substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, difluoromethyl-sulfinyl, trifluoromethyl-sulfinyl, chlorodifluoromethyl-sulphonyl, bromodifluoromethyl-sulfinyl, 2-fluoro-methyl-sulfinyl, 2-chloroethylsulfonyl, 2-bromoethyl sulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethyl sulfinyl, 2,2,2-trifluoromethyl-sulfinyl, 2,2,2-trichloroethyl-sulfinyl, 2-chloro-2-fluoro-methyl-sulfinyl, 2-chloro -2,2-difluoromethyl sulfinyl, 2,2-dichloro-2-fluoro-methyl-sulfinyl, pentafluoroethyl-sulfinyl, 2-fluoro-propyl-sulfinyl, 3-fluoropropylsulfinyl, 2-chloro-propylsulfinyl, 3-chloropropyl-sulfinyl, 2-bromo propylsulfinyl, 3-bromopropylsulfinyl, 2,2-difluoropropyl sulfinyl, 2,3-difluoropylsulfinyl, 2,3-dichloropropyl sulfinyl, 3,3,3-trifluoropylsulfinyl, 3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropyl sulfinyl, heptafluopropylsulfinyl, 1- (fluomethyl) -2-fluorethyl sulfinyl, 1- (chloromethyl) ) -2-chloroethylsulfinyl, 1- (bromo methyl) -2-bromomethylsulfinyl, 4-fluorobutyl sulfinyl, 4-bromobutylsulfinyl or nonafluorbutylsulfinyl; C -C -alkylsulfonyl, represents: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropyl sulfonyl, or 1,1-dimethylethylsulfonyl; Cj-C4 -halogenoalkylsulfonyl, represents: Cj-C4-alkylsulfonyl as mentioned above, substituted partially or wholly by fluorine, chlorine, bromine and / or iodine, ie, for example, difluoromethyl sulfonyl, trifluoromethylsulphonyl, chlorodifluoromethyl-sulfonyl, bromodifluoromethyl-sulfonyl, 2- fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethyl sulfonyl, 2-iodo-ethylsulfonyl, 2,2-difluoroethylsulphonyl, 2,2,2-trifluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, 2-chloro-2-fluorethylsulfonyl, 2 -chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, pentafluorosulfonyl, 2-fluoro-phenylsulfonyl, 3-fluoropropyl sulfonyl, 2-chloro propylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropyl sulfonyl, 3-bromopropylsulfonyl , 2,2-difluoropropyl sulfonyl, 2,3-difluopropylsulfonyl, 2,3-dichloro propyl sulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropyl sulfonyl, 2,2,3, 3,3- pentafluor propyl sulfonyl, heptafluor propyl sulfonyl, 1- (fluomethyl) -2-fluorethylsulfonyl, 1 - (chloromethyl) -2-chloroethylsulfonyl, 1- (bromomethyl) -2-bromomethyl sulfonyl, 4-fluorbutylsulfonyl, 4-bromobutylsulfonyl or nona fluorbutylsulfonyl; Cj-C ^ alkylamino, as also the alkylamino part of (Cj-C4-alkylamino) carbonyl, represents: methylamino, ethylamino, n-propyl amino, 1-methyl ethyl amino, n-butylamino, 1-methyl-propylamino, 2- methyl propyl amino, or 1,1-dimethylethylamino; Di- (Cj-C4-alkyl) amino, as also the dialkylamino part of di- (C1-C4-alkyl) aminocarbonyl, represents for example: N, N-dimethylamino, N, N-diethylamino, N, N-diisopropylamino, N, N-dibutylamino, N, N-di- (1-methyl-propyl) amino, N, N-di- (2-methylpropyl) amino, N, N-di- (1, 1-dimethylethyl) amino, N -ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N- (l-methyl ethyl) amino, N-butyl-N-methyl amino, N-methyl-N- (l-methyl propyl) amino, N-methyl-N- (2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N-methylamino, N-ethyl-N-propylamino, N-ethyl-N- (1-methylethyl) amino, N-butyl-N-ethylamino, N-ethyl-N- (1-methylpropyl) amino, N-ethyl-N- (2-methylpropyl) amino, N-ethyl-N- (1, 1-dimethylethyl) -amino, N- (l -methyl ethyl) -N-propylamino, N-butyl-N-propylamino, N- (l -methylpropyl) -N-propylamino, N- (2-methylpropyl) -N-propylamino, N - (1,1-dimethylethyl) -N-propyl amino, N-butyl-N- (1-methylethyl) amino, N- (1-methylethyl) -N- (1-methyl-ropil) amino, N- (1) -methyl ethyl) -N- (2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N- (methyl ethylamino), N-butyl-N-methyl p ropil) amino, N-butyl-N- (2-methyl propyl) amino, N-butyl-N- (1, 1-dimethylethyl) amino, N- (1-methylpropyl) -N- (2-methylpropyl) amino , N- (1, 1-dimethylethyl) -N- (1-methylpropyl) amino, or N- (1, 1-dimethylethyl) -N- (2-methylpropyl amino); C -C ^ -cycloalkyl represents: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; C2-C4-alkenyl, represents: ethynyl, prop-1-en-1-yl, prop-2-en-l-yl, 1-methylethenyl, n-buthen-1-yl, n-buthen-2-yl, n-butylene-3-yl, 1-methyl-prop-1-en-1-yl, or 2-methyl-prop-1-en-1-yl; C2-C ^ -alkenyl, represents: C2-C4-alkyl, as mentioned above, as also for example: n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n- penten-4-yl, 1-methyl-but-l-en-l-yl, 2-methyl-but-l-en-l-yl, 3-methyl-but-l-en-l-yl, l- methyl-but-2-en-l-yl, 2-methyl-but-2-en-l-yl, 3-methyl-but-2-en-l-yl, l-methyl-but-3-en- l-yl, 2-methyl-but-3-en-l-yl, 3-methyl-but-3-en-l-yl, l, l-dimethyl-pro? -2-en-l-yl, 1 , 2-dimethyl-pro? -l-en-l-yl, 1,2-dimethyl-prop-2-en-l-yl, 1-ethyl-prop-l-en-l-yl, l-ethyl- prop-2-en-l-yl, n-hex-l-en-1-yl, n-hex-2-en-l-yl, n-hex-3-en-l-yl, n-hex- 4-en-l-yl, n-hex-5-en-l-yl, 1-methyl-pent-l-en-l-yl, 2-methyl-pent-l-yl, 3-methyl-pent- l-en-l-yl, 4-methyl-pent-1-en-l-yl, l-methyl-pent-2-en-l-yl, 2-methyl-pent-2-en-l-yl, 3-methyl-pent-2-en-l-yl, 4-methyl-pent-2-en-l-yl, l-methyl-pent-3-en-l-yl, 2-methyl-pent-3 en-l-yl, 3-methyl-pent-3-en-l-yl, 4-methyl-pent-3-en-l-yl, 1-methyl-pent-4-en-l-yl, 2- methyl-pent-4-en-l-yl, 3-methyl-pent-4-en-l-yl, 4-methyl-pent-4-en-l-ii or, 1, 1-dimethyl-but-2-en-1-yl, 1, 1-dimethyl-but-3-en-1-yl, 1,2-dimethyl-but-1-en-1-yl, 1, 2-dimethyl-but-2-en-1-yl, 1,2-dimethyl-but-3-en-1-yl, 1,3-dimethyl-but-1-en-1-yl, 1, 3-dimethyl-but-2-en-1-yl, 1,3-dimethyl-but-3-en-1-yl, 2,2-dimethyl-but-3-en-l-yl, 2,3- dimethyl-but-l-en-l-yl, 2,3-dimethyl-but-2-en-l-yl, 2,3-dimethyl-but-3-en-l-yl, 3,3-dimethyl- but-l-en-l-yl, 3,3-dimethyl-but-2-en-l-yl, 1-ethylbut-1-en-1-yl, l-ethyl-but-2-en-l- ilo, l-ethyl-but-3-en-l-yl, 2-ethyl-but-l-en-l-yl, 2-ethyl-but-2-en-l-yl, 2-ethyl-but- 3-en-l-yl, 1,1,2-trimethyl-pro-2-en-1-yl, 1-ethyl-1-methyl-prop-2-en-1-yl, 1-ethyl-2- methyl-prop-1-en-1-yl or l-ethyl-2-methyl-prop-2-en-l-yl; C -C4-halogenoalkenyl, represents: C-C4-alkenyl, as mentioned above, partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie for example: 2-chloro-allyl, 3-chloro-allyl or 3,3- dichloroallyl; C2-C6-halogenoalkenyl, represents: C2-Cg-alkenyl, as mentioned above, partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie for example: 1-chlorovinyl, 2-chlorovinyl, 2.2- dichlorovinyl, 1,2,3-trichlorovinyl, 2-chloro-allyl, 3-chloro-allyl or 3,3-dichloro-allyl. The phenyl ring and the heterocyclic rings in the definition of R, are preferably unsubstituted, or bear a halogen, methyl or methoxy substituent. As for the application of the compounds of Formula I, according to the present invention, as variables herbicides and / or as effective substances as desiccants / defoliants, the variables preferably have the following meanings, which variables can be considered individually or combined with each other: n is zero; R, R, R independently from each other, are hydrogen or halogen; R is halogen or Cj-C4-haloalkyl, with 1 to 5 halogen atoms; R is hydrogen or halogen, especially fluorine; R, R are hydrogen; R is cyano or halogen, especially cyano or chloro; X is oxygen; R, R independently from each other, are hydrogen or Cj-C4-alkyl; m is zero or two; R is Cj-C ^ -alkyl or C3-C6-cycloalkyl; R 19 and R 11"J" together with the carbon atom to which they are linked represent the carbonyl group.The compounds set forth in the following Table 1 are especially preferred (* I with n = zero, R1, R3, R6, R8 and R10 = hydrogen, R2 = CF3, R = chlorine, R1 = methyl, R and R together with the carbon atom = carbonyl): Table 1: On the other hand, the following substituted 2-phenylpyridines of the Formula I are especially preferred: compounds Ib.01-Ib.32, which differ from the corresponding compounds Ia.01-Ia.32, only in the fact that R represents ethyl: - the compounds Ic.01-Ic.32, which differ from the corresponding compounds Ia.01-Ia.32, only in the fact that R represents n-propyl: - the compounds Id.01-Id.32, which differ from the corresponding compounds Ia.01-Ia.32, only in the fact that R represents isopropyl: the compounds Ie.01-Ie.32, which differ from the corresponding compounds Ia.01-Ia.32, only in the fact that R represents n-butyl: - compounds If.01-If.32, which differ from the corresponding compounds Ia.01-Ia.32, only in the fact that R represents 2-methylpropyl: - the compounds Ig.01-Ig.32, which differ from the corresponding compounds Ia.01-Ia.32, only in the fact that R represents tert-butyl: - the compounds Ih.01-Ih.32, which differ from the corresponding compounds Ia.01-Ia.32, only in the fact that R represents cyclopropyl: - the compounds Ii.01-Ii.32, which differ from the corresponding compounds Ia.01-Ia.32, only in the fact that R represents methoxycarbonylmethyl: - the compounds Ik.01-Ik.32, which differ from the corresponding compounds Ia.01-Ia.32, only in the fact that R represents ethoxycarbonylmethyl: On the other hand, the following substituted 2-phenylpiperids of the formula II are particularly preferred (* I with n = 0; R1, R3, R6, R8 and R10 = hydrogen; R2 = CF3; R4 = chlorine; m = 1;; R1 1 = methyl; R12, R13 = methoxy): Table 2 Finally, the following substituted 2-phenylpyridines I are also especially preferred: - the compounds Im.01-Im.16, which differ from the corresponding compounds 11.16-11.16, only in the fact that R12 and R represent ethoxy: - the compounds In.01-In.16, which differ from the corresponding compounds 11.01-11.16, only in the fact that R and R, together with the carbon atom in common to which they are linked, form a ring of 1 , 3-dioxolane: - the compounds Io.01-Io.16, which differ from the corresponding compounds 11.01-11.16, only in the fact that R and R, together with the carbon atom in common with which they are linked, form a ring of 1,3-dioxane: - the compounds Ip.Ol-Ip.16, which differ from the corresponding compounds 11.01-11.16, only in the fact that R and R, together with the carbon atom in common to which they are linked, form a ring of 1 , 3-dithiol: - the compounds Iq.Ol-Iq.16, which differ from the corresponding compounds 11.01-11.16, only in the fact that R and R, together with the carbon atom in common with which they are linked, form a ring of 1,3-dithian: - the compounds Ir.Ol-Ir.16, which differ from the corresponding compounds 11.01-11.16, only in the fact that R and R, together with the carbon atom in common to which they are linked, form a group: - the compounds Is.01-Is.16, which differ from the corresponding compounds 11.01-11.16, only in the fact that R, together with the carbon atom in common with which they are linked, form a group: ; N OCH3) - the compounds It.01-It.16, which differ from the corresponding compounds 11.01-11.16, only in the fact that R and R, together with the carbon atom in common to which they are linked, form a group: V C = N OC2H5 / The substituted 2-phenylpyridines of Formula I can be obtained in various ways, for example by following one of the following procedures: Procedure A; Alkylation of 3-pyridylphenols or 3-pyridylthiophenols, III, with IV alkylating agents, in the presence of a base: III IV L represents chloro, bromo, iodo, methylsulphonyloxy, trifluoromethyl-sulphonyloxy, phenylsulphonyloxy or p-tolylsulphonyloxy. In general, it is worked in a solvent or diluent, inert, preferably aprotic, therefore, for example: N, N-dimethylformamide, dimethylsulfoxide, acetone, M-methylpyrrolidone, acetonitrile or in an ether such as diethyl ether, tetrahydrofuran or 1, 4-dioxane. As usable bases, for example, alkali metal carbonates and hydrogencarbonates, such as sodium hydrogencarbonate, potassium hydrogen carbonate, sodium carbonate and potassium carbonate, alkali metal alcoholates, such as methanolate, can be used. sodium and tert. potassium butanolate, alkali metal hydroxides such as sodium hydroxide, and alkali metal hydrides such as sodium hydride. Other indications can be found to carry out such alkylation reactions, in for example the following bibliographical references: - C.D. Hurd and P. Perletz. J. Am. Chem. Soc, 68, 38 (1946); - W.M. Best and D. Wege, Aust. J. Chem. 39, 647 (1986); - D. Salunkhe and Other (s), Acta Chim. Hung. 124, 411 (1987); - D.D. Weller and Other (s), J. Org. Chem. 48, 3061 (1983); - J.E. Banfield and Other (s), J. Chem. Soc, 4791 (1956); - . Kukolja and Other (s), J. Med. Chem. 28, 18860 (1985); - K. Goerlitzer and Other (s), Arch. Pharm. 313, 27 (1980); - A. Shafiee and Other (s), J. Het. Chem. 19, 1305 (1982); - E. Campaigne and S. Kim Chung, J. Het. Chem. 20, 1697 (1983); - S. Apparao and R.R. Schmidt, Synthesis 1987, 896; Method B: Reaction of the substituted 2-phenylpyridines I, in which R and R 3 together with the carbon atom in common, to which they are linked, represent the carbonyl group, or with hydroxylamine, in which case the product of the process may then be rented, either with an alcoxyamine H2N-0-R: Dßfinition von L siehe Vßrfahrßn A. For the definition of L, see Procedure A. The conditions for the reaction procedure of said reactions of ketones with hydroxylamine (drvs), can be consulted in for example the following bibliographical references: - N Bodor and Other (s), J. Med. Chem. 31, 100 (1988); - N. Latif and Other (s), Indian J. Chem. B19, No. 4, 301-304 (1980); - M. Watanabe and Other (s), Chem. And Pharm. Bull. 32, 3551 (1984); - P.H.H. Hermkens and Other (s), Tetrahedron 46, 833 (1990); - E.V. Dehmlov and Other (s), Chem. Ber. 119, 2956 (1986); - R. Píate y Otro (s), J. Chem. Soc, Perkin Trans. 1, 2478-2480 (1987); - Y. Tsuda and Other (s), Heterocycles 27, 63 (1988); - J. Koyama and Other (s), Heterocycles 29, 1649 (1989). Procedure C: Reaction of the substituted 2-phenylpyridines I, in which R and R1 together with the carbon atom in common, to which they are linked, represent the carbonyl group, in the presence of an acid, either with divalent alcohols or thioalcohols be with alcohols or monovalent thioalcohols, or with ortho (thio) esters. If desired, the process products I, with R, R = alkoxy or alkoxythio, can be ketalized in the presence of an acid: Other indications can be found to carry out such ketal formation reactions, in for example the following bibliographical references: - D.J. Collins and J.J. Hobbs Chem. Ind., 1063 (1964); - CE. Ballov, Biochem. Prep. 45 (1960); - C.L. Stevens and A.E. Sherr, J. Org. Chem. 17, 1228 (1952); - J.L. Reymond and P. Vogel, J. Chem. Sioc. Commun. 16, 1070 (1990); -. C. Nicolaov and Other (s), Angew. Chem. Int. Ed. 30, 299 (1991); - V. Rosnati and Other (s), Gazz. Chim. Ital. 94, 767-1964); - W.M. Best and D. Wege, Aust. J. Chem. 39, 647 (1986); - K. Kido and Other (s), J. Chem. Soc.Chem. Commun. 8"590 (1986); - M.T.Barros and Other (s), Tetrahedron 44, 2283 (1988); - L.L. Melhado and J.L. Brodsky, J. Org. Chem. 53, 3852 (1988). Procedure D; Oxidation of the substituted 2-phenylpyridines of Formula I, wherein n means zero, in a manner known per se. { see for example Albini and S. Pietra, Heterocyclic N-Oxides, CRC-Press Inc., Boca Raton, USA. 1991; H.S. Mosher and Other (s), Org. Synth Coll. Vol. IV 1963, 828; E.C. Taylor and Other (s), Org. Synth Coll. Vol. IV 1963, 704; T.W.Bell and Other (s), Org. Synth 69, 226 (1990)} : l (n = 0) Oxidation > I (n = l) Among the usual oxidation agents for the oxidation of the phenyl ring are, for example, peracetic acid, pertrifluoroacetic acid, perbenzoic acid, m-perchlorobenzoic acid, monopermaleinic acid, magnesium monoperftalate, sodium perborate, Oxone. MR (containing peroxodisulfate), perwolframic acid and hydrogen peroxide. As a suitable inert solvent, we have for example water, sulfuric acid, carboxylic acids such as acetic acid and trifluoroacetic acid, as well as halogenated hydrocarbons such as dichloromethane and chloroform. Oxidation is normally carried out at a temperature of 0 ° C at the boiling temperature of the reaction mixture. The oxidation agent is usually applied in an amount at least equimolar, based on the starting composition. In general, an excess of the oxidation agent has proved to be particularly advantageous.

Unless otherwise indicated, it is desirable that all the procedures described above be undertaken at atmospheric pressure or under the proper pressure of the reactive mixture of the case. In general, the final part of the preparation of the reactive mixture is carried out according to methods known per se, for example by removing the solvent, distributing the residue in a mixture of water and a suitable organic solvent, and incorporating the phase organic in the product. The starting compounds indicated for the individual processes are either known or can be obtained in a manner known per se, for example according to some of the methods described. The substituted 2-phenylpyridines of Formula I may contain one or several chiral centers, so they usually occur in the form of enantiomeric or diastereomeric mixtures, which mixtures may be optionally separated into their predominantly pure isomers following the usual methods for this, for example by its crystallization or chromatography on an optically active adsorbent. The pure optically active isomers can also be prepared, for example from their corresponding optically active starting materials. If desired, the substituted 2-phenylpyridines I with the CH-acid substituents can be converted in a known manner into their salts, preferably into their alkali metal salts. Usually, the salts of I, whose metal ion is not an alkali metal ion, can be prepared by converting the corresponding alkali metal salt, as well as its ammonium, phosphonium, sulfonium, and sulfoxonium salts, by means of ammonia or Phosphonium, sulfonium or sulfoxonium hydroxides. On the other hand, those I compounds that carry an amino group in terminal position, they can form acid addition salts. In general terms, the salts of those acids which do not negatively influence the herbicidal or desiccant / defolianting effect of I are suitable, that is to say, for example, the hydrochlorides and hydrobromides, sulfates, nitrates, phosphates, oxalates or docecylbenzenesulfonates. The compounds I, as well as their salts usable in agriculture, both in the form of mixtures of isomers and in the form of pure isomers, are suitable as herbicides. The herbicidal agents containing the compound I, serve very well to combat the development of plants in non-growing areas, especially if high amounts of the agent are applied. In crops such as wheat, rice, corn, soybean and cotton, they act against weeds and harmful grasses, without inflicting significant damage to the crop plants. This effect occurs especially if small amounts are applied. Depending on the method of application of each case, Compounds I, or the herbicidal agents that contain them, can also be used in another quantity of crop plants, to combat unwanted plants. Among said crop plants are, for example: Allium cepa, Ananas comosus, Arachis hypogaea, Aspa-ragus officinalis, Beta vulgaris spp. altissima, Beta vulgaris spp. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus lemon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynoson dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herba-ceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usita tissimum, Lycopersicon lycopersicum, Malus spp., Manihot esculenta, Medicago sativa, Musa spp., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lu-natus, Phaseolus vulgaris, Picea abies, Pinus spp., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Sécale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, and Zea mays. It is also possible to apply compounds I in those crops which, thanks to their selective reproduction and / or genetic technology methods, have acquired a certain tolerance against the effect of herbicides. On the other hand, the substituted 2-phenylpyridines I are also suitable for the dissection and / or defoliation of the plants. As dissecans, they are especially suitable for the dissection of aerial parts of crop plants such as potatoes, rapeseed, sunflower and soybeans. This facilitates a fully mechanized harvesting or harvesting of said important crop plants. In addition, it is of economic interest the possibility of alleviating the task of harvesting or harvesting, thanks to the concentration in time, wilt and fall, or reduction of the fixation to the tree, in the case of citrus fruits, of olives (olives) or other fruit species of stone, core or shell type. This same mechanism, that is to say, the stimulation of the configuration of a tissue of separation between the parts of the fruits, or of the leaves or shoots of the plants, is also essential for a well-controlled defoliation of the useful plants, especially cotton. On the other hand, the shortening of the time interval in which the individual cotton plants reach maturity leads to a better quality of the fibers after harvesting or harvesting. The compounds I, or the herbicidal agents containing them, can be applied, for example, in the form of directly sprayable aqueous solutions., powders, suspensions, and also in the form of high-percentage aqueous or oily suspensions or dispersions, in the form of emulsions, oily dispersions, pastes, dusts, sowing agents or granules, by sing, fogging, dusting, seeding or pouring . The forms of application depend on the intended purpose; in all cases, they must guarantee the finest possible distribution of the active substances according to the present invention. The following are essentially taken into account as inert auxiliary materials: fractions of mineral oils with a medium to high boiling point, such as kerosene or diesel oil, as well as coal tar oils and petroleum oils; plant or animal origin, the aliphatic, cyclic and aromatic hydrocarbons, for example, the paraffins, the tetrahydronaphthaline, the alkylated naphthalenes or the derivatives thereof, the alkylated benzoles and their derivatives, the alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents, such as for example amines such as N-methylpyrrolidone, or water. Aqueous application forms can be prepared from concentrated emulsions, suspensions, pastes, wettable powders or granules dispersible in water, by the addition of water. For the preparation of emulsions, pastes or oily dispersions, it is possible to dissolve the substrates as such, in an oil or in a solvent, or to homogenize them by means of wetting, adhesion or emulsification agents, in water. It is also possible to prepare concentrates from the active substances, wetting, dispersing or emulsifying agents, and optionally solvents or oils, which concentrates are apt to be diluted or diluted with water. Surface-active materials (adjuvants) are alkali metal, alkaline earth metal salts, ammonium salts, aromatic sulfonic acids, for example lignin-, phenol-, naphthalene- and dibutylnaphthalene sulphonic acids, as well as fatty acids, alkyl- and alkylaryl sulfonates, alkyl sulfonates, lauryl ether and fatty alcohols, as well as the salts of sulfated hexa-, hepta- and octodecanoles as well as glycol-ether alcohols fatty substances, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalene sulphonic acids with phenol and formaldehyde, polyoxy ethylene-octylphenol ether, isooctyl-, octyl- or nonylphenol ethoxylates, alkylphenyl-, tributylphenylpolyglycol ether, alkylaryl ether polyols, isotridecyl alcohol, fatty alcohol ethylene-oxides condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether, sorbitol ester, lignin sulphite lyes or methyl cellulose. The dusting, seeding and spraying agents can be prepared by mixing or co-grinding the active substance with a material-carrier or solid support-material. The granulates, for example the wrapping, impregnation and homogeneous granulates, can be prepared by linking the active substance with the material-vehicle or solid-support material. As material-carrier or material-support, solid, we have the mineral lands such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus alba (a kind of kaolin), loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers or fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark flour, wood and walnut shells, cellulose powders, or other solid materials-vehicles. The concentrations of the active substances I / I 'in ready-to-apply preparations can be varied in a very wide range. In general, the formulations contain from 0.001 to 98% by weight, preferably from 0.01 to 95 percent by weight, of the active substance. Therefore, the active substances are applied with a purity of 90 percent to 100 percent, preferably from 95 percent to 100 percent (measured by the NMR spectrum). The following formulation examples clarify the obtaining of said preparations: I.- 20 parts by weight, of the compound No. Ia.09 are dissolved in a mixture consisting of 80 parts by weight, of alkylated benzene, 10 parts by weight, of the product from the addition of 8 to 10 mol of ethylene oxide with 1 mol of N-monoethanolamide of oleic acid, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the product of the addition of 40 mol of ethylene oxide with 1 mol of Castor oil. By pouring and fine distribution of the solution in 100,000 parts by weight of water, an aqueous dispersion containing 0.02 weight percent of the active substance is obtained. II.- 20 parts by weight, of the compound No. Ih.09 are dissolved in a mixture consisting of 40 parts by weight, of cyclohexanone, 30 parts by weight, of isobutanol, 20 parts by weight, of the product of the addition of ethylene oxide with 1 mole of isooctylphenol, and 10 parts by weight of the product of the addition of 40 mole of ethylene oxide with 1 mole of castor oil. By pouring and fine distribution of the solution in 100,000 parts by weight of water, an aqueous dispersion containing 0.02 weight percent of the active substance is obtained.

III.- 20 parts by weight of the active substance No.Ia.09 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight, of a fraction of mineral oil having a boiling point of 210 to 280 ° C, and 10 parts by weight, of the product of the addition of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring and fine distribution of the solution in 100,000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of the active substance is obtained. IV.- 20 parts by weight, of the active substance No.Ih.09 are well mixed with 3 parts by weight, of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid consisting of a sulphite lye and 60 parts by weight of silicic acid gel in powder form, and ground in a hammer mill. By spreading and thinly distributing the solution in 20,000 parts by weight of water, a sprayable "broth" containing 0.1% by weight of the active substance is obtained. V. - 3 parts by weight, of the active substance No.Ia.09 are mixed with 97 parts by weight, of finely divided kaolin. In this way, a dusting agent containing 3% by weight of the active substance is obtained. VI.- 20 parts by weight, of the active substance No.Ih.09 are intimately mixed with 2 parts by weight, of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight, of polyglycol ether of fatty alcohols, 2 parts by weight, of sodium salt of a phenol-urea-formaldehyde condensate, and 68 parts by weight of a paraffinic mineral oil. A stable oil dispersion is obtained. VIL- 1 part by weight, of compound Ia.09 is dissolved in a solution consisting of 70 parts by weight, of cyclohexanone, 20 parts by weight, of ethoxylated isooctyl phenol and 10 parts by weight of ethoxylated castor oil. A concentrated, stable emulsion is obtained. VIII.- 1 part by weight, of the compound Ih.09 is dissolved in a solution consisting of 80 parts by weight, of cyclohexanone, and 20 parts by weight, of Emulphor EL (ethoxylated castor oil (castor oil)). A concentrated, stable emulsion is obtained. The application of the active substances I, or of the herbicidal agents, can be carried out in a pre-emergency or post-emergency treatment.

If the active substances are less tolerable for certain crop plants, it is possible to resort to dissemination techniques whereby the herbicidal agents are sprayed by spraying or watering devices in such a way that as far as possible the herbicidal agents do not enter contact with the leaves of the susceptible crop plants, while the active substances if they come in contact with the leaves of the unwanted plants growing below, or with the uncoated soil (post-directed, lay-by). The amounts to be applied of the active substance I, depend on the objective of the struggle, the season or season of the year, the target plants and the state or stage of their development; it varies between 0.001 to 3.0, preferably 0.01 to 1 kg of active substance per hectare. To broaden the spectrum of effectiveness and in order to achieve synergistic effects, it is possible to mix the substituted 2-pheny pyridines, I, with numerous representatives of other groups of active substances such as herbicides or growth regulators, and apply them together.

For example, 1,4-thiadiazole, 1,3,4-thiadiazole, amides, aminophosphoric acids and their derivatives, aminotriazoles, aniidos, aryloxy acids, can be used as co-components of the mixture. lacryl heteroaryloxy and its derivatives, benzoic acids and their derivatives, benzothiadiadiazinone, 2- (hetaroyl / aroyl) -l, 3-cyclohexanedione, heteroaryl-aryl-ketone, benzisoxazolinone, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acids and their derivatives, chloroacetanilide, cyclohexane-l, 3-dione derivatives, diazines, dichloropropionic acids and their derivatives, dihydrobenzofurans, dihydrofuran-3-one, dinitroaniline, dinitrophenols, diphenyl ether, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazo linone, N-phenyl- 3,4,5,6-tetrahydrophthalimide, oxadiazole, phenols, esters of aryloxyphenoxypropionic acids, phenylacetic acids and their derivatives, 2-phenylpropionic acids and their derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acids and their derivatives, pyrimidylether, sulfonamide, sulfonylureas , triazinones, triazolcarbo xamides and uracils. On the other hand, it may be useful to apply the compounds I, alone or in combination with other herbicides, and also in conjunction with other crop protection agents, for example, with agents for controlling pests, fungi and / or phytopathogenic bacteria. It is also interesting the possibility of mixing with solutions of mineral salts, applied in order to counteract or compensate for deficiencies in the nutrition of plants, and the lack of certain (oligo) vestigial elements. It is also possible to add oils and oil concentrates that are not phytotoxic. Preparation Example: Example 1 3-chloro-2-f4-cyano-3- (2-oxopropoxy) phenyl) -5-trifluoromethyl-pyridine (No. Ia.09 15 g of 3-chloro-2- (4-cyano) 3-hydroxyphenyl) -5-trifluor methylpyridine, 1.0 g of chloroacetone, 1.5 g of potassium carbonate, 0.8 g of sodium chloride and 200 ml of acetone were heated for 8 hours at room temperature. After the reaction mixture was recovered, the residue was stirred in 20 ml of water, the insoluble part was separated and washed well with water, then the crude product was stirred together with n-hexane and with ether. After drying in a vacuum drying cabinet, 0.4 g of white crystals with a melting point of 146 - 147 ° C was finally obtained Yield: 22% Preliminary Stage Alpha; 3-Chloro-2- (4-cyano-3-methoxyphenyl) -5-trifluoromethyl-pyridine To a solution of 49.0 g of 3-chloro-2- (4-cyano-3-nitrophenyl) -5-trifluoromethylpyridin ( disclosed in DE-A 43 23 916) in 500 ml of water-free methanol, 31 ml of a 30% by weight solution of sodium methylate in methanol were added. After 6 hours of heating at reflux temperature, the reactive mixture was left to stand for 16 hours at a temperature of 28 ° C, after which the crystals which had been separated were separated, washed with a little methanol and then dried. finally they are dried in a vacuum drying cabinet. Yield: 33.3 g (71% white crystals with a melting point of 135 - 137 ° C.) Preliminary Step Beta: 3-chloro-2- (4-cyano-3-hydroxyphenyl) -5-trifluoromethyl-pyridine 5 , 0 g of 3-chloro-2- (4-cyano-3-methoxyphenyl) -5-trifluoromethylpyridine and 5.5 g of pyridine hydrochloride are subjected to stirring for two hours at a temperature of 200 ° C. After cooling, the reaction mixture is subjected to 100 ml, thoroughly, then the solids fraction is separated and purified by column chromatography on silica gel (cyclohexane / methyl tert.butyl ether (2: 1) as eluent). , 4 g (71%) of white crystals with a melting point of 155-157 ° C.! H-NMR (250 MHz, in d6-dimethylsulfoxide): d [ppm] = 7.28 (d, 1H), 7.48 (s, 1H), 7.79 (d, 1H), 8.62 (s, 1H), 9.06 (s, 1H), 11.49 (s, 1H) Example 2 3-chloro -2- (4-cyano-3-cyclopropylcarbonylmethoxyphenip-5-trifluoromethyl-pyridine (No. Ih.09) A mixture of 1.5 g of 3-chloro-2- (4-cyano-3-hydroxy phenyl) -5 - trifluoromethylpi Ridin, 1.2 g of bromomethyl-cyclopropyl ketone, 1.5 g of potassium carbonate and 50 ml of water-free dimethylformamide was stirred for 40 hours at a temperature of 23 ° C. After the addition of 200 ml of water, it was extracted three times with 50 ml of methyl tert-butyl ether each time. The combined organic phases were washed with 50 ml of water, then dried over sodium sulfate, and recovered. The remaining residue was brought to crystallization by its treatment with n-hexane. Yield: 1.6 g of white crystals with a melting point of 115 - 116 ° C. Application Examples (Herbicidal efficacy) The herbicidal efficacy of the substituted 2-phenylpyridines I could be demonstrated by the following greenhouse tests: Flower pots were used as plastic culture vessels, provided with silty sand and with approximately 3 per cent. Hundreds of humus, as a substrate. The seeds of the various test plants were seeded separately according to their species. For the pre-emergency treatment, the active substances, suspended or emulsified in water, were applied directly after sowing, by means of very thin distribution nozzles. The containers were lightly watered, in order to stimulate germination and development, and then covered with transparent plastic caps, until the plants were grown. This coating has the effect of uniform germination of the test plants, insofar as it was not influenced by the active substance.

For the post-emergency treatment, we proceeded in the first instance to cultivate the test plants, depending on their growth mode, up to a height of 3 to 15 cm, only after which they were treated with the suspended active substances or emulsified in water. For this, the test plants were either directly seeded and cultivated in the same pots, or they were first cultivated as seedlings and transplanted a few days before the treatment, in the test vessels.

The amount applied for the post-emergency treatment was 0.0156 or 0.0078 kg of active substance per hectare. The plants were maintained, depending on their species, at temperatures of 10 to 25 ° C, or 20 to 35 ° C, respectively. The trial period ranged from 2 to 4 weeks. During this period, the plants were subject to care, and their reaction to each of the individual treatments was evaluated. The evaluation was made on a scale of 0 to 100. The number "100" indicates that the plant did not emerge, or that its aerial parts were completely destroyed, and "O" indicates that there were no damages , or that the development of the vegetable followed its normal course. The plants used in the greenhouse trials consisted of the following species: Applied in the post-emergency treatment in an amount of 0.0156 or 0.0078 kg of active substance per hectare, Compounds No. Ia.09 and No. Ih.09 showed a very good effect against the plants just indicated. Application Example (Effectiveness as Desiccant / Defoamer) As young plants under test, young 4-leaf cotton plants (without germination leaves) were used, which had been grown under greenhouse conditions (relative ambient humidity: 50 to 70%, diurnal / night temperature: 27/20 ° C) The young cotton plants received a wet foliar treatment with dripping, with aqueous preparations of the active substance (under the addition of 0, 15% by weight of the alkoxylate of fatty alcohol Plurafac LF 700, referred to the "broth" of the spray.) The amount of water applied, was equivalent to 1000 liters / hectare After 13 days the amount of fallen leaves was determined, and the degree of leaflessness was determined mathematically (defoliation), in percentage In the control plants, which did not receive treatment, leaf fall was not observed.

Claims (12)

1. R E I V I N D I C A C I O N S 1. Substituted 2-phenylpyridines characterized in that they correspond to the following General Formula I: in which the variables have the following meanings: n = 0, 1; R, R, R independently of each other, represent: hydrogen, halogen, Cj-C4-alkyl, C1-C4-halogen alkyl, hydroxy, Cj-C4-alkoxy, C1-C4-haloalkoxy, nitro, amino, Cj- C4- alkylamino, di- (Cj-C4-alkyl) amino, mercapto, Cj-C4-alkylthio, C1-C4-haloalkyl, cyano, carboxyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, or di- (Cj-C4-alkyl) ) - aminocarbonyl; R = hydrogen, halogen, C ^ -4-alkyl, C j -C4-halogen alkyl, cyano, nitro, amino, hydroxy, C | -C4-halogen alkoxy, mercapto, C 1 -C 4 -alkylthio, C j C4-haloalkyl-alkyl, C-C4-alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C j -C 4 -alkylsulfonyl, or C j -C 4 -haloalkylsulfonyl; R = hydrogen, cyano or halogen;
2. R and R independently from each other represent hydrogen or halogen;
3. R = represents: hydrogen, nitro, cyano, hydroxy, trifluoromethylsulfonyloxo, halogen, C1-C4-alkyl, Cj-C4-haloalkyl, C4-alkoxy or Cj-C4-halogen alkoxy; X = hydrogen or sulfur; R, R = independently of each other, represent hydrogen or Cj-C4-alkyl; m = represents 1, 2, 3 or 4; R = Cj-C6-alkyl, C3-C6-cycloalkyl, C C ^ halogen alkyl having from one to 5 halogen atoms; C2-C4-alkenyl, C2-C4-halogenoalkenyl with 1 to 3 halogen atoms, (Cj-C4-alkoxy) carbonyl, (C 1 -C 4 -alkoxy) carbonyl- (C j -C 4 -alkyl) -, phenyl unsubstituted or substituted one to three times, thienyl, phylanyl, tetrahydrofylaryl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, thiazoyl, isothiazolyl, pyridyl or pyrimidyl, unsubstituted or substituted one to three times, in each case , the substituents being selected from the group consisting of nitro, halogen, C1-C4-alkyl and C1-C4-alkoxy; 12 1 R, R, independently of each other, represent C1-C4-alkoxy or C C ^ alkylthio, or, together with the carbon atom in common with which they are linked, may represent a carbonyl group, a group:
4. \ C = N - O Rl * / where R: hydrogen, C1-C4-C2-C6 alkyl-alkenyl, C2-C6-halogen-alkenyl with one to three halogen atoms, (CC ^ alkox ^ carbonp Cj-C4 -alkyl) - or benzyl, or a heterocycle:
5. Z being an ethylenic or trimethylenic chain, in which, if desired, one to four hydrogen atoms may each be substituted by C1-C4-alkyl or (Cj-C4-alkoxy) carbonyl; as well as the salts usable in agriculture, of the compounds I, insofar as they exist. 2.- 2-substituted phenylpyridines of the Formula I, according to claim 1, characterized in that: n is zero; R, R, R. Independently of each other, are hydrogen or halogen; R is halogen or Cj-C4-haloalkyl, with 1 to 5 halogen atoms; R is hydrogen or halogen, especially fluorine; R is hydrogen; R is cyano or halogen Q R is hydrogen; X is oxygen;
6. R, R independently from each other, are hydrogen or Cj-C4-alkyl; m is one; R1 1 is Cj-Cg-alkyl or C3-C6-cycloalkyl; R and R, together with the carbon atom to which they are linked, represent the carbonyl group. 3. Use of the substituted 2-phenylpyridines of Formula I and the salts of I used in agriculture, according to claim 1, as herbicides or for the dissection and / or defoliation of plants. 4. Composition herbicide, characterized in that it contains a herbicidally effective amount, of at least one substituted 2-phenylpyridine of Formula I, or of a salt of I used in agriculture, according to the claim 1, and at least one inert, liquid and / or solid carrier material, and optionally also at least one surface-active material. 5. Composition for the dissection and / or defoliation of the plants, according to claim 4, characterized in that it contains an amount effective from the dissecting and / or defoliant point of view, of at least one substituted 2-phenylpyridine of Formula I, or of an I salt usable in agriculture, according to claim 1, and at least one inert, liquid and / or solid carrier material, and optionally also at least one surface-active material. 6. Process for the preparation of effective compositions as herbicides, according to claim 1 to 4, characterized in that an effective amount from the herbicidal point of view of at least one substituted 2-phenylpyridine is mixed with each other. Formula I, or a salt of I useable in agriculture, according to claim 1, with at least one inert material, liquid and / or solid, and optionally also with at least one super fi cial material. active.
7. 7. Process for the preparation of effective compositions as desiccants and / or defoliants, according to claim 1 to 5, characterized in that an amount effective from the point of view of dissectant and / or defoliant, of at least one of them, is mixed with one another. a substituted 2-phenylpyridine of Formula I, or of an I salt usable in agriculture, according to claim 1, with at least one inert, liquid and / or solid carrier material, and optionally also with less a surface-active material.
8. 8. Process to combat the growth of undesirable plants, characterized in that an herbicidally effective amount of at least one substituted 2-phenylpyridine of Formula I, or a salt of I used in the agriculture, on the plants, on the vital space of the same, or on the seeds.
9. 9. Procedure for the dissection and / or defoliation of the plants, characterized in that an effective quantity from the dissecting and / or defoliant point of view of at least one substituted 2-phenylpyridine of Formula I, or a salt of I usable in agriculture, according to claim 1, on plants.
10. 10. Process according to claim 9, characterized in that the plant subjected to treatment is cotton.
11. 11. Process for the preparation of the substituted 2-phenyl pyridines of the Formula I according to claim 1, characterized in that it is reacted in a known manner in a solvent or diluent, inert, optionally in the presence of a base, a 3-pyridyl (thio) phenol of Formula III: with an alkylating agent of Formula IV: wherein L represents chloro, bromo, iodo, methylsulfonyl oxy, trifluoromethylsulphonyloxy, phenylsulphonyloxy or p-tolyl sulfonyloxy.
12. 12. Process for the preparation of the substituted 2-phenyl pyridines of Formula I according to claim 1, wherein n is 1 and X represents oxygen, characterized in that the corresponding 2-phenyl substituted pyridines are oxidized in which n is zero and X represents oxygen, in known manner in a solvent or diluent, inert. 10 L5 0 SUMMARY Substituted 2-phenylpyridines of the following Formula (I): wherein: n = 0, 1; R1, R3, R4 = H, OH, SH, N02, NH2, CN, COOH, CONH2, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, aylcyclic, haloalkyl, alkylaminocarbonyl, dialkylaminocarbonyl; R 2 = H, OH, SH, N 2, NH 2, CN, halogen, alkyl, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkyl sulfinyl, alkylsulfonyl, haloalkylsulfonyl; R5 = H, CN, halogen; R6, R8 = H, halogen; R7 = H, OH, N02, CN, CF3-S02-0-, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy; X = oxygen or sulfur; R9, R10 = H, alkyl; m = from 1 to 4: R = alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkoxycarbonyl, alkoxycarbonylalkyl-phenyl, thienyl, furanyl, tetrahydrofanyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl or pyrimidyl, optionally substituted, in which by way of substituents it is possible to resort to N02, CN, halogen, alkyl and alkoxy; R 1 7, R 1 3 = alkoxy, alkylthio, or, together with the carbon atom in common: C = O,? = N - O - R1 R = H, alkyl, alkenyl, haloalkenyl, alkoxycarbonylalkyl, benzyl; Z = ethylenic or trimethylenic chain, optionally substituted; as well as its salts. Application: as a herbicide; for the dissection / defoliation of plants.