MXPA97004926A - 2-substitute phenilpiridines, procedure parasu obtaining and the herbicidal compositions that contain them - Google Patents

2-substitute phenilpiridines, procedure parasu obtaining and the herbicidal compositions that contain them

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Publication number
MXPA97004926A
MXPA97004926A MXPA/A/1997/004926A MX9704926A MXPA97004926A MX PA97004926 A MXPA97004926 A MX PA97004926A MX 9704926 A MX9704926 A MX 9704926A MX PA97004926 A MXPA97004926 A MX PA97004926A
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Mexico
Prior art keywords
alkoxy
alkyl
carbonyl
aminocarbonyl
halogen
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MXPA/A/1997/004926A
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Spanish (es)
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MX9704926A (en
Inventor
Misslitz Ulf
Klintz Ralf
Heistracher Elisabeth
Schafer Peter
Hamprecht Gerhard
Walter Helmut
Westphalen Karlotto
Konig Hartmann
Original Assignee
Basf Ag 67063 Ludwigshafen De
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Priority claimed from DE19500760A external-priority patent/DE19500760A1/en
Application filed by Basf Ag 67063 Ludwigshafen De filed Critical Basf Ag 67063 Ludwigshafen De
Publication of MX9704926A publication Critical patent/MX9704926A/en
Publication of MXPA97004926A publication Critical patent/MXPA97004926A/en

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Abstract

Substituted 2-phenylpyridines of the following formula (I): in which: n = 0.1, R1, R3, R4 = H, OH, SH, NO2, NH2, CN, COOH, CONH2, halogen, haloalkyl alkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, alkylthio, haloalkylthio, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, R 2 = H, OH, SH, NO 2, NH 2, CN, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsufinyl, haloalkyl sulfinyl, alkylsulfonyl, haloalkylsulfonyl, R5 = H, CN, halogen, R6, R13 = H, halogen, X = -CH-, -CO-, R7, R8, R9, R10 = H, No2, CN, halogen, alkyl , haloalkyl, alkoxy, halogenoalkoxy, R11 = H, OH, NO2, NH2, NHOH, CN CHO, COOH, COCl, CONH2, 1-pyrrolidinylcarbonyl, 1-piperidinylcarbonyl, 4-morphonylcarbonyl, 2-hydroxycarbonyl-pyrrylidin-1-yl- carbonyl, halogen or various organic radicals: R12 = H, NO2, NH2, NHOH, alkylsulfonylamino, dialkyl sulfonyl amino, halogenoalkylsulfonylamino, alkoxycarbonyl hal Oxygen alkyl, alkoxycarbonylhalongen alkenyl, as well as their salts with the exception of those I, in which R5, R7, R11, R13 represent, all of them, hydrogen, whether R7 and R10orR11, represent fluorine. Application: as a herbicide, for the dissection / defoliation of plant

Description

"2-SUBSTITUTE PHENILPIRIDINES, PROCEDURE FOR THEIR OBTAINING AND THE HERBICIDAL COMPOSITIONS THAT CONTAIN THEM Description The present invention relates to novel 2-phenylpyridines of the following Formula I: in which the variables have the following meanings: n = 0, 1; R1, R3, R4 independently of each other, represent: hydrogen, halogen, C1-C4-alkyl, C1-C4-halogen alkyl, hydroxy, C1-C-alkoxy, C1-C-haloalkoxy, nitro, amino, C1-C- alkylamino, di- (C1-C4-alkyl) amino, mercapto, CC ^ -alkylthio, CyC-haloalkyl, cyano, hydroxycarbonyl, (C1-C4-alkoxy) carbonyl, aminocarbonyl, Cj-C4-alkylaminocarbonyl, or di- (C? -C-alkyl) aminocarbonyl; R2 = hydrogen, halogen, C1-C-alkyl, C1-C4-halogen alkyl, cyano, nitro, amino, hydroxy, C1-C4-halogen alkoxy, mercapto, Cj-C4-alkylthio, Cj ^ -halogenalkylthio, Cj ^ - alkylsulfinyl, C? -C4-haloalkylsulfinyl, Cj-C4 -alkylsulfonyl, or C1-C4-haloalkylsulfonyl; R = hydrogen, cyano or halogen; R and R independently from each other represent hydrogen or halogen; X = methylene or carbonyl; R 7, R 8, R 9, R 10, independently of each other, represent: hydrogen, nitro, cyano, halogen, Cj-C ^ -alkyl, CC ^ -haloalkyl, 02-04-3100x1 or C? -C4-halogen alkoxy; R1 = hydrogen, halogen, C ^ -C ^ -alkyl, C1-C4-halogen alkyl; C ^ -C ^ - hydroxyalkyl, Cj ^ -alkoxy-Cj ^ -alkyl, C3-C6-cycloalkyl, C2-C4-alkenylC2-C4-alkynyl, hydroxycarbonyl-C1-C4-alkyl, hydroxycarbonyl-C2-C4-alkenyl, hydroxycarbonyl-C2-C4-alkynyl, (Cj ^ -alkoxy) carbonyl-C? -4-alkyl, (C? -C4-alkoxy) carbonyl-C2-C4-alkenyl, (C1-C4-alkoxy) carbonyl-C2 -C4-alkynyl, (Cj ^ -alkoxy) carbonyl-C2-C4-haloalkyl, carbonyl-C2-C4-haloalkenyl, aminocarbonyl-C1-C4-alkyl, aminocarbonyl-C2-C4-alkenyl, aminocarbonyl-C2-C4-alkynyl , C 4 -C 4 -alkylaminocarbonyl-C j -C-alkyl, C j -C ^ -alkylaminocarbonyl-C ^ -alkenyl, Cj ^ -alkylaminocarbonyl- C 2 -C 4 -alkynyl, di- (C 1 -C 4 -alkyl) - aminocarbonyl-C-C-alkyl, di- (C j -C4) -aminocarbonyl-C2-C-alkenyl, di (Cj - ^ - alkyl) aminocarbonyl-C2-C4-alkynyl, amino carbonyl-C j -C4- haloalkyl, aminocarbonyl-C2-C4-halogen alkenyl, C-C4-alkylaminocarbonyl-C j -C4-halogen alkyl, C j -C4- alkylaminocarbonyl-C2-C4-halogen alkenyl, di- (Cj-C4-alkyl) aminocarbonyl- C2-C4-ha alkyl, di- (C? -C4-alkyl) aminocarbonyl-C2-C4-halogen alkenyl, (hydroxycarbonyl-C-C4-alkyl) -aminocarbonyl-C2-C4-alkenyl, (hydroxycarbonyl-C-C4-alkyl) ) aminocarbonyl-C2-C4-haloalkenyl, N- (hydroxycarbonyl-C-C4-alkyl) -N- (C j -C4-alkyl) -aminocarbonyl-C2-C4-alkenyl, N- (hydroxy carbonyl-C j -C4 -alkyl) -N- (C j -C 4 -alkyl) aminocarbonyl-C 2 -C 4 -haloalkenyl, [(C j -C 4 -alkoxy) carbonyl-C j -C 4 -alkyl] -aminocarbonyl-C 2 -C 4 -alkenyl, [ (C -C 4 -alkoxy) carbonyl-C j -C 4 -alkyl] -aminocarbonyl-C 2 -C 4 -haloalkenyl, N - [(Cj-C 4 -alkoxy) carbonyl-C j -C 4 -alkyl] -N- (C j -C 4 -alkyl) -amino carbonyl-C ^ -alkenyl, N- [(C j -C 4 -alkoxy) carbonyl-C j -C -alkyl] -N- (C j -C 4 -alkyl) aminocarbonyl-C 2 - C 4 -halogen alkenyl, alkoxy) carbonyl] -pyrrolidin-1-l-carbonyl-C 2 -alkenyl, 2 - [(C 1 -C 4 -alkoxy) carbonyl] -pyrrolidin-1-yl-carbonyl-C 2 -C 4 haloalkenyl, formyl, (C j -C 4 -alkyl) carbonyl, (C j -C 4 -haloalkyl) carbonyl, hydroxyimino-C-C 4 -alkyl, C j -C 4 -alkyl xiimino-C j -C 4 -alkyl, 1,1-di (C j -C 4) -C j -C 4 -alkyl, 1,1 -di- (C j -C 4 -alkylo) -C 1 -C 4 -alkyl , nitro, hydroxyamino, amino, Cj-C4-alkylamino, C3-C6-cycloalkylamino, di (C1-C4-alkyl) amino, (CpC4-aIq11.il) carbonylamino, (C1-C4-haloalkyl) carbonylamino, Cj ^ - 'alkylsulfonylamino, di (C1-C4-alkyl sulfonyl) amino, Cj-C4-halogenoalkylsulfonylamino, hydroxy ,, Cj-C4-alkoxy, C4-haloalkoxy, cyano-C2-alkoxy, C1-C4-C1-C4 alkoxy -alkoxy, Cj-C -alkylthio-C1-C4-alkoxy, C3-C6-cycloalkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, hydroxycarbonyl, C! -C4-alkoxy, (C-Cg-alkoxy-arbonyl- Cj ^ -alcoxy, Cj ^ -alc xi-CCj ^ -alkoxy) carbonyl-C | -C4-alkoxy, (C j -C 4 -alkoxy) carbonyl- (C -C 4 -alkoxy) carbonyl-C j -C 4 -alkoxy, aminocarbonyl-Cj-C ^ -alkoxy, Cj - (^ - alkyl aminocarbonyl-Cj-C4-alkoxy, di (C1-C4-alkyl) amino carbonyl-C j ^ -alkoxy, 1-pyrrolid-nyl-carbonyl-C C4-alkoxy, 1-piperidinyl-carbonyl-Cj ^ -alkoxy, 4-morpholinyl carbonyl-C-C4-alkoxy, aminocarbonyl- (C-C4-alkoxy) carbonyl-C j -C4-alkoxy, (C -C 4 -alkyl) aminocarbonyl- (C j -C 4 -alkoxy) carbonyl-C j -C 4 -alkoxy, di (C j -C 4 -alkyl) aminocarbonyl- (C j -C 4 -alkoxy) carbonyl-C C 4 -alkoxy, 1- pyrro lidinyl carbonyl- (C1-C4-alkoxy) carbonyl-C? -C4-alkoxy, 4-morpholinylcarbonyl- (C1-C4-alkoxy) carbonyl-C-C4-alkoxy, [(C-C4-alkoxy) carbonyl -C -C4-alkyl] aminocarbonyl-C-C4-alkoxy, N - [(C j -C 4 -alkoxy) carbonyl-C j -C 4 -alkyl] -N- (C-C 4 -alkyl) aminocarbonyl-C -C 4 -alkoxy, [2 - [(C j -C 4 -alkoxy) carbonyl] -pyrolidin-l-yl] carbonyl-C 1 -C 4 -alkoxy, cyano, hydroxycarbonyl, COCÍ, (C 1 -C 4 -alkoxy) carbonyl, halogenoalkoxy) carbonyl , C1-C4-alkoxy- (C1-C-alkoxy) carbonyl, aminocarbonyl, Cj ^ -alkylaminocaibonyl, di- (C1-C4alkyl) -aminocarbonyl, C-Cg-cycloalkyl aminocarb onyl, 1-pyrrolidinylcarbonyl, 1-piperodinylcarbonyl, 4-morpholinylcarbonyl, hydroxycarbonyl-C-C4-alkylaminocarbonyl, N- (hydroxycarbonyl-C j -C 4 -alkyl) -N- (C j -C 4 -alkyl) -aminocarbonyl, (C j -C 4 -alkoxy) carbonyl-Cj ^ -alkylaminocarbonyl, N - [(C] -C 4 -alkoxy) carbonyl-C 1 -C 4 -alkyl] -N- (C 1 -C 4 -alkyl) -aminocarbonyl, 2- hydroxy carbonyl pyrrolidin-1-yl-carbonyl, 2 - [(Cj-C4-alkoxy) carbonyl] -pyridin-1-yl-carbonyl, or a RU group Y (Alk in which Formula: Y and Z, independently of each other, represent oxygen or sulfur; R represents hydrogen, C 1 -C 4 -alkyl or (4-alkoxycarbonyl, and Alk represents an ethylenic or trimethylenic chain, in which one or more hydrogen atoms can be replaced individually by C 1 -C 4 -alkyl or alkoxycarbonyl; R1 = hydrogen, nitro, amino, hydroxylamino, Cj ^ -alkylsulfonylamino, di- (C j -C4-alkylsulfonyl) amino, C j -C4-halogenoalkylsulfonylamino, (C j -C4-alkoxy) carbonyl-C1- C4-haloalkyl or (Cj ^ -alcox ^ arbonyl ^^ - halogen alkenyl, with the proviso that R ', R, R, and R, can not all simultaneously represent hydrogen, or that R and R, or R and R can not simultaneously represent fluorine, as well as the salts usable in agriculture, of the compounds I, insofar as they exist.Furthermore, the present invention also refers to: the use of the compounds I ', corresponding F to the definition of I without the proviso, as herbicides and / or for the dissection and / or defoliation of p latents; - 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 '. - procedures for the preparation of Compounds I, of herbicidal agents and of agents for the dissection and / or defoliation of plants, by using Compounds I '; and - the use of intermediate products II, for the preparation of compounds I. Up to now, 2-phenylpyridines of the type of Compounds I have been described in the technical literature, such as fluid crystals and pharmaceuticals. Fluid crystals, whose general formulas also encompass 2-phenylpyridines, have been mentioned in, for example, the following forms: DE-A 38 07 955, DE-A 39 15 804, DE-A 42 36 103, EP-A 283 326 , EP-A 433 826, EP-A541 081, JP-A 63/048 254, JP-A 63/254 182, JP-A 63/313 768, JP A 01/066 161, JP-A-01/070 455, JP-A05 / 331 143 and Mol. Cryst. Liq. Cryst 62 (1-2), 103-114 (1980). The 2-phenylpyridines with a pharmacological effect have been treated in for example: DE-A 25 12 673, DE-A 30 35 259, BE-A 885 484, EP-A 274 654, EP-A 039 892 and WO 92 / 06085. On the other hand, 2-phenylpyridines structurally similar to compounds I have been described in DD-A 251 206, in J. Chem. Res., Synop. 3, 86, 1994 and Izv. Timiryazevk S. Kh. Akad. 3, 155-160 (1990).
Finally, in the German Patent Application, above, DE-A 43 23 916, it is disclosed that certain 2- (4-hydroxyphenyl) pyridines, inter alia, compounds of Formula II ': in which: R represents halogen, cyano, nitro, C | ^ -alkyl, C1-C4-haloalkyl, Cj ^ -alkoxy, Cj-C4-halogen alkoxy, Cj ^ -alkylthio or Cj-C4- halogenoalkylthio; R, represents hydrogen, nitro, amino, cyano, hydroxy, mercapto, hydroxycarbonyl, halogen, Cj ^ -alkyl, Cj-C4-haloalkyl, CyC -alkoxy, C j -C4-halogen alkoxy, C j -C4 -alkylame.no , di- (C j -C 4 -alkyl) -amino, Cj-C -alkylthio, ^^ -halogenalkylthio or (C'1-C4-alkoxy) carbonyl; R represents hydrogen or halogen; and R 12 represents nitro, amino, Cj ^ -alkylsulfonylamino, or? - CyC ^ -alkylsulfonyl) amino, C1-C4-haloalkylsulfonylamino, (C1-C4-alkoxy) carbonyl-CH- (halogen) -CH2-, (C1 -C4-alkoxy) carbonyl-C (halogen) = CH-, (C, -C4) carbonyl-CH = C (halogen) or (CrC4-alkoxy) carbonyl-C (halogen) = C (halogen) -are effective as herbicides and dissecans / defoliants. 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 is 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 above, the substituted 2-phenyl-pyridines of Formulas I or I 'were discovered., respectively, with a herbicidal effect, defined in the foregoing. We also discovered herbicide agents, which contain the compounds I ', and which have a very good herbicidal effect. Procedures for the preparation of said agents, and methods for combating the development of unwanted plants, have also been discovered by the compounds I '. On the other hand, it has been discovered that the compounds I 'are also suitable for defoliation and dissection of specific parts of plants, specifically taking into account crop plants such as cotton, potatoes, rapeseed, sunflower, soybeans or beans. , especially of 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 , they 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 furthermore the phosphonium salts, the sulfonium salts such as preferably the tri (C? -C4-alkyl) sulfonium salts, and the sulfoxonium salts such as, preferably, the tri- ( C1 -C4-alkyl) sulfoxonium. Among the acid addition salts, mention may first be made of the hydrochlorides, hydrobromides, sulfates, nitrates, phosphates, oxalates and the dodecylbenzolesulfonates. The following designations used for the definition of the substituents R to R1 or of the aforementioned organic molecules in the Alk chain, ie: alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxy alkoxy, alkylthio, haloalkylthio, alkylamino, dialkyl amino, cycloalkyloxy, cycloalkylamino, diC amino, alkoxycarbonyl, alkoxycarbonyloxy, alkylcarbonyl oxy, halógenoalquilcarboniloxi, cycloalkyl-carbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylamino carbonyloxy, dialquilaminocarbonilam.no, alkylsulfinyl, halo-alkylsulfinyl, alkylsulfonyl, haloalkyl sulfonyl, alkylsulfonyloxy, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylamino and alkynylamino, represent- same as the meaning halogen-, 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 and iodine; Cj-C4-alkyl, as well as the alkyl part of (Cj ^ -alkoxy-C i ^ -alkyl, CpC ^ alkylaminocarbonyl-C j -C4-alkyl, C-C4-alkylaminocarbonyl-C2-C4-alkenyl, C | -C4-alkylaminocarbonyl-C2-C4-alkynyl, N- (hydroxycarbonyl-C-C4-al-quyl) -N- (C j -C4-alkyl) aminocarbonyl-C2-C4-alkenyl, N- (hydroxycarbonyl) -C j -C 4 -alkyl) -N- (C j -C 4 -alkyl) amino carbon il-C 2 -C 4 -haloalkenyl, [(C j -C 4 -alkoxy) carbonyl-C j -C-alkyl] -aminocarbonyl- C2-C4-alkenyl, N- [(C j -C4-alkoxy) carbonyl-C j -C 4 -alkyl] -N- (C 1 -C 4 -alkyl) -aminocarbonyl-C 2 -C 4 -alkenyl [(C j - C4-alkoxy) carbonyl-C ^ -4-alkyl] -aminocarbonyl-C2-C4-haloalkenyl, N - [(C-C4-alkoxy) carbonyl-C j -C4-alkyl] -N- (C j -C4- alkyl) amino carbonyl-C2-C4-halogenoalkenyl, C j -C4-alkoxyimino-C j -C 4 -alkyl, 1, 1 -di- (C j -C 4 -alkoxy) -C ^ -C -alkyl, 1., 1 -di- (C j -C -alkylthio) -C j -C 4 -alkyl, [(C 4 -C 4 -alkoxy) carbonyl-C j -C 4 -alkyl] -aminocarbonyl-C j -C 4 -alkoxy, N- [(C j -C 4 -alkoxy) carbonyl-C j -C 4 -alkyl] -N- (C j -C 4 -alkyl) -aminocarbonyl-C j -C 4 -alkoxy and N- (hydroxycarbonyl-C j -C 4 -alkyl) -N- (C j -C 4 -alkyl) -amino-carbonyl, N- [(C -C 4) alkoxy) carbonyl-C j -C 4 -alkyl] -N (- (C j -C 4 -alkyl) -aminocarbonyl and di (C j -C 4 -alkyl) aminocarbonyl- (C j -C 4 -alkoxy) carbonyl-C j - C4-alkoxy, represent: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methyl propyl, or 1,1-dimethylethyl; C1-C4-haloalkyl, as well as the haloalkyl part of aminocarbonyl-C? -C 4 -haloalkyl and C j -C 4 -alkylaminocarbonyl-C 4 -C 4 -haloalkyl represent: a C 1 -C 4 -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-trifluoromethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoromethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, penta fluorethyl, 2- fluoropropyl, 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-pentafluoropropyl, heptafluopropyl, 1- (fluorine methyl) -2-fluoroethyl, l- (chloromethyl) -2-chloroethyl, 1- (bromo methyl) -2-bromomethyl, 4-fluorbutyl, 4-chlorobutyl, 4-bromobutyl or nona fluorbutyl; the C1-C4-halogenoalkyl part of (Cj-C4-alkoxy) carbonyl-C2-C4-haloalkyl and di- (C1-C4-alkyl) aminocarbonyl-C2-C4-halogenoalkyl, represents: a radical partially or wholly substituted by fluorine, chlorine, bromine and / or iodine, that is, for example: ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylproyl or 1,1-dimethylethyl, ie, for example, : 2-fluoroethyl, 2-chloroethyl, 2-bromo methyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-di-chloro-2-fluor-ethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3 -dichloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluopropyl, heptafluofropyl, - (fluoromethyl) -2-fluoryl ethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromoethyl, 4-fluorbutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorbutyl; C j -C 4 -alkoxy, as well as the alkoxy portions of (C 4 -C 4 -alkoxy-C j -C 4 -alkyl, C j -C 4 -alkoxy-C j -C 4 -alkoxy, C j -C 4 -alkyl thio- C j -C -alkoxy, (C j -C-alkoxy) carbonyl, (C j -C 4 -alkoxy) carbonyl-C? -C 4 -alkyl, (C j -C 4 -alkoxy) -carbonyl-C 2 -C 4 -alkenyl , (C j -C 4 -alkoxy) carbonyl-C 2 -C 4 -alkynyl, (C 4 -C 4 -alkoxy) carbonyl-C 2 -C 4 -haloalkyl, (C j -C 4 -alkoxy) carbonyl-C 2 -C 4 -halogenolkenyl, ( C1-C4-alkoxy) carbonyl-C1-C4-alkyl] aminocarbonyl-C2-C4-alkenyl, N - [(C j -C4-alkoxy) carbonyl-C ^ -C4-alkyl] -N- (C j -C -alkyl) amino carbonyl-C2-C-alkenyl, (C1-C4-alkoxy) carbonyl-C1-C4-alkyl] -aminocarbonyl] -C2-C4-haloalkenyl, N - [(C j -C4-alkoxy) carbonyl- C j -C 4 -alkyl] -N- (C j -C 4 -alkyl) -amino carbonyl-C 2 -C 4 -haloalkenyl, 2 - [(C-C 4 -alkoxy) carbonyl-pyrrolidin-1-l-carbonyl-C 2- C4-alkenyl, 2 - [(C -C-alkoxy) carbonyl] -pyrrolidin-1-ii-carbonyl-C2-C4-halogen alkenyl, (C-C4-alkoxy) carbonyl-C j -C4-alkoxy, C ^ -C4-alkoxy (C ^ -4-alkoxy) carbonyl-C-C4-alc oxy, (Cj-C4-alkoxy) carbonyl- (C1-C4-alkoxy) carbonyl-C1-C4-alkoxy, Cy C4-alkoxy-imino-C-alkyl, 1,1-di (C j -C4-alkoxy) ) -C -C -C4-alkyl, C j -C-alkylaminocarbonyl-C ^ -C4-alkoxy, di (C j -C -alkyl) -aminocarbonyl-C -C4-alkoxy, [(C j -C4-alkoxy) carbonyl-C-C 4 -alkyl] -aminocarbonyl-C-C 4 -alkoxy, N - [(C j -C 4 -alkoxy) carbonyl-C j -C 4 -alkyl] -N- (C j -C 4 -alkyl) -aminocarbonyl -C j -C 4 -alkoxy, [2- (C j -C 4 -alkoxy) carbonyl] pyrrolifidin-1 -yl] carbonyl-C j -C 4 -alkoxy, C 1 -C 4 -alkoxy- (C 1 -C 4 -alkoxy) carbonyl , (C 1 -C 4 -alkoxy) carbonyl-C 1 -C 4 -alkylaminocarbonyl, N - [(C j -C 4 -alkoxy) carbonyl-C j -C 4 -alkyl] -N- (C j -C 4 -alkyl) -aminocarbonyl , 2 - [(C 1 -C 4 -alkoxy) carbonyl] -pyrrolidin-1-yl-carbonyl, aminocarbonyl- (C j -C 4 -alkoxy) carbonyl-C j -C 4 -alkoxy, (C j -C 4 -alkyl) aminocarbonyl - (C1-C4-alkoxy) carbonyl-C? -C4-alkoxy, d ^ Cj ^ -alkyl) -aminocarbonyl- (C j -C4-alkoxy) carbonyl-C j -C4 -alkoxy, 1-pyrrolidinylcarbonyl- (C j -C4-alkoxy) carbonyl-C j -C 4 -alkoxy-1-piperidinylcarbonyl- (C j -C 4 -alkoxy) carbon yl-C-C4-alkoxy, 4-morpholinylcarbonyl- (C j -C4-alkoxy) carbonyl-Cj ^ -alkoxy, represent: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy; Cj-C4-halogenoalkoxy represents: Cj-C ^ -alkoxy as mentioned above, which is totally or partially substituted by fluorine, chlorine, bromine and / or iodine, ie, for example: difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoromethoxy, 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-pentane fluorine propoxy, heptafluofropoxy, 1 - (fluorine methyl) -2-fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nona fluoride buto xi; cyano-C 1 -C 4 -alkoxy, represents: cyanomethoxy, 1-cyanoet-1-yloxy, 2-cyanoet-1-yloxy, 1-cyanoprop-1-yloxy, 2-cyanoprop-1-yloxy, 3-cyanopropyl l-iloxy, l-cyanoprop-2-yloxy, 2-cyanoprop-2-yloxy, 1-cyanobut-l-yloxy, 2-cyanobut-l-yloxy, 3-cyanobut-l-yloxy, 4-cyano-l- Ioxy, l-cyanobut-2-yloxy, 2-cyanobut-2-yloxy, l-cyanobut-3-yloxy, 2-cyanobut-3-yloxy, 1-cyano-2-methyl-prop-3-yloxy, 2- cyano-2-methyl-prop-3-yloxy, 3-cyano-2-methyl-prop-3-yloxy or 2-cyanomethyl-prop-2-yloxy; The alkyl, as well as the alkylthio portions of 1, 1-di- (C 1 -C 4 -alkylthio-C 1 -alkyl and C 1 -C 4 -alkylthio-C 1 -C 4 -alkoxy, represent: methylthio, ethylthio, n-propylthio , 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio; Cj-C4-haloalkylthio represents: 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-difluorethylthio, 2,2,2- trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoro-ethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluor ethylthio, pentafluorethylthio, 2-fluoro-propylthio, 3-fluoropropylthio, 2-Chloro-ropylthio, 3-chloropropylthio, 2-bromopropyl, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3, 3,3-trichloroprop ilthio, 2,2,3,3,3-pentafluor propylthio, heptafluoropropylthio, 1- (fluomethyl) -2-fluoroethyl thio, 1- (chloromethyl) -2-chloroethylthio, 1- (bromomethyl) -2-bromo methylthio, -fluorbutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorbutylthio; CpC 4 -alkylamino, as well as the alkylamino parts of C 1 -C 4 -alkylaminocarbonyl, C -C 4 -alkylaminocarbonyl-C j -C 4 -haloalkyl, C 1 -C 4 -alkylaminocarbonyl-C 2 -C 4 -haloalkyl, C -C 4 -alkylamino .no-carbonyl-C j -C 4 -alkoxy, (C j -C 4 -alkoxy) carbonyl-C j -C 4 -alkylaminocarbonyl and (C j -C 4 -alkyl) aminocarbonyl- (C j -C 4 -alkoxy) carbonyl -C j -C 4 -alkoxy, represent: methylamino, ethylamino, n-propyl amino, 1-methyl ethyl amino, n-butylamino, 1-methyl-propylamino, 2-methyl propyl amino, or 1,1-dimethylethylamino; Di- (C2-C4-alkyl) amino, as well as the dialkylamino parts of di- (C1-C4-alkyl) aminocarbonyl, di (CpC4-alkyl) amino carbonyl-C j-C4-alkyl, di- (Cj-C4 -alkyl) amino carbonyl-C2-C4-alkenyl, di- (Cj-C4-alkyl) amino carbonyl-C2-C4-alkynyl, di- (C4-C4-alkyl) aminocarbonyl-C2-C4-haloalkyl, di- (C -C4-alkyl) aminocarbonyl-C2-C4-halogenoalkylene and di- (C1-C4-alkyl) aminocarbonyl-C1-C4-alkoxy, represent for example: N, N-dimethylamino, N, N-diethylamino, N, N-diisopropylamino, N, N-dibutylamino, N, N-di- (l-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N, N-di- (1,1-dimethyl ethyl) ) 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- (l ~ methylethyl) amino, N-butyl-N-ethylamino, N-ethyl-N- (l-methylpropyl) amino, N-ethyl-N- (2-methyl propyl) amino, N-ethyl-N- (l, l- dimethylethyl) amino, N- (1-methyl ethyl) -N-propylamino, N-butyl-N-propylamino, N- (1-methyl propyl) -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-methylpropyl) amino, N- (1-methyl ethyl) -N- (2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N- (methyl ethylamino), N-butyl-N-methyl propyl) 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-methyl propyl amino); C1-C4-alkylsulfinyl, represents: methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulphinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropyl sulfinyl, or 1,1-dimethylethylsulphinyl; C j -C 4 -haloalkylsulfinyl, represents: C -C 4 -alkylsulfinyl as mentioned above, partially or wholly substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, difluoromethyl-sulphonyl, trifluoromethyl-sulfinyl, chlorodifluoromethyl-sulphonyl, bromodifluoromethyl-sulfinyl, -fluoroethylsulfinyl, 2-chloroethylsulfinyl, 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-difiuor ethyl sulfinyl, 2,2-dichloro-2-fluoro-methyl-sulphonyl, pentafluoroethyl-sulfinyl, 2-fluoro-propyl-sulfinyl, 3-fluoropropylsulfinyl, 2-chloro-propyl-sulfinyl, 3-chloropropyl-sulfinyl, 2-bromo-propylsulfinyl, -bromopropylsulfinyl, 2,2-difluoropropyl sulfinyl, 2,3-difluoropylsulfinyl, 2,3-dichloropropylsulfinyl, 3,3,3-trifluoropylsulfinyl, 3,3,3-trichloro propylsulfinyl, 2,2,3,3,3-pentafluor propyl sulfinyl, heptafiuofropilsulfinilo, 1 - (fluormetil) -2-fluoretilsulfinilo, 1 - (chloro methyl) -2-chloroethylsulfinyl, 1- (bromo methyl) -2-bromomethylsulfinyl, 4-fluorobutyl sulfinyl, 4-bromobutylsulfinyl or nonafluorbutylsulfinyl; C1-C4-alkylsulfonyl, as well as the alkylsulfonyl portions of Cp C4-alkylsulfonylamino and di (CpC4-alkyl sulfonyl) amino, represent: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsul-fonyl, 1-methylpropylsulfonyl, 2-methylpro? Il sulfonyl, or 1,1-dimethylethyl-sulfonyl; CpC4-halogenoalkylsulfonyl, as well as the halogenoalkylsulfonyl part of CpC4-halogenoalkyl sulfonyl amino, represent: CpC4-alkylsulfonyl as mentioned above, partially or wholly substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, difluoromethyl sulfonyl , trifluoromethylsulphonyl, chlorodifluoromethyl sulfonyl, bromodifluoromethylsulphonyl, 2-fluoroethyl sulfonyl, 2-chloroethylsulfonyl, 2-bromoethyl sulfonyl, 2-iodo-ethyl sulfonyl, 2,2-difluoroethylsulphonyl, 2,2,2-trifluoromethyl-sulfonyl, 2,2,2-trploroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoro-sulfosulfonyl, pentafluorosulfonyl, 2-fluoro-phenylsulfonyl, 3-fluoropropyl sulfonyl, 2-chloro-propylsulfonyl, 3-chloropropylsulfonyl , 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluopropylsulfonyl, 2,3-dichloro propyl sulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropyl-sulfonyl, 2,2,3, 3, 3 -pentafluor prop il-sulfonyl, heptafluoropropylsulfonyl, 1- (fluomethyl) -2-fluoro-sulfosulfonyl, 1- (chloromethyl) -2-chloroethylsulfonyl, 1- (bromo-methyl) -2-bromomethylsulfonyl, 4-fluorbutylsulfonyl, 4-bromobutyl-sulfonyl or nonafluorbutylsulfonyl; CpC4-hydroxyalkyl, represent: hydroxymethyl, 1-hydroxyethyl-1-yl, 2-hydroxyethyl-1-yl, 1-hydroxypropyl-1-yl, 2-hydroxypropyl-1-yl, 3-hydroxypropyl-1-yl, l- hydroxyprop-2-yl, 2-hydroxyprop-2-yl, 1-hydroxybutyl-l, 2-hydroxybutyl-l, 3-hydroxybutyl-l, 4-hydroxybutyl-l, 1-hydroxybutyl -2-yl, 2-hydroxybut-2-yl, l-hydroxybut-3-yl, 2-hydroxy but-3-yl, l-hydroxy-2-methyl-prop-3-yl, 2-hydroxy-2-methyl-propyl 3-yl, 3-hydroxy-2-methyl-prop-3-yl or 2-hydroxy-methyl-prop-2-yl; hydroxyimino-CpC4-alkyl, represents: hydroxy iminomethyl, 1- (hydroxy-iimino-) et-1-yl, 2- (hydroxyimino) et-1-yl, 1- (hydroxyimino) prop-1-yl, 2- ( hydroxyimino) prop-1-yl, 3- (hydroxyimino) prop-1-yl, 1- (hydroxyimino) prop-2-yl, 2- (hydroxyimino) prop-2-yl, 1- (hydroxyimino) but- 1 - ilo, 2- (hydroxy-imino) butyl-l, 3- (hydroxyimino) butyl-yl, 4- (hydroxyimino) but-1-yl, 1- (hydroxyimino) but-2-yl, 2- (hydroxyimino) but-2-yl, 1- (hydroxyimino) but-3-yl, 2- (hydroxyimino) but-3-yl, 1- (hydroxyimino) -2-methyl-prop-3-yl, 2- ( hydroxyimino) -2-methyl-prop-3-yl, 3- (hydroxyimino) -2-methyl-prop-3-yl or 2- (hydroxyimino) methyl-prop-2-yl; the hydroxycarbonyl-CpC4-alkyl part of hydroxycarbonyl-C pC4-alkylaminocarbonyl and of N- (hydroxycarbonyl-C pC4-alkyl) -N- (CpC4-alkyl) -aminocarbonyl, represents: hydroxycarbonylmethyl, 1- (hydroxycarbonyl) et-1-yl, 2- (hydroxycarbonyl) et-1-yl, 1- (hydroxycarbonyl) prop-1-yl, 2- (hydroxycarbonyl) prop-1-yl, 3 - (hydroxycarbonyl) prop-1-yl, 1- (hydroxycarbonyl) prop-2-yl, 2- (hydroxycarbonyl) prop-2-yl, 1- (hydroxycarbonyl) but-1-yl, 2- ( hydroxycarbonyl) but-l-yl, 3- (hydroxycarbonyl) butyl-l, 4- (hydroxycarbonyl) but-1-yl, 1- (hydroxycarbonyl) but-2-yl, 2- (hydroxycarbonyl) but- 2-yl, 1- (hydroxycarbonyl) but-3-yl, 2- (hydroxycarbonyl) but-3-yl, 1- (hydroxycarbonyl) -2-methyl-prop-3-yl, 2- (hydroxycarbonyl) -2- methyl-prop-3-yl, 3- (hydroxycarbonyl) -2-methyl-prop-3-yl or 2- (hydroxycarbonyl) methyl-prop-2-yl; C3-C6-cycloalkyl represents: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; C3-C6-cycloalkoxy, represents: cyclopropyloxy, cyclobutyl oxy, cyclopentyloxy or cyclohexyloxy; C3-Cg-cycloalkylamino, represents: cyclopropylamino, cyclobutylamino, cyclopentylamino or cyclohexylamino; C3-C6-cycloalkylaminocarbonyl, represents: propylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentyl aminocarbonyl or cyclohexylaminocarbonyl cycle; C2-4-alkenyl, as well as the alkenyl portions of CpC4-alkylaminocarbonyl-C2-C4-alkenyl, di- (Cj-C4-alkyl) -aminocarbonyl-C2-C4-alkenyl, (hydroxycarbonyl-C-C4-alkyl) ) -aminocarbonyl-C2-C4-alkenyl, N- (hydroxy carbonyl-C-C4-alkyl) -N- (C-C4-alkyl) aminocarbonyl-C2-C4-alkenyl, [(C-C4-alkoxy) carbom -CpC4] aminocarbonyl-C2-C4-alkenyl, N- [(CpC4-alkoxy) carbonyl-CpC4-alkyl] -N- (CpC4-alkyl) -aminoarbonyl-C2-C4-alkenyl and 2 - [(C pC4-alkoxycarbonyl ] -pyrrilidin-1-yl-carbonyl-C2-C4-alkenyl, represent: vinyl, prop-1-en-l-yl, prop-2-en-l-yl, 1-methylenyl, n-buthen- 1 - ilo, n-butén-2-yl, n-butén-3-yl, 1-methyl-prop-1-en-1-yl, or 2-methyl-prop-l-en-l-yl, the haloalkyl part of (CpC4-alkoxy) carbonyl-C2-C4-halogen-alkenyl, aminocarbonyl-C2-C4-halogen alkenyl, CpC4-alkylamino-carbonyl-C-C-halogen alkenyl, di- (C j -C-alkyl) aminocarbonyl- C2-C-halogeno alkenyl, (hydroxycarbonyl-C j -C4-alkyl) -aminocarbonyl-C2-C4-halogenoalkenyl, N- (hydroxycarbonyl-C pC4-alkyl) -N- (C pC4-alkyl) aminocarbonyl-C2-C4-haloalkynyl, [(CpC4-alkoxy) carbonyl-Cp C4-alkyl] aminocarbonyl-C2-C4-halogen alkenyl. N - [(C j -C-alkoxy) -carbonyl-C-C 4 -alkyl] -N- (C j -C 4 -alkyl) aminocarbonyl-C 2 -C 4 -halogen-alkenyl and 2 - [(C -C 4 -alkoxy ) carbonyl] -pyrrolidin-1-yl-carbonyl-C2-C4-halogenoalkenyl, represents: a C2-C4-alkenyl radical, as mentioned above, partially or totally substituted by fluorine, chlorine, bromine and / or iodine, for example: 2-chloroalyl, 3-chloroalyl, or 3,3-dichloroalyl; C2-C4-alkynyl, as well as the alkynyl portions of CpC4-alkynylcarbonyl-C2-C4-alkynyl and di (CpC4-alkyl) aminocarbonyl-C2-C4-alkynyl, represent: ethynyl, prop-1-yn-l-yl, prop-2-yn-l-yl, butyl-1-yn-lyl, but-l-in-3-yl, but-l-in-4-yl or but-2-yn-l-yl; C2-C4-alkenyloxy, represents: vinyloxy, prop-1-in-1-yloxy, prop-2-in-1-yloxy, 1-methylenynyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n-buten-3-yloxy, 1-methyl-prop-1-en-1-yloxy, 2-methyl-prop-1-en-1-yloxy, 1-methyl-prop-2-en-1-yloxy, or 2-methyl-prop-2-en-l-yloxy; C2-C4-alkynyloxy, represents: ethynyloxy, prop-1-in-1-ryloxy, prop-2-in-1-yloxy, but-1-ynyloxy, but-l-in-3-yloxy, but-l -in-4-yloxy or but-2-yn-l-yloxy; hydroxycarbonyl-C pC4-alkyl, as well as the hydroxycarbonylalkyl portions of (hydroxycarbonyl-C j -C-alkyl) aminocarbonyl-C2-C4-alkenyl, (hydroxycarbonyl-C j -C4-alkyl) -aminocarbonyl-C2-C4- haloalkenyl, N- (hydroxycarbonyl-C j -C 4 -alkyl) -N- (C j -C 4 -alkyl) -amino carbonyl-C 2 -C -alkenyl and N- (hydroxycarbonyl-C j -C 4 -alkyl) -N - (C j -C 4 -alkyl) -aminocarbonyl-C 2 -C 4 -haloalkenyl, represents: hydroxycarbonyl, 1- (hydroxycarbonyl) et-1-yl, 2- (hydroxycarbonyl) et-1-yl, 1- (hydroxycarbonyl) prop -l-ilo, 2- (hydroxycarbonyl) prop-1-yl, 3- (hydroxy-carbonyl) prop-1-yl, l- (hydroxycarbonyl) prop-2-yl, 2- (hydroxy carbonyl) prop-2 ilo, 1- (hydroxycarbonyl) but-1-yl, 2- (hydroxycarbonyl) but-1-yl, 3- (hydroxycarbonyl) but-1-yl, 4-4- (hydroxycarbonyl) but-1-yl, - (hydroxycarbonyl) but-2-yl, 2- (hydroxycarbonyl) but-2-yl, l- (hydroxycarbonyl) but-3-yl, 2- (hydroxycarbonyl) but-3-yl, l- (hydroxycarbonyl) -2-methyl prop-3-yl, 2- (hydroxycarbonyl) -2-methyl-prop-3-yl, 3- (hydroxycarbonyl) ) -2-methyl-prop-3-yl, 2- (hydroxycarbonylmethyl) -prop-2-yl; r-idroxycarbonyl-C2-C4-alkenyl, represents: 2- (hydroxycarbonyl) vinyl, 2- (hydroxycarbonyl) allyl, 3- (hydroxycarbonyl) allyl or 4- (hydroxycarbonyl) but-2-yl; hydroxycarbonyl-C2-C4-alkynyl, represents: 2- (hydroxycarbonyl) ethynyl, 3-hydroxycarbonyl-1-propynyl or 3- (hydroxycarbonyl) -2-propyne-1-yl; aminocarbonyl-C pC4-alkyl, represents: aminocarbonylmethyl, 1- (aminocarbonyl) et-l-yl, 2- (aminocarbonyl) et-1-yl, l- (aminocarbonyl) prop-1-yl, 2- (aminocarbonyl prop-1-yl, 3- (aminocarbonyl) prop-1-yl, 3- (amino-carbonyl) prop-1-yl, 1- (aminocarbonyl) prop-2-yl, 2- (amino-carbonyl) prop-2) -yl, l- (aminocarbonyl) but-l-yl, 2- (aminocarbonyl) butyl-l, 3- (aminocarbonyl) butyl, 4- (aminocarbonyl) butyl, l- (aminocarbonyl) but-l-2-yl, 2- (aminocarbonyl) but-2-yl, l- (aminocarbonyl) but-3-yl, 2- (aminocarbonyl) but-3-yl, 1 - ( aminocarbonyl) -2-methyl-prop-3-yl, 2- (aminocarbonyl) -2-methyl-prop-3-yl, 3- (aminocarbonyl) -2-methyl-prop-3-yl, or 2- (aminocarbonylmethyl ) -prop-2-yl; aminocarbonyl-C pC4-alkoxy, represents: aminocarbonyl methoxy, 1- (aminocarbonyl) et-1-yloxy, 2- (aminocarbonyl) et-1-yloxy, 1- (aminocarbonyl) prop-1-yloxy, 2- ( aminocarbonyl) prop-1-yloxy, 3- (aminocarbonyl) prop-1-yloxy, 1- (aminocarbonyl) prop-2-2-yloxy, 2- (aminocarbonyl) prop-2-yloxy, 1- (aminocarbonyl) but - 1-yloxy, 20 (aminocarbonyl) but-1-yloxy, 3- (aminocarbonyl) but-1-yloxy, 4- (aminocarbonyl) but-1-yloxy, 1- (aminocarbonyl) but-2-yloxy , 2- (aminocarbonyl) but-2-yloxy, 1- (aminocarbonyl) but-3-yloxy, 2- (aminocarbonyl) but-3-yloxy, l- (aminocarbonyl) -2-methyl-prop-3- Ioxy, 2- (aminocarbonyl) -2-methyl-prop-3-yloxy, 3- (aminocarbonyl) -2-methyl-prop-3-yl-oxy or 2- (aminocarbonylmethyl) -prop-2-yloxy; aminocarbonyl-C2-C4-alkenyl, represents for example: 2- (amino-carbonyl) vinyl, 2- (aminocarbonyl) allyl, 3- (aminocarbonyl) allyl or 4- (aminocarbonyl) but-2-yl; aminocarbonyl-C2-C4-alkynyl, represents for example: 2- (aminocarbonyl) ethynyl, 3-aminocarbonyl-1-propionyl or 3-aminocarbonyl-2-propin-1-yl; CpC 4 -alkylcarbonyl as well as the alkyl carbonyl part of (Cp C 6 -alkyl) carbonylamino, represent: methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methyl ethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or , 1-dimethylethyl carbonyl; (CpC4-haloalkyl) carbonyl, as also the alkylcarbonyl part of (C j -C6-alkyl) carbonylamino, represent: (C -C 4 -alkyl) -carbonyl as mentioned above, which is totally or partially substituted by fluorine, chlorine, bromine and / or iodine, ie, for example: chloroacetyl, dichloroacetyl, trichloroacetyl, fluorine acetyl, difluoroacetyl, trifluoroacetyl, chlorofluor acetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 1-fluorpropionyl, 2-fluorpropionyl, 2,2-difluoropropionyl, 3,3,3 trifluoropropionyl, 3-chloro-3-fluoro-propionyl, 3-chloro-3,3-difluoropropyl, 3,3-dichloro-3-fluoro-propionyl, tri-chloropropionyl or pentafluoropropionyl; hydroxycarbonyl-C pC4-alkoxy, represents: hydroxycarbonyl methoxy, 1- (hydroxycarbonyl) et-1-yloxy, 2- (hydroxycarbonyl) et-1-yloxy, 1- (hydroxycarbonyl) prop-1-yloxy, 2- ( hydroxycarbonyl) prop-1-yloxy, 3- (hydroxycarbonyl) prop-1-yloxy, 1- (hydroxycarbonyl) prop-2-yloxy, 2- (hydroxycarbonyl) prop-2-yloxy, 1- (hydroxycarbonyl) but- l -iloxy, 2- (hydroxycarbonyl) but-1-yloxy, 3- (hydroxycarbonyl) but-1-yloxy, 4-4- (hydroxycarbonyl) buyt-1-yloxy, 1- (hydroxycarbonyl) but-2 -iloxy, 2- (hydroxycarbonyl) but-2-yloxy, 1- (hydroxycarbonyl) but-3-yloxy, 2- (hydroxycarbonyl) but-3-yloxy, 1- (hydroxycarbonyl) -2-methylprop-3-yloxy , 2- (hydroxycarbonyl) -2-methyl-prop-3-yloxy, 3- (hydroxycarbonyl) -2-methyl-prop-3-yloxy or 2- (hydroxycarbonylmethyl) -prop-2-yloxy; the aminocarbonyl- (CpC4-alkoxy) amino-carbonyl- (CpC4-alkoxy) carbonyl-CpC4-alkoxy part, represents: aminocarbonylmethoxy, 1- (amino-carbonyl) et-1-yloxy, 2- (amino carbonyl) et-1 -iloxy, 1- (aminocarbonyl) prop-1-yloxy, 2- (aminocarbonyl) prop-1-yloxy, 3- (aminocarbonyl) prop-1-yloxy, 1- (aminocarbonyl) prop-2-yloxy, 2- (aminocarbonyl) prop-2-yloxy, 1- (aminocarbonyl) but-l-yloxy, 2- (aminocarbonyl) but-1-yloxy, 3- (aminocarbonyl) but-l-yloxy, 4-4- ( aminocarbonyl) but-l-yloxy, l- (aminocarbonyl) but-2-yloxy, 2- (aminocarbonyl) but-2-yloxy, l- (aminocarbonyl) but-3-yloxy, 2- (aminocarbonyl) but-3- Ioxy, 1- (aminocarbonyl) -2-methyl-prop-3-yloxy, 2- (aminocarbonyl) -2-methyl-prop-3-yloxy-3- (aminocarbonyl) -2-methyl-prop-3-yloxy or 2- ( aminocarbonyl methyl) -prop-2-yloxy; l-pyrrodinyl-carbonyl-CpC4-alkoxy, as well as the 1-pyrrolidinylcarbonylalkoxy part of 1-pyrrolidinyl carbonyl- (CpC4-alkoxy) carbonyl-CpC4-alkoxy, represent: 1-pyrrolidinylcarbonyl-methoxy, 1- (1-pyrrodinyl-carbonyl) ) et-1-yloxy, 2- (1-pyrrolidinylcarbonyl) et-1-yloxy, 1- (1-pyrrolidinyl carbonyl) prop-1-yloxy, 2- (l-pyrrolidinyl carbonyl) prop-1-yloxy, 3- (l-pyrrolidinylcarbonyl) prop-1-yloxy, 1- (1-pyrrolidinylcarbonyl) prop-2-yloxy, 2- (1-pyrrolidinylcarbonyl) prop-2-yloxy, 1- (pyrrolidinylcarbonyl) but-l-yloxy, 2- (1-pyrrolidinylcarbonyl) but-1-yloxy, 3- (1-pyrrolidinylcarbonyl) but-1-yloxy, 4-4- (1-pyrrolidinylcarbonyl) but-l-yloxy, 1- (1-pyrrolidinyl carbonyl) but -2-yloxy, 2- (l-pyrrolidinylcarbonyl) but-2-yloxy, 1- (1-pyrrolidinylcarbonyl) but-3-yloxy, 2- (1-pi? Tolidinylcarbonyl) but-3-yloxy, 1- (1 -pyrrolidinyl carbonyl) -2-methylprop-3-yloxy, 2- (1-pyrrolidinylcarbonyl) -2-methyl-prop-3-yloxy, 3- (1-pyrrolidinylcarbonyl) -2-methyl-prop-3-yloxy or - (l-pyrrolidinil carbonylmethyl) -prop-2-yloxy; 1-Piperidinyl-C 1 -C 4 -alkoxy-alkoxy, as well as the 1-piperidinylcarbonylalkoxy -piperidinylcarbonyl- (C 1 -C 4 -alkoxy) carbonyl-C -C 4 -alkoxy part, represent: 1-piperidinyl carbonyl-methoxy, 1- ( 1-piperidinyl) et-1-yloxy, 2- (1-piperidinylcarbonyl) et-1-yloxy, 1- (1-piperidinyl carbonyl) prop-1-yloxy, 2- (1-piperidinylcarbonyl) prop-1-yloxy, 3- (1-piperidinylcarbonyl) prop-1-yloxy, 1- (1-piperidinyl carbonyl) prop-2-yloxy, 2- (l -piperidinylcarbonyl) prop-2-yloxy, 1- (piperidinylcarbonyl) but- 1 - Iloxy, 2- (1-piperidinylcarbonyl) but-1-yloxy, 3- (1-piperidinyl carbonyl) but-1-yloxy, 4-4- (1-piperidinylcarbonyl) but-1-yloxy, l- (l-piperidinylcarbonyl ) but-2-yloxy, 2- (l -piperidinylcarbonyl) but-2-yloxy, 1- (1-piperidinylcarbonyl) but-3-yloxy, 2- (l-piperidinylcarbonyl) but-3-yloxy, 1- (1-piperidinylcarbonyl) -2-methylprop-3-yloxy, 2- (1-piperidinyl carbonyl) -2-methyl-prop-3-yloxy, 3- (l -piperidinyl carbonyl) -2-methyl-prop-3- iloxy or 2- (l-piperidinyl carbonylmethyl) -prop-2-yloxy; 4-morpholinylcarbonyl-CpC4-alkoxy, as well as the 4-morpholino-nilcarbonylalkoxy part of 4-morpholinocarbonyl- (C j -C4-alkoxy) carbonyl-C j -C4-alkoxy, represent: 4-morpholinyl carbonyl-methoxy, 1- (4-morpholinylcarbonyl) et-1-yloxy, 2- (4-morpholinylcarbonyl) et-1-yloxy, 1- (4-morpholinylcarbonyl) prop-1-yloxy, 2- (4-morpholinylcarbonyl) prop-1 -iloxy, 3- (4-morpholinylcarbonyl) prop-1-yloxy, 1- (4-morpholinylcarbonyl) prop-2-yloxy, 2- (l-morpholinylcarbonyl) prop-2-yloxy.l - (4-morpholinylcarbonyl) but-1-yloxy, 2- (4-rnorfolinylcarbonyl) but-1-yloxy, 3- (4-morpholinylcarbonyl) but-l-yloxy, 4-4- (4-morpholinylcarbonyl) but-l-yloxy, - (4-morpholinylcarbonyl) but-2-yloxy, 2- (4-morpholinylcarbonyl) but-2-yloxy, 1- (4-morpholinylcarbonyl) but-3-yloxy, 2- (4-morpholinylcarbonyl) but-3- Ioxy, 1- (4-morpholinylcarbonyl) -2-methylprop-3-yloxy, 2- (4-morpholinylcarbonyl) -2-methyl-prop-3-yloxy, 3- (4-morpholinylcarbonyl) -2-methyl-prop -3-yloxy or 2- (4-morpholinylcarbonylmethyl) -prop-2-yloxy. As regards the application of the compounds of Formula I or I ', respectively, according to the present invention, as variables of 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: R is hydrogen; R2 is CpC4-haloalkyl, especially trifluoromethyl; R3 is hydrogen; R is halogen, especially chlorine; R is hydrogen, fluorine or chlorine; R is hydrogen; R 7, R 8, R 9y, R 10 are hydrogen, fluorine, chlorine or methyl; R has all meanings, except hydrogen, cyano and halogen; Especially preferred are the compounds listed in the following Table 1 (* Ia with n = zero, R1, R3, R5 to R10, R12 and R13 = hydrogen, R = trifluoromethyl, R = chloro.) Table 1: ?? On the other hand, the following substituted 2-phenylpyridines of the Formula I are especially preferred: compounds Ib.001-Ib.202, which differ from the corresponding compounds Ia.001-Ia.202, only in the fact that R represents fluorine: - the compounds Ic.001-Ic.202, which differ from the corresponding compounds Ia.001-Ia.202, only in the fact that R9 represents methyl: - the compounds Id.001-Id.202, which differ from the corresponding compounds Ia.001-Ia.202, only in the fact that R represents fluorine and R represents methyl: - the compounds Ie.001-Ie.202, which differ from the corresponding compounds Ia.001-Ia.202, only in the fact that R represents chlorine: - compounds If.001-If.202, which differ from the corresponding compounds Ia.001-Ia.202, only in the fact that R represents fluorine and R9 represents chlorine: - the compounds Ig.001-Ib.202, which differ from the corresponding compounds Ia.001-Ia.202, only in the fact that R represents methyl: - the compounds Ih.001-Ih.202, which differ from the corresponding compounds Ia.001-Ia.202, only in the fact that R represents fluorine and R represents methyl: - the compounds Ii.001-Ii.202, which differ from the corresponding compounds Ia.001-Ia.202, only in the fact that Rreepprreesseennttaa cclloorroo :: - the compounds Ik.001-Ik.202, which differ from the corresponding compounds Ia.001-Ia.202, only in the fact that R5 represents fluorine and R represents chlorine: - the compounds Im.001-Im.202, which differ from the corresponding compounds Ia.001-Ia.202, only in the fact that R represents fluorine: The substituted 2-phenylpyridines of Formula I can be obtained in various ways, for example by following the following procedures: Method A: Reaction of the 2- (4-hydroxyphenyl) pyridines II with benzyl halides or mesylates, III, in a manner of if known. { see for example H. Meerwein in: Houben-Weyl, Methoden der Organischen Chemie, Volume VI / 3, Part 3, p. 54 and following, and: A.D. Batcho & W. Leingruber, Org. Synth 63, 214 (1984)} : L represents chlorine, bromine or methylsulfonyloxy. The development of the reaction preferably takes place in an inert aprotic solvent such as dimethyl formamide, dimethyl sulfoxide, acetonitrile and acetone. Depending on the substituents and corresponding reactive conditions, it may be advantageous to operate in the presence of a base in an approximately equivalent amount, referred to II. As bases, for example, alkali metal carbonates such as sodium hydrogencarbonate and sodium carbonate can be used, as well as nitrogenous bases such as pyridine and triethylamine. The reaction temperature is usually in the range of 0 to 100 ° C. The components are usually applied in a roughly stoichiometric ratio, but an excess of one of the components may be advantageous, for example in order to achieve the most complete reaction possible from the other component. Method Bt Reaction of the 2- (4-hydroxyphenyl) pyridines II with benzyl halides, IV, in a manner known per se (see for example H. Henecka in: Houben-Weyl, Methoden der Organischen Chemie, Volume VTÍI, Pág. 543 et seq., And: TS Wheeler, Org. Synth. Coll. IV 1963, page 478): Hai1 represents chlorine or bromine. As a suitable inert solvent, we have for example chlorinated aliphatic hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride and 1,2-dichloroethane. Depending on the substituents and corresponding reactive conditions, it may be advantageous to operate in the presence of a base. As for the bases, temperature of the reaction and relations between the quantities, the indications indicated for Procedure A) apply. Method C: Reaction of the 2- (4-hydroxyphenyl) pyridines II with substituted anhydrides of phthalic acid, IV, in a manner known per se. { see for example H. Henecka in: Houben-Weyl, Methoden der Organischen Chemie, Volume VIII, p. 547 et seq., And: P.C. Crofts and Other (s), in: Org. Prep. Procedure Int., 22 (4), 538-540 (1990)} : Suitable solvents are, for example, the hydrocarbons mentioned for Process B. Typically, the reaction temperature is from 0 to 100 ° C. The reaction components are usually applied in approximately stoichiometric amounts, but there is also the possibility of applying one of the components in excess. Procedure D; Oxidation of the 2-phenylpyridines of Formula I, in which 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), 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 62, 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 normally applied in an amount of at least equimolar, based on the starting composition. In some particular cases, it is possible that a greater excess of the oxidation agent is advantageous. Method E: Reaction of the 2-halogenopyridines VI with boric acids VII, boroxines VIII or, provided that the substituents R ia R 1"? Are inert under the conditions of the Grignard reaction, with Grignard IX compounds, in a manner in itself, in the presence of a base and a catalyst (see for example DE-a 43 23 916, and the technical literature therein indicated): Hai1 represents chlorine or bromine; Hai represents bromine or iodine. Generally, it is worked in an inert solvent (in the form of a mixture), for example in tetrahydrofuran / water, dioxane / water, dimethoxy / water, toluene / water, or in dimethylformamide. As catalysts, palladium and nickel compounds, such as tetrakis- (triphenylphosphine) -palladium (0), [1,2-bis- (diphenylphosphine) -ethan] -palladium (II) chloride, [1, -bis- (diphenylphosphino) -ferrocene] -palladium (II), palladium (II) acetate and bis (triphenylphosphine) nickel (II). They are applied in preferably catalytic amounts. Suitable bases are, for example, alkali metal carbonates such as sodium carbonate, alkali metal hydrogen carbonate such as sodium hydrogencarbonate, alkali metal hydroxides such as sodium hydroxide, alkali metal phosphates such as potassium phosphate, as also the alkylamines such as triethylamine. In general, the reaction is carried out at a temperature of 20 ° C at the boiling temperature of the reaction mixture. In general, the molar ratio between VI and the base is 1: 1 to 1: 5.
Usually, the starting compounds VI and VII, VIII or IX are applied in approximately equimolar amounts, but it is possible to apply one of the excess components. The 2-halopyridines VI are known or can be obtained in a manner known per se (see for example: D. Spitzner in Houben-Weyl: Methoden der Organischen Chemie, Volume E7b, 286 et seq.).
The boric acids VIII and the boroxines VIII have been disclosed in for example the following documents: DE-A 42 36 105, EP-A 569 193 or JP-A 05/025 158, or they can be prepared in a manner known per se (cfs for example MF Lappert, Chem. Rev. 56, 959 (1956); K. Torssell in: H. Steinberg and A.L. McCloskey (ED): Progress in Boron Chemistry, 1, 369 (1964) and R.Koestner in Houben-Weyl, Methoden der Organischen Chemie, Volume 13/3 a, 4a. Edition 1982, 617 et seq.). 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 compounds I that carry an amino group in terminal position, can form acid addition salts. The compounds I / 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 / 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, the Compounds I / I ', or the herbicidal agents that contain them, can also be used in another quantity of crop plants, to combat the 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 the compounds I / I 'in those crops that thanks to their selective reproduction and / or genetic technology methods have acquired a certain tolerance against the effect of the herbicides. On the other hand, the substituted 2-phenylpyridines I / 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, 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 good controllable defoliation (defoliation) of 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 / 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 dispersions or dispersions, in the form of emulsions, oil dispersions, pastes, dusts, sowing or granulating agents, by spraying, 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, aliphatic, cyclic and aromatic hydrocarbons, for example, paraffins, tetrahydronaphthalin, alkylated naphthalenes or derivatives thereof, alkylated benzoles and their derivatives, 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 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 between 0.01 and 90 percent by weight, of the active substance. Therefore, the active substances are applied with a purity of 90 percent to 100 percent, preferably 95 percent to 100 percent (measured by the NMR spectrum). The following formulation examples clarify the preparation of said preparations: I.- 20 parts by weight, of compound No. Ia.075 are dissolved in a mixture consisting of 80 parts by weight, of alkylated benzene, 10 parts by weight, of the product of the addition of 8 to 10 moles of ethylene oxide with 1 mole of N-monoethanolamide of acid 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. Ia.076 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.I.0.019 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 is obtained. % by weight of the active substance. IV.- 20 parts by weight of the active substance No.Ic.020 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 the form of powder, and ground in a hammer mill. By pouring and fine distribution of 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.It.201 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.Ia.071 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 la.141 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 compound la.146 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 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 / I ', depend on the objective of the struggle, of the season or season of the year, of the target plants and of 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 extend the spectrum of effectiveness and in order to achieve synergistic effects, it is possible to mix the substituted 2-phenylpyridines, I / I ', with numerous representatives of other groups of active substances such as herbicides or growth regulators, and apply them in a joint For example, as co-components of the mixture, 1,2,4-thiadiazole, 1,3,4-thiadiazole, amides, aminophosphoric acids and their derivatives, aminotriazoles, anuides, aryloxy acids / Lactate 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 its derivatives, ureas, 3-phenyluracils, imidazoles, imidazo linone, N-phenyl-3,4,5,6-tetrahydroftalimide, oxadiazole, phenols, esters of aryloxyphenoxypropionic acids, phenylacetic acids and their derivatives, 2-phenylpropi acids nicos and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl, sulfonamide, sulfonylurea, triazinones, uracils and xamidas triazolcarbo.
On the other hand, it may be useful to apply the compounds I 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: 3-cORO-2- (4- [4-methyl-2- (l-methyl-methoxycarbonylmetoxO-benzy-oxy] -phiD-5-trifluoromethyl-pyridine (No. Ic.019) CH (CH3) CO - OCH3 2.5 g of an 80% by weight suspension of sodium hydride in mineral oil were suspended in 30 ml of water-free dimethylformamide. To said suspension was added, dropwise within 30 minutes, a solution of 12.3 g of 3-chloro-2- (4-hydroxyphenyl) -5-trifluoromethylpyridine (disclosed in DE-A 43 23 916) in 150 ml of dimethylformamide free of water, after which it was stirred for an additional 10 minutes. In the reaction mixture, a solution of 12.1 g of 2- (2-chloromethyl-5-methyl-phenoxy) propionic acid methyl ester in 50 ml of dimethylformamide was added dropwise within 10 minutes. Water. It was then stirred for 8 hours at a temperature of 80 ° C, and for 24 hours at 23 ° C. The solvent was then removed predominantly, by evaporation. The residue was subjected to stirring in 1.5 liter of water, and the pharmaceutically acceptable was extracted three times with 200 ml of methyl-tert each time. butyl ether. After washing the combined organic phases with 100 ml of water, dried over sodium sulfate, and recovered. Purification of the crude product was carried out by silica gel chromatography, eluting with cyclohexane / ethyl acetate (4: 1). Yield: 11.1 g (52%) of white crystals. Melting point: 117 - 119 ° C. ^ -NMR (270 MHz, in CDC13): "5 [ppm] = 1.65 (d, 3H), 2.33 (s, 3H), 3.76 (s, 3H), 4.85 (q, 1H), 5.20 (d, 1H), 5.30 (d, lH), 6.60 (s, lH), 6.83 (d, lH), 7.13 (d, 2H), 7, 35 (d, lH), 7.77 (d, 2H), 8.00 (s, lH), 8.82 (s, lH). Table I and the following Tables 2 and 3 show other compounds I according to the present invention, and also compounds I ', which were prepared in the same manner or which can be prepared in the same manner: Table 2 (2) in CDC13 (3) in d -dimethylsulfoxide 'Table 3 Application Examples (Herbicidal efficacy) The herbicidal efficacy of the substituted 2-phenylpyridines I / I 'could be demonstrated by the following greenhouse tests: Flower pots, made of plastic material, provided with silty sand, were used as culture vessels. approximately 3 percent humus, as a substrate. The seeds of the various test plants were seeded separately according to their species. For the pre-emergence treatment, the active substances, suspended or emulsified in water, were applied directly after sowing, by means of very fine distribution nozzles or showers. 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 active substances suspended 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 0.125 or 0.0625 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 ° G, 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-emergence treatment in an amount of 0.125 or 0625 kg of active substance per hectare, Compound No. Ia.019 showed a very good effect against the plants just indicated. Application Example (Effectiveness as a dissector / defoamer) As young plants under test, young 4-leaf cotton plants (without germination leaves), which had been grown under greenhouse conditions (relative ambient humidity: 50 to 70%, day / 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 fatty alcohol alkoxylate 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 defoliation (defoliation) was determined mathematically, in percentage. In the control plants, which did not receive treatment, leaf fall was not observed.

Claims (16)

  1. R E I V I N D I C A C I O N E 1.- 2-substituted phenylpyridines, characterized in that they correspond to the following general formula (I): in which the variables have the following meanings: n = 0 or l; R, R, R independently of each other, represent: hydrogen, halogen, C 1 -C 4 -alkyl, C j -C 4 -alkyl, hydroxy,
  2. Cj-C ^ alkoxy, Cj-C ^ halogenoalkoxy, nitro, amino, Cj-C ^ alkylamino, dHCj-C ^ alkyl) amino, mercapto, Cj-C ^ alkylthio, C ^ -C ^ haloalkyl, cyano, hydroxycarbonyl, (C? -C4-alkoxy) carbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, or di- (CyC4-alkyl) aminocarbonyl; R = hydrogen, halogen, C1-C4-alkyl, Cj-C4-halogen alkyl, cyano, nitro, amino, hydroxy, Cj-C ^ halogen alkoxy, mercapto, Cj-C4-alkylthio, Cj-C-haloalkylthio, C] -C 4 -alkylsulfinyl, C C 4 -haloalkylsulfinyl, Cj-C 4 -alkylsulfonyl, or Cj-C 4 -haloalkylsulfonyl; R = hydrogen, cyano or halogen;
  3. R and R independently from each other represent hydrogen or halogen; X = methylene or carbonyl; R7, R8, R9, R10, independently of one another, represent: hydrogen, nitro, cyano, halogen, Cj-C ^ -alkyl, C1-C4-halogenoalkyl, C ^ ^ -alkoxy or C1-C4-halogen alkoxy; R = hydrogen, halogen, Cj-C ^ alkyl, Cj-C ^ halogen alkyl; C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, hydroxycarbonyl-C 1 -C 4 -alkyl, hydroxycarbonyl-C 2- C4-to quenyl, hydroxycarbonyl-C2-C4-alkynyl, (C4-alkoxy) carbonyl-CJ-C4-alkyl, (C4-alkoxy) carbonyl-C2-C4-alkenyl, (Cj-C ^ alkoxy) carbonyl -C2-C4-alkynyl, (C1-C4-alkoxy) carbonyl-C2-C4-halogenoalkyl, (Cj-1 ^ -alkoxy) carbonyl-C2-C4-haloalkenyl, aminocarbonyl-C-C4-alkyl, aminocarbonyl- C2-C4-alkenyl, aminocarbonyl-C2-C4-alkynyl, C1-C4-alkylaminocarbonyl-C-C4-alkyl, alkenyl, Cj-C ^ alkylamino-C2-C4-alkynyl, di- (Cj-C4-alkyl) ) -aminocarbonyl-C-C4-alkyl, di- (C j -C4) -aminocarbonyl-C2-C4-alkenyl, di (Cj-C4-alkyl) aminocarbonyl-C2-C4-alkynyl, amino-C-carbonyl C4-haloalkyl, aminocarbonyl-C2-C4-halogen alkenyl, Cj-C4-alkylaminocarbonyl-Cj-C4-halogen alkyl, C j -C4-alkylaminocarbonyl-C2-C-halogeno alkenyl, di- (C- C4-alkyl) aminocarbonyl-C2-C4-halo alkyl, di- (Cj-C4-alkyl) aminocarbonyl-C2-C4-halogen alkenyl, (hydroxycarbonyl-Cj-C4-alkyl) -aminocarbonyl-C2-C4-alkenyl, (hydroxycarbonyl-C j -C4-alkyl) aminocarbonyl -C2-C4-haloalkenyl, N- (hydroxy carbonyl-C1-C4-alkyl) -N- (C1-C4-alkyl) -amino carbonyl-C2-C4-alkenyl, N- (hydroxy carbonyl-C j -C4- alkyl) -N- (C -C4-alkyl) aminocarbonyl-C2-C4-halogen alkenyl, [(Cj-C4-alkoxy) carbonyl-Cj-C4-alkyl] -amino carbonyl-C2-C4-alkenyl, [(C C4-alkoxy) carbonyl-C j -C4-alkyl] -aminocarbonyl-C2-C4-haloalkenyl, N - [(C j -C4-alkoxy) carbonyl-C1-C4-alkyl] -N- (C | - C4-alkyl) -amino carbonyl-C2-C4-alkenyl, N - [(C j -C4-alkoxy) carbonyl-C-C4-alkyl] -N- (C j -C4-alkyl) amino-carbonyl-C2- C4-halogen alkenyl, 2 - [(C1-C4-alkoxy) carbonyl] -pyrrolidin-1-yl-carbonyl-C2-C4-alkenyl, 2 - [(C1-C4-alkoxy) carbonyl] -pyrrolidin-1-yl -carbonyl-C2-C4-halogen alkenyl, formyl, (Cj-C4-alkyl) carbonyl, (C j -C4-haloalkyl) carbonyl, hydroxyimino-C ^ -4-alkyl, C j -C4-alkoxy no-C j -C 4 -alkyl, 1, 1 -di (C 4 -C 4) -C 4 -C 4 -alkyl, nitro, hydroxyamino, amino, C 1 -C 4 -alkylamino, C 3 -C 4 -cycloalkylamino, di ( C1-C4-alkyl) amino, (C4-alkyl) carbonylamino, (C1-C4-haloalkyl) carbonylamino, C1-C-alkylsulfonylamino, di (Cj-C4-alkyl sulfonyl) amino, C1-C4-halogenoalkylsulfonyl amino, hydroxy , C1-C4-alkoxy, Cj-C4-haloalkoxy, cyano-C1-C4-alkoxy, C ^ -alkoxy-Cj-C ^ alkoxy, C4 C4-alkylthio-Cj-C4-alkoxy, C2-C4-alkynyloxy, hydroxycarbonyl , Cj-C ^ alkoxy, (Cj-C6-alkoxy) carbonyl-C j -C 4 -alkoxy, C-C 4 -alkyl- (C j -C 4 -alkoxy) carbonyl-C j -C 4 -alkoxy, (C j -C 4 -alkoxy) carbonyl- (C j -C 4 -alkoxy) carbonyl-C j -C 4 -alkoxy, aminocarbonyl-C j -C 4 -alkoxy, C-C 4 -alkylaminocarboyl-C j -C 4 -alkoxy. di (Cj-C4-alkyl) amino carbonyl-C j-C ^ alkoxy, 1-pyrrolidinyl-carbonyl-C1-C4-alkoxy, 1-piperidi-nyl-carbonyl-C-C-alkoxy, 4-morpholinyl-carbon-n-C1-C4-alkoxy, aminocarbonyl- (C1-C4-alkoxy) -carbonyl- CpC ^ alkoxy, (C1-C-alkyl) aminocarbonyl- (Cj-C4-alkoxy) carbonyl-C 1 -C 4 -alkoxy, di (C 1 -C 4 -alkyl) aminocarbonyl- (C 1 -C 4 -alkoxy) carbonyl-C1 -C4-alkoxy, 1- pyrro lidiyl carboniKC C ^ alkoxy) carbonyl-C ^ -4-alkoxy, 4-morpholinylcarbonyl- (C-C4-alkoxy) carbonyl-Cj-C4-alkoxy, [(C1-C4-alkoxy) carbonyl-C1-C4-alkyl] amino carbonyl-C! -C 4 -alkoxy, N - [(C 1 -C 4 -alkoxy) carbonyl-C j -C 4 -alkyl] -N- (C j -C 4 -alkyl) amino carbonyl-C j-C 4 -alkoxy, [2- [ (C1-C4-alkoxy) carbonyl] -pyrolidin-l-yl] carbonyl-Cj-C4-alkoxy, cyano, hydroxy carbonyl, COC, (C1-C4-alkoxy) carbonyl, (C1-C4-halogeno alkoxy) carbonyl, Cj-C4- carbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, di- (C j -C4-alkyl) -aminocarbonyl, C3-C6-cycloalkyl aminocarbonyl, 1-pyrrolidinylcarbonyl, 1-piperhexylcarbonyl, 4-morpho linylcarbonyl, hydroxycarbonyl-C and ^ -alkylaminocarbonyl, N- (hydroxycarbonyl-C 1 -C 4 -alkyl) -N- (C 1 -C -alkyl) -aminocarbonyl, (Cy C 4 -alkoxy) carbonyl-C 1 -C 4 -alkyl amino carbonyl, N - [(Cj-C4-alkoxy) carbonyl-C1-C4-alkyl] -N- (C1-C4-alkyl) -aminocarbonyl, 2-hydroxy carbonyl pyrrolidin-1-yl-carbonyl, 2 - [( C1-C4-alkoxy) carbonyl] -pyrrolidin-1-yl-carbonyl, or a group:
  4. R14
  5. And Z in which Formula: Y and Z, independently of each other, represent oxygen or sulfur;
  6. R14 represents hydrogen, C1-C4-alkyloxy (C1-C4-alkoxy) carbonyl, and Alk represents an ethylenic or trimethylenic chain, in which one or more hydrogen atoms can be replaced individually by Cj-j-alkyl or (Cj- C4-alkoxycarbonyl; R1 - hydrogen, nitro, amino, hydroxylamino, C1-C4-alkylsulfoni-lamino, di- (C j -C -alkylsulfonyl) amino, C-C4-halogenoalkylsulfonylamino, (C 1 -C 4 -alkoxy) carbonyl-C 1 -C 4- haloalkyl or (C4-C4-alkoxy) arbonyl-C2-C4-halogenalkenyl; with the proviso that R5,
  7. R 7 ', R 1 1, and R 11' Jí, they can not all simultaneously represent hydrogen, or that R7 and R, or R10 and R1 1, can not simultaneously represent fluorine, as well as the salts usable in agriculture, of the compounds I, insofar as they exist. 2. Substituted 2-phenylpyridines of Formula I according to claim 1. characterized in that R1I and RJ "represent hydrogen, R2 represent Cl-C4-haloalkyl and R represents halogen." 3.- Use of the substituted 2-phenylpyridines. of Formula I 'and salts of I' usable in agriculture, I 'corresponding to the definition of I according to claim 1, but without the proviso, as herbicides or for the dissection and / or defoliation of 4.- Herbicidal composition, characterized in that it contains an herbicidally effective amount, of at least one substituted 2-phenylpyridine of Formula I, or of a salt of I used in agriculture, in accordance with claim 1, and at least one inert material, liquid and / or solid, and optionally also at least one surface-active material 5.- Composition for the desiccation and / or defoliation of the plants, in accordance with n claim 4, characterized in that it contains an amount effective from the point of view of dissectant and / or defoliant, of at least one substituted 2-phenylpyridine of Formula I, or of a salt of I used in agriculture, in accordance with 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 agents as herbicides, according to claim 1-4, characterized in that an herbicidally effective amount of at least one substituted 2-phenylpyridine of the Formula is mixed together. I, or of an I salt usable in agriculture, according to claim 1, and with at least one inert, liquid and / or solid carrier material, and optionally also with at least one surface-active material. 7. Process for the preparation of effective agents as desiccants and / or defoliants, according to claim 5, characterized in that an amount effective from the dissecting and / or defoliant point of view of at least one of them is mixed with one another. substituted 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 at least one surface-active material.
  8. 8. Process for combating 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', is allowed to act. useable in agriculture, I 'corresponding to the definition of I according to claim 1, but without the proviso, on the plants, on the living space thereof, 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 is allowed to act., or of a salt of I 'usable in agriculture, I' corresponding to the definition of I according to claim 1, but without the proviso, on the 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 substituted 2-phenyl pyridines of Formula I according to claim 1, in which X represents methylene, characterized in that it is reacted in a known manner in a solvent or diluent, inert, optionally in the presence of a base, a 2- (4-hydroxyphenyl) pyridine of Formula II: wherein the variables have the meanings given in claim 1, with a halide or benzyl mesylate of Formula III: wherein L represents chloro, bromo or methylsulphonyloxy.
  12. 12. Process for the preparation of substituted 2-phenyl pyridines of Formula I according to claim 1, in which X represents carbonyl, characterized in that it is reacted in a known manner in a solvent or diluent, inert, optionally in the presence of a base, a 2- (4-hydroxyphenyl) pyridine of Formula II: with a benzyl halide of Formula IV: in which Hai i1 represents chlorine or bromine.
  13. 13. - Process for the preparation of substituted 2-phenyl pyridines of Formula I according to claim 1, in which X represents carbonyl and R represents hydroxycarbonyl, characterized in that it is reacted in a known manner in a solvent or diluent, inert, a 2- (4-hydroxyphenyl) pyridine of Formula II: wherein the variables have the meanings indicated in claim 1, with a substituted phthalic acid anhydride, of Formula V:
  14. 14. - Process for the preparation of substituted 2-phenyl pyridines of Formula I according to claim 1, in which n is 1, characterized in that the corresponding 2-phenylpyridine is oxidized in which n represents zero, in a manner in itself known.
  15. 15. Use of 2- (4-hydroxyphenyl) pyridines of Formula II, in which the variables have the meaning indicated in claim 1, for the preparation of the substituted 2-phenylpyridines of Formula I in accordance with claim 1.
  16. 16. Process for the preparation of substituted 2-phenylpyridines of Formula I according to claim 1, characterized in that 2-halogeno-pyridine of Formula VI is reacted: wherein R a R and the index have the meanings indicated in claim 1 and Hai represents chlorine or bromine, in a manner known per se in a solvent or diluent, inert, in the presence of a base and a palladium catalyst or nickel, with a boric acid of Formula VII: or with a boroxine of Formula VIII: or, as long as the substituents R to R 3 are inert under the conditions of the Grignard reaction, with a Gtignard compound of the Formula IX: wherein in each case X and R to R have the meanings indicated in claim 1, and Hai represents bromine or iodine. 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, alkylthio, haloalkylthio, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl; R2 = H, OH, SH, N02, NH2, CN, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkyl sulfinyl, alkylsulfonyl, haloalkylsulfonyl; R5 = H, CN, halogen; R6, R13 = H, halogen; X = -CH-, -CO-; R R77, RR88, RR99, RR1100 = H, N02, CN, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy; Ru = H, OH, N02, NH2 NHOH, CN, CHO, COOH, COCÍ, CONH2, 1- pyrrolidinylcarbonyl, 1-piperidinylcarbonyl, 4-morpholinylcarbonyl, 2-hydroxycarbonyl-pyrrilidin-1-yl-carbonyl, halogen or various organic radicals; R 12 = H, N 0 2, NH 2, NHOH, alkylsulfonylamino, dialkyl sulfonyl amino, halogenoalkylsulfonylamino, alkoxycarbonyl halogen alkyl, alkoxycarbonylhalogen alkenyl; as well as its salts, with the exception of those I, in which R, R, R, R, represent, all of them, hydrogen, be R and R or R, represent fluorine. Application: as a herbicide; for the dissection / defoliation of plants.
MXPA/A/1997/004926A 1995-01-13 1997-06-30 2-substitute phenilpiridines, procedure parasu obtaining and the herbicidal compositions that contain them MXPA97004926A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19500760.3 1995-01-13
DE19500760A DE19500760A1 (en) 1995-01-13 1995-01-13 Substituted 2-phenylpyridines
PCT/EP1996/000022 WO1996021647A1 (en) 1995-01-13 1996-01-04 Substituted 2-phenylpyridines as herbicides

Publications (2)

Publication Number Publication Date
MX9704926A MX9704926A (en) 1997-10-31
MXPA97004926A true MXPA97004926A (en) 1998-07-03

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