Selective herbicidal compositions and methods for controlling of undesired plants in tame cultures

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to selective herbicidal compositions, containing customary auxiliary substances, as well as: a) herbicidal effective amount of compound of formula I or agriculture acceptable salt thereof wherein R are independently C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alcoxy-C1-C4-alkyl, or C1-C4-alcoxy-C1-C4-alcoxy-C1-C4-alkyl; m = 2; Q is group of formula wherein R23 is hydroxyl and Y is C1-C4-alkylen bridge; and b) synergetically effective amount of one or more herbicides; and methods for controlling of undesired plants in tame cultures using the said composition. Also disclosed is composition containing customary auxiliary substances, as well as herbicidal and synergetically effective amount of 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one of formula 2.2 and herbicidal antagonistically effective amount of antidote of formula 3.1. Compositions based on 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one and herbicidal antagonistically effective amount of antidote, as well as methods for controlling of weeds and cereal grasses in tame cultures also are described.

EFFECT: compositions useful in effective controlling of many weeds both in pre-spring and post-spring phases.

5 cl, 63 tbl, 12 ex

 

The present invention relates to a new herbicide compositions containing a combination of herbicide active ingredients and is suitable for selective weed control in crops of useful plants, such as corn. The invention relates also to a method of combating weeds in crops of useful plants, as well as the application of this new compositions for this purpose.

The compounds of formula I

in which the substituents have the following values have herbicide activity.

With the invention it has been unexpectedly found that the combination used in a variety of quantities of active ingredients, i.e. the combination of the active ingredient of formula I with one or more below the active ingredients of formulae 2.1 to 2.51, which are known compounds and some are commercially available products, exhibits a synergistic effect that allows the use of such combination for effective control of most weeds, occurring primarily in crops of useful plants, both at pre-and post-harvest stage.

In accordance with this invention proposes a new synergistic effect of the composition for the selective combating of weeds is mi, which in addition is usually used in cooking techniques preparative forms inert auxiliary substances (adjuvants) contains as active ingredient a mixture of

a) herbicide effective amount of the compounds of formula I

in which

R in each case independently denotes hydrogen, C1-C6alkyl, C2-C6alkenyl,2-C6haloalkyl,2-C6quinil,2-C6haloalkyl,3-C6cycloalkyl, C1-C6alkoxygroup, C1-C6haloalkoxy, C1-C6allylthiourea, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, C1-C6haloalkyl,1-C6haloalkylthio,1-C6haloalkaliphilic,1-C6haloalkaliphilic,1-C6alkoxycarbonyl,1-C6alkylsulphonyl, C1-C6alkylamino, di(C1-C6alkyl)amino group, a C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminosulfonyl, -N(R1)-S-R2, -N(R3)SO-R4, -N(R5)-SO2-R6the nitrogroup, cyano, halogen, a hydroxy-group, amino group, menzilcioglu, benzylmorphine, bansilalpet, phenyl, fenoxaprop, phenylthiourea, phenylsulfinyl or dryer is sulfonyl, this phenyl group may be, in turn, mono-, di - or tizamidine C1-C6the alkyl, C1-C6haloalkyl,3-C6alkenyl,3-C6haloalkyl,3-C6the quinil,3-C6haloalkyl, C1-C6alkoxygroup, C1-C6haloalkoxy,3-C6alkenylacyl,3-C6alkynylamino, mercaptopropyl,1-C6alkylthiol,1-C6haloalkylthio,3-C6alkenylsilanes,3-C6haloalkylthio,3-C6alkylalcohol,2-C5alkoxyalkanols,3-C5acetylacetonato,3-C6alkoxycarbonylmethyl,2-C4cyanoacetylurea, C1-C6alkylsulfonyl,1-C6haloalkylthio,1-C6alkylsulfonyl,1-C6haloalkylthio, aminosulfonyl,1-C2alkylaminocarbonyl,2-C4dialkylaminoalkyl, group C1-C3alkylen-R45group NR46R47, a halogen, a cyano, a nitro-group, a phenyl or menzilcioglu, with the latter two groups that are phenyl group and menzilcioglu, in turn, can be for the emeny phenyl ring C 1-C3the alkyl, C1-C3haloalkyl, C1-C3alkoxygroup, C1-C3haloalkoxy, halogen, cyano or nitro-group, or

R in each case independently denotes monocyclic or condensed bicyclic ring system with 5 to 10 members, which may be aromatic or partially saturated and can contain 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, this ring system either directly attached to the pyridine ring, or attached to the pyridine ring through With1-C4alkylenes group, and each ring system may not contain more than two oxygen atoms and cannot contain more than two sulfur atoms, and the said ring system may be, in turn, mono-, di - or tizamidine C1-C6the alkyl, C1-C6haloalkyl,3-C6alkenyl,3-C6haloalkyl,3-C6the quinil,3-C6haloalkyl, C1-C6alkoxygroup, C1-C6haloalkoxy,3-C6alkenylacyl,3-C6alkynylamino, mercaptopropyl, C1-C6alkylthiol, C1-C6haloalkylthio,3-C6alkenylsilanes,3-C6haloalkylthio is Oh, With3-C6alkylalcohol,2-C5alkoxyalkanols,3-C5acetylacetonato,3-C6alkoxycarbonylmethyl,2-C4cyanoacetylurea,1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6alkylsulfonyl,1-C6haloalkylthio, aminosulfonyl,1-C2alkylaminocarbonyl,2-C4dialkylaminoalkyl, group C1-C3alkylen-R7group NR8R9, a halogen, a cyano, a nitro-group, a phenyl or menzilcioglu, and phenyl and menzilcioglu, in turn, can be substituted in the phenyl ring C1-C3the alkyl, C1-C3haloalkyl, C1-C3alkoxygroup, C1-C3haloalkoxy, halogen, cyano or nitro-group, while the substituents at the nitrogen atom in the heterocyclic ring are different from halogen, or

R in each case independently means1-C4alkoxy-C1-C4alkyl or C1-C4alkoxy-C1-C4alkoxy-C1-C4alkyl,

m denotes 1, 2, 3,or 4

R1, R3and R5each independently of one another denotes hydrogen or C1-C6alkyl,

R2mean NR10R11C 1-C6alkoxygroup, C1-C6haloalkoxy, C1-C6alkyl, C1-C6haloalkyl,3-C6alkenyl,3-C6haloalkyl,3-C6quinil,3-C6haloalkyl,3-C6cycloalkyl or phenyl, and the phenyl may be, in turn, substituted C1-C3the alkyl, C1-C3haloalkyl, C1-C3alkoxygroup, C1-C3haloalkoxy, halogen, cyano or nitro-group,

R4mean NR12R13C1-C6alkoxygroup, C1-C6haloalkoxy, C1-C6alkyl, C1-C6haloalkyl,3-C6alkenyl,3-C6haloalkyl,3-C6quinil,3-C6haloalkyl,3-C6cycloalkyl or phenyl, and the phenyl may be, in turn, substituted C1-C3the alkyl, C1-C3haloalkyl, C1-C3alkoxygroup, C1-C3haloalkoxy, halogen, cyano or nitro-group,

R6mean NR14R15C1-C6alkoxygroup, C1-C6haloalkoxy, C1-C6alkyl, C1-C6haloalkyl,3-C6alkenyl,3-C6haloalkyl,3-C6quinil,3-C6galaal the Nile, With3-C6cycloalkyl or phenyl, and the phenyl may be, in turn, substituted C1-C3the alkyl, C1-C3haloalkyl, C1-C3alkoxygroup, C1-C3haloalkoxy, halogen, cyano or nitro-group,

R7and R45each independently from each other mean C1-C3alkoxygroup,2-C4alkoxycarbonyl, C1-C3allylthiourea, C1-C3alkylsulfonyl, C1-C3alkylsulfonyl or phenyl, and the phenyl may be, in turn, substituted C1-C3the alkyl, C1-C3haloalkyl, C1-C3alkoxygroup, C1-C3haloalkoxy, halogen, cyano or nitro-group,

R8, R10, R12, R14and R46each independently of one another denotes hydrogen or C1-C6alkyl,

R9, R11, R13, R15and R47each independently from each other mean C1-C6alkyl or C1-C6alkoxygroup,

Q means a group of Q1

in which

R16, R17, R18and R19each independently from each other mean a hydrogen, a hydroxy-group, With1-C4alkyl, C2-C6alkenyl,2-C6quinil,1-C4alkoxy ronil, C1-C6allylthiourea, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl group1-C4alkyl-NHS(O)2With1-C4haloalkyl, -NH-C1-C4alkyl, -N(C1-C4alkyl)2C1-C6alkoxygroup, a cyano, a nitro-group, halogen or phenyl, which may be in turn substituted With1-C4the alkyl, C1-C4haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,1-C4alkylcarboxylic,1-C4alkoxycarbonyl, amino group, With1-C4alkylaminocarbonyl, di(C1-C4alkyl)amino group, With1-C6alkylthiol, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, group C1-C4alkyl-S(O)2O1-C4haloalkylthio,1-C4haloalkylthio,1-C4haloalkylthio, group C1-C4haloalkyl-S(O)2O group C1-C4alkyl-S(O)2NH1-C4alkyl-S(O)2N(C1-C4by alkyl), halogen, a nitro-group, a group COOH or by cyano, or two adjacent substituent from among R16, R17, R18and R19form2-C6Allenby bridge,

R20means a hydroxy-group, O-M +, halogen, C1-C12alkoxygroup,1-C12alkylcarboxylic,2-C4alkenylboronic,3-C6cycloalkylcarbonyl,1-C12alkoxycarbonylmethyl,1-C12alkylcarboxylic, R21R22N-C(O)O1-C12allylthiourea,1-C12alkylsulfonyl,1-C12alkylsulfonyl, C1-C4haloalkylthio,1-C4haloalkaliphilic, C1-C4haloalkaliphilic,2-C12altertekhnogrupp,2-C12alkanesulfonyl,2-C12alkanesulfonyl,2-C12haloalkylthio,2-C12haloalkaliphilic,2-C12haloalkaliphilic,2-C12alinytjara,2-C12alkylsulfonyl,2-C12alkylsulfonyl,1-C4alkyl-S(O)2O, phenyl-S(O)2O, (C1-C4alkoxy)2P(O)O1-C4alkyl(C1-C4alkoxy)P(O)O, N(C1-C4alkoxy)P(O)O, C2-C12-alkyl-S(CO)O, benzyloxy, fenoxaprop, phenylthiourea, phenylsulfinyl or phenylsulfonyl, with the phenyl group can be in turn substituted With1-C4the alkyl, C1-C4haloalkyl,1-C4alkoxy what Ruppel, With1-C4haloalkoxy,1-C4alkylcarboxylic,1-C4alkoxycarbonyl,1-C4alkylaminocarbonyl, di(C1-C4alkyl)amino group, With1-C4alkylthiol,1-C4alkylsulfonyl,1-C4alkylsulfonyl, group C1-C4alkyl-S(O)2O1-C4haloalkylthio,1-C4haloalkylthio,1-C4haloalkylthio, group C1-C4haloalkyl-S(O)2O group C1-C4alkyl-S(O)2NH1-C4alkyl-S(O)2N(C1-C4by alkyl), halogen, a nitro-group, or cyano, and

R21and R22each independently of one another denotes hydrogen or C1-C4alkyl,

or group of Q2

in which

R23means a hydroxy-group, O-M+, halogen, C1-C12alkoxygroup,1-C12alkylcarboxylic,2-C4alkenylboronic,3-C6cycloalkylcarbonyl, C1-C12alkoxycarbonylmethyl,1-C12alkylcarboxylic, R24R25N-C(O)O1-C12allylthiourea,1-C12alkylsulfonyl,1-C12alkylsulfonyl, C1-C 4haloalkylthio,1-C4haloalkaliphilic,1-C4haloalkaliphilic,2-C12altertekhnogrupp,2-C12alkanesulfonyl,2-C12alkanesulfonyl,2-C12haloalkylthio,2-C12haloalkaliphilic,2-C12haloalkaliphilic,2-C12alinytjara,2-C12alkylsulfonyl,2-C12alkylsulfonyl,1-C4alkyl-S(O)2O, phenyl-S(O)2O, (C1-C4alkoxy)2P(O)O1-C4alkyl(C1-C4alkoxy)P(O)O, N(C1-C4alkoxy)P(O)O, C1-C12-alkyl-S(CO)O, benzyloxy, fenoxaprop, phenylthiourea, phenylsulfinyl or phenylsulfonyl, with the phenyl group can be in turn substituted With1-C4the alkyl, C1-C4haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,1-C4alkylcarboxylic,1-C4alkoxycarbonyl,1-C4alkylaminocarbonyl, di(C1-C4alkyl)amino group, With1-C4alkylthiol,1-C4alkylsulfonyl,1-C4alkylsulfonyl, group C1-C4alkyl-S(O)2O1-C4haloalkylthio,1-C4haloalkyl what livinroom, With1-C4haloalkylthio, group C1-C4haloalkyl-S(O)2O group C1-C4alkyl-S(O)2NH1-C4alkyl-S(O)2N(C1-C4by alkyl), halogen, the nitro-group or a cyano,

R24and R25each independently of one another denotes hydrogen or C1-C4alkyl and

Y represents oxygen, sulfur, a chemical bond or a C1-C4Allenby bridge,

or group of Q3

in which

R44, R37, R38and R39each independently of one another denotes hydrogen, C1-C6alkyl, C1-C6haloalkyl,2-C6alkenyl,2-C6quinil, C1-C6alkoxycarbonyl, C1-C6allylthiourea, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, C1-C6alkyl-NHS(O)2C1-C6alkylamino, di(C1-C6alkyl)amino group, a hydroxy-group, C1-C6alkoxygroup,3-C6alkenylacyl,3-C6alkyloxy, hydroxy-C1-C6alkyl, C1-C4alkylsulfonate-C1-C6alkyl, tosyloxy-C1-C6alkyl, halogen, cyano, a nitro-group, phenyl or phenyl substituted With1-C4the alkyl, C1-sub> 4haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,1-C4alkylcarboxylic,1-C4alkoxycarbonyl, amino group, With1-C4alkylaminocarbonyl, di(C1-C4alkyl)amino group, With1-C6alkylthiol, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, group C1-C4alkyl-S(O)2O, C1-C6haloalkylthio, C1-C6haloalkylthio, C1-C6haloalkylthio, group C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH1-C6alkylthio-N(C1-C4by alkyl), C1-C6alkylsulfonyl-N(C1-C4by alkyl), C1-C6alkylsulfonyl-N(C1-C4by alkyl), halogen, a nitro-group, a group COOH or by cyano, or adjacent substituents R44and R37or R38and R39together represent a3-C6alkylen,

W stands for oxygen, sulfur, sulfinil, sulfonyl, -CR41R42-, -C(O) -, or-NR43-,

R41means hydrogen, C1-C4alkyl, C1-C4haloalkyl,1-C4alkoxy-C1-C4alkyl, C1-C4alkylthio-C1-C4alkyl, C1-C4alkylcarboxylic-C1-C alkyl, C1-C4alkylsulfonate-C1-C4alkyl, tosyloxy-C1-C4alkyl, di(C1-C3alkoxyalkyl)methyl, di(C1-C3alkylthiomethyl)methyl, (C1-C3alkoxyalkyl)-(C1-C3alkylthiomethyl)methyl, C3-C5oxocyclohexyl,3-C5talklounge,3-C4dioxocyclohexa,3-C4directlly,3-C4oxadiazolyl, formyl, C1-C4alkoxycarbonyl or phenyl, which may be in turn substituted With1-C4the alkyl, C1-C4haloalkyl, C1-C4alkoxygroup,1-C4haloalkoxy,1-C4alkylcarboxylic,1-C4alkoxycarbonyl, amino group, With1-C4alkylaminocarbonyl, di(C1-C4alkyl)amino group, With1-C4alkylthiol,1-C4alkylsulfonyl,1-C4alkylsulfonyl, group C1-C4alkyl-S(O)2O1-C4haloalkylthio,1-C4haloalkylthio,1-C4haloalkylthio, group C1-C4haloalkyl-S(O)2O group C1-C4alkyl-S(O)2NH1-C6alkylthio-N(C1-C4by alkyl), C1-C6alkylsulfonyl-N(C1-C4alkyl is m), C1-C6alkylsulfonyl-N(C1-C4by alkyl), halogen, a nitro-group, a group COOH or by cyano, or R42together with R39form C1-C6alkylen,

R42means hydrogen, C1-C4alkyl or C1-C4haloalkyl,

R40means a hydroxy-group, O-M+, halogen, C1-C12alkoxygroup,1-C12alkylcarboxylic,2-C4alkenylboronic,3-C6cycloalkylcarbonyl,1-C12alkoxycarbonylmethyl,1-C12alkylcarboxylic, R96R97N-C(O)O1-C12allylthiourea,1-C12alkylsulfonyl,1-C12alkylsulfonyl, C1-C4haloalkylthio,1-C4haloalkaliphilic,1-C4haloalkaliphilic,1-C12altertekhnogrupp,1-C12alkanesulfonyl,2-C12alkanesulfonyl,2-C12haloalkylthio,2-C12haloalkaliphilic,2-C12haloalkaliphilic,2-C12alinytjara,2-C12alkylsulfonyl,2-C12alkylsulfonyl,1-C4alkyl-S(O)2O, phenyl-S(O)2O, (C1-C4alkoxy)2P(O)O1-C4al is Il(C 1-C4alkoxy)P(O)O, N(C1-C4alkoxy)P(O)O1-C12alkyl-S(CO)O, benzyloxy, fenoxaprop, phenylthiourea, phenylsulfinyl or phenylsulfonyl, with the phenyl group can be in turn substituted With1-C4the alkyl, C1-C4haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,1-C4alkylcarboxylic,1-C4alkoxycarbonyl,1-C4alkylaminocarbonyl, di(C1-C4alkyl)amino group, With1-C4alkylthiol,1-C4alkylsulfonyl,1-C4alkylsulfonyl, group C1-C4alkyl-S(O)2O1-C4haloalkylthio,1-C4haloalkylthio,1-C4haloalkylthio, group C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH1-C4alkyl-S(O)2N(C1-C4by alkyl), halogen, the nitro-group or a cyano,

R96and R97each independently of one another denotes hydrogen or C1-C4alkyl,

R43means hydrogen, C1-C4alkyl, C1-C4alkoxycarbonyl or phenyl, which may be in turn substituted With1-C4the alkyl, C1-C4haloalkyl,1-C4 alkoxygroup,1-C4haloalkoxy,1-C4alkylcarboxylic,1-C4alkoxycarbonyl,1-C4alkylaminocarbonyl, di(C1-C4alkyl)amino group, With1-C4alkylthiol,1-C4alkylsulfonyl,1-C4alkylsulfonyl, group C1-C4alkyl-S(O)2O1-C4haloalkylthio,1-C4haloalkylthio,1-C4haloalkylthio, group C1-C4haloalkyl-S(O)2O group C1-C4alkyl-S(O)2NH1-C4alkyl-S(O)2N(C1-C4by alkyl), halogen, the nitro-group or a cyano, or a group Q4

in which

R30means a hydroxy-group, O-M+, halogen, C1-C12alkoxygroup,1-C12alkylcarboxylic,2-C4alkenylboronic,3-C6cycloalkylcarbonyl,1-C12alkoxycarbonylmethyl,1-C12alkylcarboxylic, R31R32N-C(O)O1-C12allylthiourea,1-C12alkylsulfonyl,1-C12alkylsulfonyl, C1-C4haloalkylthio,1-C4haloalkaliphilic,1-C4Halaal sulfonyl, With1-C12altertekhnogrupp,1-C12alkanesulfonyl,2-C12alkanesulfonyl,2-C12haloalkylthio,2-C12haloalkaliphilic,2-C12haloalkaliphilic,2-C12alinytjara,2-C12alkylsulfonyl,2-C12alkylsulfonyl,1-C4alkyl-S(O)2O, phenyl-S(O)2O, (C1-C4alkoxy)2P(O)O1-C4alkyl(C1-C4alkoxy)P(O)O, N(C1-C4alkoxy)P(O)O1-C12alkyl-S(CO)O, benzyloxy, fenoxaprop, phenylthiourea, phenylsulfinyl or phenylsulfonyl, with the phenyl group can be in turn substituted With1-C4the alkyl, C1-C4haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,1-C4alkylcarboxylic,1-C4alkoxycarbonyl,1-C4alkylaminocarbonyl, di(C1-C4alkyl)amino group, a C1-C4alkylthiol,1-C4alkylsulfonyl,1-C4alkylsulfonyl, group C1-C4alkyl-S(O)2O1-C4haloalkylthio,1-C4haloalkylthio,1-C4haloalkylthio, group C1-C4haloalkyl-S(O)2O, g is uppoi 1-C4alkyl-S(O)2NH1-C4alkyl-S(O)2N(C1-C4by alkyl), halogen, the nitro-group or a cyano,

R31and R32each independently of one another denotes hydrogen or C1-C4alkyl,

R33and R34each independently from each other mean a hydrogen, a hydroxy-group, With1-C4alkyl, C2-C6alkenyl,2-C6quinil,1-C4alkoxycarbonyl, C1-C6allylthiourea, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, C1-C4alkyl-NHS(O)2With1-C4haloalkyl, -NH-C1-C4alkyl, -N(C1-C4alkyl)2C1-C6alkoxygroup, a cyano, a nitro-group, halogen or phenyl, which may be in turn substituted With1-C4the alkyl, C1-C4haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,1-C4alkylcarboxylic,1-C4alkoxycarbonyl, amino group, With1-C4alkylaminocarbonyl, di(C1-C4alkyl)amino group, With1-C6alkylthiol, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, group C1-C4alkyl-S(O)2O1-C4haloalkylthio,1-C4haloalkyl what heniam, With1-C4haloalkylthio, group C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH1-C4alkyl-S(O)2N(C1-C4by alkyl), halogen, a nitro-group, a group COOH or by cyano, or R33and R34together form a2-C6Allenby bridge, and

R35means hydrogen, C1-C4alkyl, C1-C4alkoxycarbonyl or phenyl, which may be in turn substituted With1-C4the alkyl, C1-C4haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,1-C4alkylcarboxylic,1-C4alkoxycarbonyl, amino group, With1-C4alkylaminocarbonyl, di(C1-C4alkyl)amino group, With1-C4alkylthiol,1-C4alkylsulfonyl,1-C4alkylsulfonyl, group C1-C4alkyl-S(O)2O1-C4haloalkylthio,1-C4haloalkylthio,1-C4haloalkylthio, group C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH1-C4alkyl-S(O)2N(C1-C4by alkyl), halogen, a nitro-group, a COOH group or a cyano, or a group Q5

in which

Z denotes sulfur, SO or SO2,

R01means hydrogen, C1-C8alkyl or C1-C8alkyl substituted by halogen, C1-C4alkoxygroup,1-C4alkylthiol,1-C4alkylsulfonyl,1-C4alkylsulfonyl, hydroxy-group, a cyano, a nitro-group, group-SNO group,- CO2R02group-COR03group-COSR04group-NR05R06a group CONR036R037or phenyl, which may be in turn substituted With1-C4the alkyl, C1-C6haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy, C2-C6alkenyl,3-C6the quinil,3-C6alkenylacyl,3-C6alkyloxy, a halogen, a nitro-group, a cyano group,- COOH, SOOS1-C4the alkyl, Sofinim,1-C4alkoxygroup, fenoxaprop, (C1-C4alkoxy)-C1-C4the alkyl, (C1-C4alkylthio)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, NHSO2-C1-C4the alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2-C1-C4the alkyl, N(C1-the 6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2-C1-C4the alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6quinil)SO2-C1-C4the alkyl, N(C3-C6quinil)SO2-phenyl, N(C3-C7cycloalkyl)SO2-C1-C4the alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2-C1-C4the alkyl, N(phenyl)SO2-phenyl, OSO2-C1-C4the alkyl group CONR025R026, OSO2-C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthiol,1-C4haloalkylthio, phenylthiourea,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfonyl,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfinyl,1-C4alkylammonium or the group-NR015CO2R027or

R01means2-C8alkenyl or2-C8alkenyl, substituted with halogen, C1-C4alkoxygroup,1-C4alkylthiol,1-C4alkylsulfonyl,1-C4alkylsulfonyl, group-CONR032R033, a cyano, a nitro-group, group-SNO group,- CO2R038group-COR039, -COS-C1-C4Alki the Ohm, the group-NR034R035or phenyl, which may be in turn substituted With1-C4the alkyl, C1-C6haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,2-C6alkenyl,3-C6the quinil,3-C6alkenylacyl,3-C6alkyloxy, a halogen, a nitro-group, a cyano group,- COOH, SOOS1-C4the alkyl, Sofinim,1-C4alkoxygroup, fenoxaprop, (C1-C4alkoxy)-C1-C4the alkyl, (C1-C4alkylthio)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, NHSO2-C1-C4the alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2-C1-C4the alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2-C1-C4the alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6quinil)SO2-C1-C4the alkyl, N(C3-C6quinil)SO2-phenyl, N(C3-C7cycloalkyl)SO2-C1-C4the alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2-C1-C4the alkyl, N(phenyl)SO2-phenyl, OSO2-C1-C the alkyl group CONR040R041, OSO2-C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthiol,1-C4haloalkylthio, phenylthiourea, C1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfonyl,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfinyl,1-C4alkylammonium or the group-NR043CO2R042or

R01means3-C6quinil or3-C6quinil, substituted with halogen, C1-C4haloalkyl, cyano, -CO2R044or phenyl, which may be in turn substituted With1-C4the alkyl, C1-C6haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,1-C6alkenyl,3-C6the quinil,3-C6alkenylacyl,3-C6alkyloxy, a halogen, a nitro-group, a cyano group,- COOH, SOOS1-C4the alkyl, Sofinim,1-C4alkoxygroup, fenoxaprop, (C1-C4alkoxy)-C1-C4the alkyl, (C1-C4alkylthio)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1 4the alkyl, NHSO2-C1-C4the alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2-C1-C4the alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2-C1-C4the alkyl, N(C2-C6alkenyl)SO2-phenyl, R(C3-C6quinil)SO2-C1-C4the alkyl, N(C3-C6quinil)SO2-phenyl, N(C3-C7cycloalkyl)SO2-C1-C4the alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2-C1-C4the alkyl, N(phenyl)SO2-phenyl, OSO2-C1-C4the alkyl group CONR028R029, OSO2-C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthiol,1-C4haloalkylthio, phenylthiourea,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfonyl,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfinyl,1-C4alkylammonium or the group-NR031CO2R030or

R01means3-C7cycloalkyl or3-C7cycloalkyl, substituted C1-C4the alkyl, C1-C4alkoxygroup,1-C4alkylthiol,1-C4alkylsulfonyl,1-C4 alkylsulfonyl or phenyl, which may be in turn substituted with halogen, a nitro-group, cyano, C1-C4alkoxygroup,1-C4haloalkoxy,1-C4alkylthiol,1-C4haloalkylthio,1-C4the alkyl or C1-C4haloalkyl, or

R01means1-C4alkylen-C3-C7cycloalkyl, phenyl or phenyl substituted With1-C4the alkyl, C1-C6haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,2-C6alkenyl,3-C6the quinil,3-C6alkenylacyl,3-C6alkyloxy, a halogen, a nitro-group, a cyano group,- COOH, SOOS1-C4the alkyl, Sofinim,1-C4alkoxygroup, fenoxaprop, (C1-C4alkoxy)-C1-C4the alkyl, (C1-C4alkylthio)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, NHSO2-C1-C4the alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2-C1-C4the alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2-C1-C4the alkyl, N(C2-C 6alkenyl)SO2-phenyl, N(C3-C6quinil)SO2-C1-C4the alkyl, N(C3-C6quinil)SO2-phenyl, N(C3-C7cycloalkyl)SO2-C1-C4the alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2-C1-C4the alkyl, N(phenyl)SO2-phenyl, OSO2-C1-C4the alkyl group CONR045R046, OSO2-C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthiol,1-C4haloalkylthio, phenylthiourea,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfonyl,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfinyl or the group-NR048CO2R047or

R01means1-C4alkylether, COR07or a 4-6-membered heterocyclyl,

R02, R038, R044and R066each independently of one another denotes hydrogen, C1-C4alkyl, phenyl or phenyl substituted With1-C4the alkyl, C1-C6haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,2-C6alkenyl,3-C6the quinil,3-C6alkenylacyl,3-C6alkyloxy, halogen, nitro group is th, a cyano group,- COOH, SOOS1-C4the alkyl, Sofinim,1-C4alkoxygroup, fenoxaprop, (C1-C4alkoxy)-C1-C4the alkyl, (C1-C4alkylthio)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, NHSO2-C1-C4the alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2-C1-C4the alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2-C1-C4the alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6quinil)SO2-C1-C4the alkyl, N(C3-C6quinil)SO2-phenyl, N(C3-C7cycloalkyl)SO2-C1-C4the alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2-C1-C4the alkyl, N(phenyl)SO2-phenyl, OSO2-C1-C4the alkyl group CONR049R050, OSO2-C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthiol,1-C4haloalkylthio, phenylthiourea,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfonyl,1-C4alkylsulfonyl,1-C4haloalkylthio, Hairdryer what sulfinyl, -C1-C4alkylphenyl or the group-NR052CO2R053,

R03, R039and R067each independently from each other mean With1-C4alkyl, phenyl or phenyl substituted With1-C4the alkyl, C1-C6haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,2-C6alkenyl,3-C6the quinil,3-C6alkenylacyl,3-C6alkyloxy, a halogen, a nitro-group, a cyano group,- COOH, SOOS1-C4the alkyl, Sofinim,1-C4alkoxygroup, fenoxaprop, (C1-C4alkoxy)-C1-C4the alkyl, (C1-C4alkylthio)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, NHSO2-C1-C4the alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2-C1-C4the alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2-C1-C4the alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6quinil)SO2-C1-C4the alkyl, N(C3-C6quinil)SO2-phenyl, N(C3-C7cycloalkyl)SO2-C1-C4the alkyl, N(C3-C7 cycloalkyl)SO2-phenyl, N(phenyl)SO2-C1-C4the alkyl, N(phenyl)SO2-phenyl, OSO2-C1-C4the alkyl group CONR068R054, OSO2-C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthiol,1-C4haloalkylthio, phenylthiourea,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfonyl,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfinyl, -(CH2)tthe phenyl or the group-NR056CO2R055,

R04means1-C4alkyl,

R05means hydrogen, C1-C4alkyl, C2-C6alkenyl,3-C6quinil,3-C7cycloalkyl, phenyl or phenyl substituted With1-C4the alkyl, C1-C6haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,2-C6alkenyl,3-C6the quinil,3-C6alkenylacyl,3-C6alkyloxy, a halogen, a nitro-group, a cyano group,- COOH, SOOS1-C4the alkyl, Sofinim,1-C4alkoxygroup, fenoxaprop, (C1-C4alkoxy)-C1-C4the alkyl, (C1-C4alkylthio)-C1-C4Ala is scrap, (C1-C4alkylsulfonyl)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, NHSO2-C1-C4the alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2-C1-C4the alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2-C1-C4the alkyl, N(C2-C6alkenyl)SO2-phenyl, a group N(C3-C6quinil)SO2N, N(C3-C6quinil)SO2-C1-C4the alkyl, N(C3-C6quinil)SO2-phenyl, a group N(C3-C7cycloalkyl)SO2H, N(C3-C7cycloalkyl)-SO2-C1-C4the alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2-C1-C4the alkyl, N(phenyl)SO2-phenyl, OSO2-C1-C4the alkyl group CONR057R058, OSO2-C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthiol,1-C4haloalkylthio, phenylthiourea,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfonyl,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfinyl,1-C4alkylammonium or the group-NR060CO2R059,

R06means hydrogen, C1-C42-C6alkenyl,3-C6quinil,3-C7cycloalkyl, phenyl or phenyl substituted With1-C4the alkyl, C1-C6haloalkyl,1-C4alkoxygroup,1-C4haloalkoxy,2-C6alkenyl,3-C6the quinil,3-C6alkenylacyl,3-C6alkyloxy, a halogen, a nitro-group, a cyano group,- COOH, SOOS1-C4the alkyl, Sofinim,1-C4alkoxygroup, fenoxaprop, (C1-C4alkoxy)-C1-C4the alkyl, (C1-C4alkylthio)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, (C1-C4alkylsulfonyl)-C1-C4the alkyl, NHSO2-C1-C4the alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2-C1-C4the alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2-C1-C4the alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6quinil)SO2-C1-C4the alkyl, N(C3-C6quinil)SO2-phenyl, N(C3-C7cycloalkyl)SO2-C1-C4the alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2-C1-C4the alkyl, N(phenyl)SO2-penelo is, OSO2-C1-C4the alkyl group CONR061R062, OSO2-C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthiol,1-C4haloalkylthio, phenylthiourea,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfonyl,1-C4alkylsulfonyl,1-C4haloalkylthio, phenylsulfinyl,1-C4alkylammonium or the group-NR064CO2R063,

R07means phenyl,1-C4alkyl, C1-C4alkoxygroup or-NR08R09, R08and R09each independently from each other mean With1-C4alkyl, phenyl or phenyl substituted by halogen, a nitro-group, cyano, C1-C4the alkyl, C1-C4alkoxygroup,1-C4thioalkyl, group-CO2R066group-COR067With1-C4alkylsulfonyl,1-C4alkylsulfonyl or1-C4haloalkyl, or R08and R09together form a 5 - or 6-membered ring which may be interrupted by oxygen, a group NR065or S atom,

R015, R031, R043, R048, R052, R056, R060and R064each independently of one another denotes hydrogen, C1-C4alkyl, C2-C 6alkenyl,3-C6quinil or3-C7cycloalkyl,

R025, R026, R027, R028, R029, R030, R032, R033, R034, R035, R036, R037, R040, R041, R042, R045, R046, R047, R049, R050, R053, R054, R055, R057, R058, R059, R061, R062, R063, R065and R068each independently of one another denotes hydrogen, C1-C4alkyl, C2-C6alkenyl,3-C6quinil,3-C7cycloalkyl, phenyl or phenyl substituted by halogen, a nitro-group, cyano, C1-C4alkoxygroup,1-C4haloalkoxy,1-C4alkylthiol,1-C4haloalkylthio,1-C4the alkyl or C1-C4haloalkyl, and

R36means1-C4alkyl, C1-C4haloalkyl,3-C6alkenyl,3-C6haloalkyl,3-C6quinil,3-C6haloalkyl,3-C6cycloalkyl or3-C6cycloalkyl, substituted with halogen, C1-C4the alkyl, C1-C4haloalkyl,3-C6alkenyl,3-C6haloalkyl,3-C6the quinil,3-C6haloalkyl,1-C 4alkoxycarbonyl,1-C4alkylthiol,1-C4alkylsulfonyl,1-C4alkylsulfonyl,1-C4haloalkylthio,1-C4haloalkylthio,1-C4haloalkylthio,1-C4alkylcarboxylic, di(C1-C4alkyl)amino group, With1-C4alkoxygroup,1-C4haloalkoxy, group C1-C4alkyl-S(O)2O group C1-C4haloalkyl-S(O)2O or phenyl, which may be in turn substituted with halogen, C1-C4the alkyl, C1-C4haloalkyl,3-C6alkenyl,3-C6the quinil, a cyano, a nitro-group or COOH group,

or agronomically acceptable salts of such compounds and

b) a synergistically effective amount of one or more compounds selected from the group including

the compound of formula 2.1

in which R51means of CH2-OMe, ethyl or hydrogen, a R52means hydrogen, or R51and R52together represent a group-CH=CH-CH=CH-,

the compound of formula 2.2

in which R53means ethyl, R54means methyl or ethyl, a R55means-CH(Me)-CH2OMe, <S>-CH(Me)-CH2OMe, sub> 2OMe or CH2O-CH2CH3,

the compound of formula 2.3

in which R56means CH(Me)-CH2OMe or <S>CH(Me)-CH2OMe,

the compound of formula 2.4

in which R57means chlorine, methoxy group or metalcorp, R58means ethyl, a R59means ethyl, isopropyl, -C(CN)(CH3)-CH3or tert-butyl,

the compound of formula 2.5

in which R60means ethyl or n-propyl, R61means soo-1/s++, -CH2-CH(Me)S-CH2CH3or groupand X is oxygen, N-O-CH2CH3or N-O-CH2CH=CH-Cl,

the compound of formula 2.6

in which R62means hydrogen, a methoxy group or ethoxypropan, R63means hydrogen, methyl, methoxy group or a fluorine, R64means the Sooma, fluorine or chlorine, R65means hydrogen or methyl, Y represents Metin, C-F or nitrogen, Z means Metin or nitrogen, a R66means fluorine or chlorine,

the compound of formula 2.7

in which R67means hydrogen or-C(O)-S-n-octyl,

the compound of formula 2.8

in which R68means bromine or iodine,

the is a group of formula 2.9

in which R69means chlorine or nitro-group,

the compound of formula 2.10

in which R70means fluorine or chlorine, a R71means-CH2-CH(Cl)-SOON2CH3or-NH-SO2Me,

the compound of formula 2.11

in which R72means trifluoromethyl or chlorine,

the compound of formula 2.12

in which R73mean NH2or <S>NH2,

the compound of formula 2.13

in which Y1means nitrogen, Metin, NH-CHO, or N-Me, Y2means nitrogen, Metin or C-I, Y3means Metin, Y4means Metin or Y3and Y4together mean sulfur or-Cl, Y5mean nitrogen or Metin, Y6means methyl, dipterocarp, trifluoromethyl or methoxy group, Y7means a methoxy group or dipterocarp, a R74means CONMe2, COOMe, SOOS2H5, trifluoromethyl, CH2-CH2CF3or SO2CH2CH3or its sodium salt ("Me" in each case means a methyl group),

the compound of formula 2.13.c

the compound of formula 2.14

the compound of formula 2.15

the compound of formula 2.16

the compound of formula 2.17

the compound of formula 2.18

the compound of formula 2.19

the compound of formula 2.20

the compound of formula 2.21

the compound of formula 2.22

the compound of formula 2.23

the compound of formula 2.24

the compound of formula 2.25

the compound of formula 2.26

the compound of formula 2.27

the compound of formula 2.28

the compound of formula 2.29

the compound of formula 2.30

the compound of formula 2.31

the compound of formula 2.32

the compound of formula 2.33

the compound of formula 2.34

the compound of formula 2.35

the compound of formula 2.36

the compound of formula 2.37

the compound of formula 2.38

the compound of formula 2.39

the compound of formula 2.40

the compound of formula 2.41

the compound of formula 2.42

the compound of formula 2.43

the compound of formula 2.44

the compound of formula 2.45

the compound of formula 2.46

the compound of formula 2.47

the compound of formula 2.48

the compound of formula 2.49

the compound of formula 2.50

and the compound of formula 2.51

In the above formulas, "Me" means methyl group. Alkyl groups, the above values of the substituents may be branched or straight chain and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl, and their branched isomers. Alcox the-, alkeneamine and alkyline radicals are derived from the above alkyl radicals. Alkeneamine and alkyline groups can be single or multiply unsaturated.

Allenova group may be substituted by one or more methyl groups, such alkylene groups are preferably in each case unsaturated. The same applies to all3-C5cycloalkyl-From3-C5oxocyclohexyl-From3-C5talklounge-From3-C4dioxocyclohexa-From3-C4directlly-From3-C4oxadiazolyl and N(CH2)-containing groups.

Under the halogen usually refers to fluorine, chlorine, bromine or iodine. The same correspondingly applies to the halogen included in the various groups, such as haloalkyl or halophenol.

Haloalkyl groups having a chain length of from 1 to 6 carbon atoms are, for example, vermeil, deformity, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-triptorelin, 2-foretel, 2-chloroethyl, pentafluoroethyl, 1,1-debtor-2,2,2-trichloroethyl, 2,2,3,3-tetraborate and 2,2,2-trichlorethyl, pentafluoroethyl, getattr-n-propyl, PERFLUORO-n-hexyl, while the preferred haloalkyl groups specified in the values of the substituents R2, R3and above all, R5are trichlo is methyl, dichloromethyl, diperchlorate, deformity, trifluoromethyl, pentafluoroethyl or heptamer-n-propyl.

Appropriate haloalkyl radicals are alkeneamine group, one - or multi-substituted with halogen, fluorine, chlorine, bromine or iodine and especially fluorine or chlorine, for example 2,2-debtor-1-methylvinyl, 3-forproper, 3-chloropropionyl, 3-bromopropionyl, 2,3,3-triptocaine, 2,3,3-trichlorpropane and 4,4,4-triflorum-2-EN-1-yl. Preferred C2-C12alkeneamine radicals, one-, two -, or three times substituted by halogen, have a chain length of from 2 to 5 carbon atoms. Appropriate haloalkyl radicals are alkyline group, one - or multi-substituted with halogen, bromine or iodine and especially fluorine or chlorine, for example 3-forproposal, 3-chloropropionyl, 3-bromopropyl, 3,3,3-triptocaine and 4,4,4-triflorum-2-in-1-yl. Preferred alkyline group, one - or multi-substituted with halogen, have a chain length of from 2 to 5 carbon atoms.

Alkoxygroup preferably have a chain length of 1 to 6 carbon atoms. As an example of alkoxygroup can be called methoxy-, ethoxy-, propoxy-, isopropoxy, h-butoxy, isobutoxy-, second -, butoxy - or tert-butoxypropan or pentyloxy or hexyloxyphenol, while the preferred methoxy - and etok the group. Alkylsulphonyl preferably represents acetyl or propionyl. Examples of alkoxycarbonyl are methoxycarbonyl, etoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxide, second-butoxycarbonyl or tert-butoxycarbonyl, while the preferred methoxycarbonyl, etoxycarbonyl or tert-butoxycarbonyl.

Haloalkoxy preferably have a chain length of from 1 to 8 carbon atoms. As examples of haloalkoxy can be called formatexpr, dipterocarp, cryptometer, 2,2,2-triptracker, 1,1,2,2-tetrafluoroethoxy, 2-floridacheap, 2-chlorethoxyfos, 2,2-dipterocarp or 2,2,2-trichlorethene, while the preferred dipterocarp, 2-chlorethoxyfos or tripterocarpa.

Ancilliary preferably have a chain length of from 1 to 8 carbon atoms. Examples of ancilliary are methylthiourea, ethylthiourea, PropertyGroup, isopropylthio, n-butylthiourea, isobutylthiazole, second-butylthiourea or tert-butylthiourea, while the preferred methylthio - or ethylthiourea.

Alkylsulfonyl represents, for example, methylsulfinyl, ethylsulfinyl, propylsulfonyl, isopropylphenyl, n-butylsulfonyl, isobutylphenyl, second-butylsulfonyl or tert-butyls lynel, preferably methylsulfinyl or ethylsulfinyl.

Alkylsulfonyl is, for example, methylsulphonyl, ethylsulfonyl, propylsulfonyl, isopropylphenyl, n-butylsulfonyl, isobutylphenyl, second-butylsulfonyl or tert-butylsulfonyl, preferably methylsulphonyl or ethylsulfonyl.

Alkylamino represents, for example, methylaminopropyl, ethylamino, n-propylamino, isopropylamino or isomer of butylamine. Dialkylamino represents, for example, dimethylaminopropyl, methylaminopropyl, diethylaminopropyl, n-propylethylene, dibutylamino or diisopropylamino. Preferred alkylamino with chain length from 1 to 4 carbon atoms.

Alkoxyalkyl groups preferably have from 1 to 6 carbon atoms. As examples of alkoxyalkyl can be called methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxyphenyl or isopropoxide.

Alkylthiomethyl groups preferably have from 1 to 6 carbon atoms. As examples of alkylthiomethyl can be called methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiouracil, n-propylthiouracil, isopropylaminomethyl, isopropylaminoethyl, butylthioethyl, butylthioethyl or butylthioethyl.

Cycloalkyl group p is edocfile have from 3 to 6 ring carbon atoms and may be substituted by one or more methyl groups, however, the preferred unsubstituted cycloalkyl groups, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Phenyl, including as a structural fragment of one or another substituent, such as fenoxaprop, benzyl, benzyloxy, benzoyl, phenylthiourea, phenylalkyl, phenoxyethyl or tosyl, may be present in mono - or polishmaster, while the substituents depending on the specific requirements can be ortho-, meta - and/or para-position(s).

In the scope of the present invention also includes salts of the compounds of formula I, these compounds are able to form with amines, bases of alkaline and alkaline-earth metal or Quaternary ammonium bases. Among used as salt-forming agents are hydroxides of alkali and alkaline-earth metals, one should highlight the hydroxides of lithium, sodium, potassium, magnesium and calcium, especially the hydroxides of sodium and potassium.

As examples of amines suitable for the formation of ammonium salts include ammonia and primary, secondary, and tertiary1-C18the bonds alkylamines,1-C4hydroxyethylamine and C2-C4alkoxyalkyl, such as methylamine, ethylamine, n-Propylamine, Isopropylamine, the four isomeric state of butylamine, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylic, hexadecylamine, heptadecyl, octadecylamine, methylethylamine, metrizability, methylhexanamine, methylenediamine, methylpentadiene, methyloctadecane, ethylbutylamine, ethylheptylamino, atractylis, vexillationes, getselection, dimethylamine, diethylamine, di-n-Propylamine, Diisopropylamine, di-n-butylamine, di-n-amylamine, vitaminen, digoxigenin, gigatronik, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, N,N-diethanolamine, N-ethylpropylamine, N-butylethylamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutene-2-amine, dibutyl-2-amine, n-hexenyl-2-amine, Propylenediamine, trimethylamine, triethylamine, tri-n-Propylamine, triisopropanolamine, tri-n-butylamine, triisobutylene, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and amoxicillin, heterocyclic amines such as pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, Hinkley and asain, primary arylamine, such as anilines, methoxyaniline, ethoxyaniline, o-, m - and n-toluidine, phenylenediamine, benzidine, naphthylamines and o-, m - and n-chloraniline, but primarily triethylamine, Isopropylamine and Diisopropylamine.

With the invention it has been unexpectedly found that the effect of the application of the combination of the active ingredient of formula I with one or bore alkemi active ingredients from among the compounds of formulae 2.1 to 2.51 exceeds in weed control total effect which in principle would be expected from the use of such active ingredients separately, due to the spectrum of each of these individual active ingredients extends primarily from the following two aspects. The first one is to reduce the consumption rates of the individual compounds of formulas I and 2.1-2.51, while maintaining their actions at a sufficiently high level, and the second is that proposed in the invention composition makes it possible to combat weeds, even in cases where the application of the individual compounds in small doses is impractical and inefficient from agronomic point of view. In the result it is possible to considerably broaden the spectrum of weeds that need to fight, and further improve the selectivity in crops of useful plants, which is a necessary condition for unintentional overdose of the active ingredient. Proposed in the invention composition not only provides a highly efficient destruction of weeds in crops of useful plants, but also provides more freedom of choice of crops to be grown later in the same areas.

Proposed in the invention composition can be used to combat the wide range of agronomically important weeds, such as Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica. The composition according to the invention permits its use in all methods commonly used in agriculture, and, in particular, suitable for predsjedava processing, post-harvest processing and handling of seeds. Proposed in the invention is a composition suitable for control of weeds, especially in crops such useful plants as cereals, rape, sugar beet, sugar cane, plantation crops, rice, maize and soybean, as well as for selective weed control.

Under the "cultures" in the context of the present invention are also culture, which as a result of conventional methods of breeding or genetic engineering was developed tolerance to herbicides or whole classes.

Preferred compositions according to the invention contain compounds of the formula I, in which

R in each case independently denotes hydrogen, C1-C6alkyl, C2-C6alkenyl,2-C6haloalkyl,2-C6quinil,2-C6haloalkyl,3-C6cycloalkyl, C1-C6alkoxygroup, C1-C6haloalkoxy, C1-C 6allylthiourea, C1-C6alkylsulfonyl, C1-C6alkylsulfonyl, C1-C6haloalkyl, C1-C6haloalkylthio, C1-C6haloalkaliphilic,C1-C6haloalkaliphilic, C1-C6alkoxycarbonyl, C1-C6alkylsulphonyl,1-C6alkylamino, di(C1-C6alkyl)amino group, a C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminosulfonyl, -N(R1)-S-R2, -N(R3)SO-R4, -N(R5)-SO2-R6the nitrogroup, cyano, halogen, a hydroxy-group, amino group, menzilcioglu, benzylmorphine, bansilalpet, phenyl, fenoxaprop, phenylthiourea, phenylsulfinyl or phenylsulfonyl, with the phenyl group can be, in turn, mono-, di - or tizamidine C1-C6the alkyl, C1-C6haloalkyl,3-C6alkenyl,3-C6haloalkyl,3-C6the quinil,3-C6haloalkyl, C1-C6alkoxygroup, C1-C6haloalkoxy,3-C6alkenylacyl,3-C6alkynylamino, mercaptopropyl,1-C6alkylthiol,1-C6haloalkylthio,3-C6alkenylsilanes,3-C6haloalkylthio,3 -C6alkylalcohol,2-C5alkoxyalkanols,3-C5acetylacetonato,3-C6alkoxycarbonylmethyl,2-C4cyanoacetylurea,1-C6alkylsulfonyl,1-C6haloalkylthio,1-C6alkylsulfonyl,1-C6haloalkylthio, aminosulfonyl,1-C2alkylaminocarbonyl,2-C4dialkylaminoalkyl, group C1-C3alkylen-R45group NR46R47, a halogen, a cyano, a nitro-group, a phenyl or menzilcioglu, with the latter two groups that are phenyl and menzilcioglu, in turn, can be substituted in the phenyl ring C1-C3the alkyl, C1-C3haloalkyl, C1-C3alkoxygroup, C1-C3haloalkoxy, halogen, cyano or nitro-group, or

R in each case independently denotes monocyclic or condensed bicyclic ring system with 5 to 10 members, which may be aromatic or partially saturated and can contain 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, this ring system either directly attached to the pyridine ring, or attached to the pyridine ring is through With 1-C4alkylenes group, and each ring system may not contain more than two oxygen atoms and cannot contain more than two sulfur atoms, and the said ring system may be, in turn, mono-, di - or tizamidine C1-C6the alkyl, C1-C6haloalkyl,3-C6alkenyl,3-C6haloalkyl,3-C6the quinil,3-C6haloalkyl,1-C6alkoxygroup,1-C6haloalkoxy,3-C6alkenylacyl,3-C6alkynylamino, mercaptopropyl, C1-C6alkylthiol, C1-C6haloalkylthio,3-C6alkenylsilanes,3-C6haloalkylthio,3-C6alkylalcohol,2-C5alkoxyalkanols,3-C5acetylacetonato,3-C6alkoxycarbonylmethyl,2-C4cyanoacetylurea, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6alkylsulfonyl,1-C6haloalkylthio, aminosulfonyl,1-C2alkylaminocarbonyl,2-C4dialkylaminoalkyl, group C1-C3alkylen-R7group NR8R9, halogen, cyano, neath what agropol, the phenyl or menzilcioglu, and phenyl and menzilcioglu, in turn, can be substituted in the phenyl ring C1-C3the alkyl, C1-C3haloalkyl, C1-C3alkoxygroup, C1-C3haloalkoxy, halogen, cyano or nitro-group, with R1, R2, R3, R4, R5, R6, R7, R8, R9, R45, R46and R47have the above values, and the substituents at the nitrogen atom in the heterocyclic ring are different from halogen.

Another group of preferred compositions according to the invention include compositions that as the compounds of formula I contain a compound of the formula Ia

in which

R48means C1-C6alkyl, C2-C6alkenyl,2-C6haloalkyl,2-C6quinil,2-C6haloalkyl,3-C6cycloalkyl, C1-C6haloalkyl or monocyclic or condensed bicyclic ring system with 5 to 10 members, which may be aromatic or partially saturated and can contain 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, and such ring system either directly attached to the pyridine ring, or attached to the pyridine ring via the 1-C4alkylenes group, and each ring system may not contain more than two oxygen atoms and cannot contain more than two sulfur atoms, and the said ring system may be, in turn, mono-, di - or tizamidine C1-C6the alkyl, C1-C6haloalkyl,3-C6alkenyl,3-C6haloalkyl,3-C6the quinil,3-C6haloalkyl, C1-C6alkoxygroup, C1-C6haloalkoxy,3-C6alkenylacyl,3-C6alkynylamino, mercaptopropyl,1-C6alkylthiol,1-C6haloalkylthio,3-C6alkenylsilanes,3-C6haloalkylthio,3-C6alkylalcohol,2-C5alkoxyalkanols,3-C5acetylacetonato,3-C6alkoxycarbonylmethyl,2-C4cyanoacetylurea, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6alkylsulfonyl, C1-C6haloalkylthio, aminosulfonyl,1-C2alkylaminocarbonyl,2-C4dialkylaminoalkyl, group C1-C3alkylen-R7group NR8R9, halogen, cyano, NITR the group, the phenyl or menzilcioglu, with phenyl and menzilcioglu, in turn, can be substituted in the phenyl ring C1-C3the alkyl, C1-C3haloalkyl, C1-C3alkoxygroup, C1-C3haloalkoxy, halogen, cyano or nitro-group, and the substituents at the nitrogen atom in the heterocyclic ring are different from halogen,

R49means hydrogen, C1-C6alkyl, C1-C6haloalkyl, halogen or phenyl which may be substituted C1-C3the alkyl, C1-C3haloalkyl, C1-C3alkoxygroup, C1-C3haloalkoxy, halogen, cyano or nitro-group,

R50means C1-C6haloalkyl and

R7, R8, R9and Q have the above values.

Among this group of compounds, preferred compounds in which R48means C1-C6alkyl, C2-C6alkenyl,2-C6haloalkyl,2-C6quinil,2-C6haloalkyl,3-C6cycloalkyl or C1-C6haloalkyl.

Preferred compositions in which in formula I, Q means a group of Q2or3where first of all in the group Q2R23means a hydroxy-group, and the group Q3R40also means a hydroxy-group. Cf is di this group it is necessary to emphasize the connection in which m is 2 and one substituent R represents a C1-C4alkoxy-C1-C4alkyl or C1-C4alkoxy-C1-C4alkoxy-C1-C4alkyl.

Other preferred synergistic effect of the mixture according to the invention contain as active ingredient a compound of the formula I and either a compound of formula I

or a compound of the formula 2.2.b

or a compound of formula 2.2, in which R3means ethyl, R4means methyl, and R5means ethoxymethyl, or a compound of formula 2.2, in which R3means ethyl, R4means ethyl, a R5means methoxymethyl, or a compound of formula 2.3, or a compound of the formula 2.30, or the compound of formula 2.4, or a compound of formula 2.13, or a compound of the formula 2.14, or the compound of formula 2.6, in which R12means hydrogen, Z means Metin, R13means methyl, Y represents nitrogen, R14means fluorine, R15means hydrogen, a R16means fluorine, or R12means a methoxy group, Z means Metin, R13means a methoxy group, Y means Metin, R14means chlorine, R15means methyl, and R16means chlorine or a compound of formula 2.7, in which R17means-C(O)-S-n-octyl, or connect the exclusion of the General formula 2.12, or a compound of the formula 2.18, or a compound of the formula 2.19, or a compound of the formula 2.21, or a compound of the formula 2.25, or a compound of the formula 2.33, or a compound of the formula 2.45, or a compound of formula 2.1.

Particularly preferred synergistic effect of the mixture according to the invention contain as active ingredient a compound of the formula I and either a compound of formula I

or a compound of the formula 2.2.b

or a compound of formula 2.2, in which R3means ethyl, R4means methyl, and R5means ethoxymethyl, or a compound of formula 2.2, in which R3means ethyl, R4means ethyl, a R5means methoxymethyl, or a compound of formula 2.3, or a compound of the formula 2.30.

The most effective are, it has been found that combinations of compounds of the formula I with the compound of the formula I

at the same time as the compounds of formula I is most preferable to use the compound 1.001 specified below in table 1.

The compounds of formula I can be obtained similarly to the method described in WO 97/46530,

(a) the interaction of the compounds of formula II

in which R and m have the above for formula I value, and X denotes a leaving group, e.g. the measures halogen, in an inert organic solvent in the presence of a base with the compound of the formula III, IV, V or VI

where R20, R23, R30and R40means a hydroxy-group, and the remaining substituents have the above for formula I, with the receipt of the compounds of formula VII, VIII, IX or X

and subsequent isomerization of this connection, for example, in the presence of a base and catalytic amounts of dimethylaminopyridine (DMAP) or in the presence of a source of cyanide, or

b) the interaction of the compounds of formula XI

in which R and m have the above for formula I, with a compound of formula III, IV, V or VI in an inert organic solvent in the presence of a base agent and the combination with obtaining the compounds of formula VII, VIII, IX or X and subsequent isomerization of this connection, for example, by the method described above for option a).

The compounds of formula I in which Q represents a group of Q5

where Z denotes sulfur, and R36and R01have the above for formula I values can be obtained analogously to known methods described, for example, in WO 97/43270), or

a) converting the compounds of formula XII

in which R36, R and m have the above meanings, in the presence of a base, carbon disulfide and alkilirutego agent of the formula XIII

R01-X1(XIII)

in which R01is the above for formula I value a X1means a leaving group such as halogen or sulfonate, in the compound of formula XIV

in which Z denotes sulfur, a R, R01, R36and m have the above values, and then the cyclization of this compound with hydroxylamine hydrochloride, optionally in a solvent, in the presence of a base to obtain the compounds of formula Ie

in which Z denotes sulfur, a R, R36, R01and m have the above values, with subsequent oxidation of this compound by the appropriate oxidant such as meta-chloroperbenzoic acid (m-HPBC).

The method of obtaining compounds of formula I in more detail is shown in the following reaction schemes 1 and 2.

In accordance with the above reaction scheme can be obtained primarily compounds of the formula I containing groups of Q1, Q2, Q3and Q4in which R20, R23,R 30and R40means a hydroxy-group.

To obtain compounds of the formula I in which Q represents one of the groups Q1-Q4,a R20, R23, R30and R40means a hydroxy-group in the starting materials used according to reaction scheme 1, a), derivatives of carboxylic acids of the formula II in which X signifies a leaving group, for example halogen, such as iodine, bromine or primarily chlorine, N-oxyproline or N,O-dimethylhydroxylamine, or a residue in the form of activated complex ester, for example(obtained from dicyclohexylcarbodiimide (DCC) and acceptable carboxylic acid) or(obtained from N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide (EDC) and acceptable carboxylic acid). These compounds in an inert organic solvent, for example in a halogenated hydrocarbon, such as dichloromethane, a nitrile, such as acetonitrile, or an aromatic hydrocarbon, such as toluene, in the presence of a base, such as alkylamine, such as triethylamine, an aromatic amine such as pyridine or 4-dimethylaminopyridine (DMAP), is subjected to the interaction with donovani derivatives of the formula III, IV, V or VI with getting isomeric enol ethers of formula VII, VIII, IX and X according to the government. Etherification occurs at a temperature of from 0 to 110°C.

Isomerization ester derivatives of formulas VII, VIII, IX and X with getting deanovich derivatives of the formula I (in which R20, R23, R30and R40means a hydroxy-group) can be performed, for example, as described in EP 0369803 method in the presence of a base, such as alkylamine, such as triethylamine, carbonate such as potassium carbonate and a catalytic amount of DMAP or in the presence of a source of cyanide, such as acetonecyanohydrin or potassium cyanide.

According to reaction scheme 1, b)necessary diones of the formula I (in which R20, R23, R30and R40means a hydroxy-group) can be obtained, for example, similarly to the method described in Chem. Lett., 1045 (1975), by the esterification of carboxylic acids of the formula XI donovani derivatives of the formula III, IV, V or VI in an inert solvent, for example in a halogenated hydrocarbon, such as dichloromethane, a nitrile, such as acetonitrile, or an aromatic hydrocarbon, such as toluene, in the presence of a base, such as alkylamine, such as triethylamine, and agent combinations, for example 2-chloro-1-methylpyridinium. Depending on the solvent, the esterification is carried out at a temperature of 0 to 110°With education first, as described for option a), some the tion of ester of the formula I, which can be subjected to isomerization, as described for option a), for example, in the presence of a base and catalytic amounts of DMAP or in the presence of a source of cyanide with obtaining the required deanovich derivatives of the formula I (in which R20, R23, R30and R40means a hydroxy-group).

The compounds of formula I in which Q represents a group of Q5may be obtained in accordance with reaction scheme 2 by the method described, for example, in the Synthesis 301 (1991), ibid. 793 (1988) or Tetrahedron 32, 3055 (1976), interaction β-diketonato derivative of formula XII with carbon disulfide in the presence of a base such as a carbonate, such as potassium carbonate, metal hydride such as sodium hydride, or potassium fluoride on aluminum, and an alkylating agent of the formula XIII, in which X1means a leaving group, for example halogen, such as iodine, bromine or primarily chlorine, R25OSO2O, CH3SO2Or. This reaction is preferably carried out in a solvent, for example in amide, such as N,N-dimethylformamide (DMF), a sulfoxide, such as dimethylsulfoxide (DMSO), or a nitrile, such as acetonitrile. The resulting retentional formula XIV is subjected to cyclization using hydroxylamine hydrochloride in the presence of a base, for example sodium acetate, rastvoritele, for example in an alcohol, such as ethanol, or in a simple ether, such as tetrahydrofuran, receiving the compound of the formula Ie, in which Z means S-. The cyclization reaction is carried out at temperatures from 0 to 100°C. the Compound of formula Ie (Z signifies S) if necessary, you can oxidize in accordance with standard methods using, for example, perkiset, such as meta-chloroperbenzoic acid (m-HPBC) or peracetic acid to give the corresponding sulfones and sulfoxidov formula Ie (Z is SO or SO2-), the degree of oxidation of the sulfur atom (Z is SO or SO2-) can be adjusted using an oxidizing agent in an appropriate amount.

Oxidation to compounds of formula Ie (Z is SO or SO2-) carried out by the method described, for example, " House, "Modern Synthetic Reactions", published by W.A. Benjamin, Inc., Menlo Park, California, 1972, c. 334-335 and 353-354.

Activated derivatives of carboxylic acids of the formula II, which is shown in the reaction scheme 1 (a)) and in which X denotes a leaving group, for example halogen, such as bromine, iodine or primarily chlorine, can be obtained according to known standard methods, for example by the method described in C. Ferri, "Reaktionen der organischen Synthese", published by Georg Thieme Verlag, Stuttgart, 1978, S. 461 and forth, and presents the following reaction scheme 3.

With the according to reaction scheme 3, the compounds of formula II, in which X denotes a leaving group, or the formula II in which X signifies halogen, receive, for example, using a halogenation agent, such as thionylchloride, such as thionyl chloride or bromide, phosphorus halide or oxychloride phosphorus, such as pentachloride phosphorus or phosphorus oxychloride or pentabromide phosphorus or phosphorylated, or oxaliplatin, such as oxacillin, or by using intended for formation of the activated complex ester reagent, for example N,N'-dicyclohexylcarbodiimide (DCC) or N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide (EDC) formula X. the compound of formula X used as the halogenation agent, X means, for example, a leaving group, for example halogen, such as fluorine, bromine or iodine and especially chlorine, and W1means, for example, PCl2, SOCl, SOBr or ClCOCO.

The reaction is optionally carried out in an inert organic solvent, such as aliphatic, halogenated aliphatic, aromatic or halogenated aromatic hydrocarbon, such as n-hexane, benzene, toluene, xylenes, dichloromethane, 1,2-dichloroethane or chlorobenzene, at temperatures between -20°With temperatures of distillation of the reaction mixture, preferably at a temperature of from 40 to 150°and in the presence of catalytic amounts of N,N-dimethylformamid the and. Such reactions are in principle known and described in the literature for various values of the leaving group X.

Compounds of formulas III, IV, V and VI are known and can be obtained analogously to the methods described, for example, in WO 92/07837, DE 3818958, EP 0338992 and DE 3902818.

The compounds of formula XII, shown in reaction scheme 2, can be obtained by standard methods, for example, from corresponding compounds of formula II

in which R and m have the above for formula I value, and X denotes a leaving group such as halogen, for example by condensation of Clausena, or from compounds of formula II interaction with salt ketocarboxylic acids of the formula XV

in which R36is indicated for the formula I value, and M+means alkali metal ion (see, for example, WO 96/26192).

Compounds of formulas II and XI are known and can be obtained analogously to the methods described, for example, in WO 97/46530, Heterocycles, 48, 779 (1998), Heterocycles, 46, 129 (1997) or in Tetrahedron Letters, 1749 (1998).

All other compounds of formula I, functionalized in accordance with the definition of the group (R)myou can get various well-known standard methods, for example by alkylation, halogenoalkanes, acylation, amidation, aksamitowana, oxidation and restore it, but the choice of IU the ode receive is determined by the properties (reactivity) of the substituents in the corresponding intermediate compounds. Examples of such reactions are given in WO 97/46353.

All other compounds falling under the General formula I, can be obtained by a simple method taking into account the chemical properties of pyridyl and residues Q.

The final products of formula I can be distinguished by standard methods by concentration or evaporation of the solvent and purify by recrystallization or by rubbing the solid residue in solvents in which it is practically not soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, distillation or column chromatography using acceptable eluent.

In addition, the person skilled in the art can easily determine optimum sequence for some reactions in order to avoid possible further reactions.

If the synthesis is not aimed at obtaining and allocating directly to the pure isomers, the final product may be represented as a mixture of two or more isomers. Such isomers can be separated according to methods that are known per se.

Examples retrieve

Example P1: Obtain 4-hydroxy-3-(2-methyl-6-triptorelin-3-carbonyl)bicyclo[3.2.1]Oct-3-EN-2-it

of 6.68 g (0,0305 mole) methyl ester of 2-methyl-6-triftormetilfosfinov acid (obtained according to the method described in Heterocycles, 46, 129 (1997)) are dissolved in 250 ml of methanol/water is (in a mixture of 3:1) and 22° With portions added 1.92 g (0,046 mole) of hydrate of lithium hydroxide. After exposure for 4 h at 22°the reaction mixture was added to ethyl acetate and 2n. hydrochloric acid, the organic phase is washed three times with water, dried over sodium sulfate and concentrated by evaporation, then the residue triturated with a small amount of hexane. After filtering receive 5,69 g (90% of theory) of the target 2-methyl-6-triftormetilfosfinov acid with a melting point 147-149°C.

This is obtained 2-methyl-6-triftormetilfosfinov acid (2.0 g, 0,0098 mol) was dissolved in 20 ml of oxalicacid. Next, add three drops of dimethylformamide and the mixture for 1 h refluxed. The mixture is then concentrated on a rotary evaporator and the residue (i.e. 2-methyl-6-triftoratsetofenona) dissolved in 30 ml of methylene chloride. After that, when 0°add 2.7 ml (0,0196 mole) of triethylamine and 0.12 g (0,00098 mole) of dimethylaminopyridine, and then added dropwise 1,49 g (0,0108 mol) bicyclo[3.2.1]Oct-2,4-dione, dissolved in 20 ml of methylene chloride. After exposure for 3 h at 22°the reaction mixture is extracted by shaking 2n. the hydrochloric acid. Separated methylenchloride phase is washed with water and then extracted by shaking 10%aqueous solution of sodium bicarbonate, dried over sodium sulfate and concentrate pariani the m The result 3,18 g (100% of theory) 4-oxo-bicyclo[3.2.1]Oct-2-ene-2-silt ether 2-methyl-6-triftormetilfosfinov acid in the form of oil, which can be used in subsequent reactions without further purification.

to 3.02 g (0,0093 mole) 4-oxobicyclo[3.2.1]Oct-2-ene-2-silt ether methyl-6-triftormetilfosfinov acid and 1.9 ml (0,0136 mol) of triethylamine are dissolved in 45 ml of acetonitrile. Then, at 22°With added 0.01 ml of acetonecyanohydrin. After exposure for 18 h at 22°the reaction mixture is poured into a mixture of water with 2n. hydrochloric acid and extracted by shaking with ethyl acetate. An ethyl acetate phase is washed with water and then brine, dried over sodium sulfate and concentrated by evaporation, then the residue is dissolved in a small amount of warm acetone. The desired product crystallizes from the reaction mixture when it is standing. After filtering receive 0,99 g (33% of theory) of the desired 4-hydroxy-3-(2-methyl-6-triptorelin-3-carbonyl)bicyclo[3.2.1]Oct-3-EN-2-it is in the form of white crystals (tPL75-77°).

Example P2: (5-cyclopropyl-3-methylsulfonylamino-4-yl)-(2-methyl-6-triptorelin-3-yl)methanon

14.8 g (0,080 mol) tert-butyl ether 3-cyclopropyl-3-oxopropionate acid are dissolved in 25 ml Meon and type of 1.93 g (0,080 mole) of magnesium. Then, while cooling in an ice bath is added dropwise 7 the l of carbon tetrachloride and to complete the reaction, the reaction mixture was stirred at 22° C for 1 h After concentration by evaporation, the residue is suspended in 100 ml of acetonitrile and 22°With added dropwise to 16.31 g (0,073 mole) of 2-methyl-6-triftormetilfullerenov (obtained according to example P1), dissolved in 50 ml of acetonitrile. After exposure for 6 h, the reaction mixture was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution. Separated an ethyl acetate phase is washed with water, dried over sodium sulfate and concentrated by evaporation. The residue is dissolved in 160 ml of methylene chloride and 22°With added dropwise 10 ml triperoxonane acid. After exposure for 18 h, the reaction mixture was poured into water and extracted with methylene chloride. Methylenchloride phase is washed with water and then brine, dried over sodium sulfate and concentrated by evaporation. The result is 17.3 g (88% of theory) 1-cyclopropyl-3-(2-methyl-6-triptorelin-3-yl)propane-1,3-dione in the form of oil, which can be used in subsequent reactions without further purification.

This is obtained 1-cyclopropyl-3-(2-methyl-6-triptorelin-3-yl)propane-1,3-dione (15.0 g, by 0.055 mole) is dissolved in 150 ml of dimethylformamide and at 0°With portions add 50 g of potassium fluoride on alumina (Alox) as a carrier (0,0055 mol/g, 0,276 mol). After 5 min add 6.7 g (0,088 mole) of carbon disulfide. After soaking in the tip is of 2 hours and added dropwise to 23.6 g (0,166 mole) of methyliodide and the reaction mixture was kept with heating at 22° C. After 2 h Alox filtered off, the filtrate is poured into water and extracted by shaking with ethyl acetate. An ethyl acetate phase is washed with water and then brine, dried over sodium sulfate and concentrated by evaporation. The remainder chromatographic on silica gel (eluent: ethyl acetate/hexane in the ratio 15:1). This way obtain 12.0 g (60% of theory) of 2-(biomedicalengineering)-1-cyclopropyl-3-(2-methyl-6-triptorelin-3-yl)propane-1,3-dione in the form of solids.

12.0 g (0,033 mole) of the product together with a 5.4 g (of 0.066 mole) of anhydrous sodium acetate are suspended in 120 ml of ethanol. Next add 4.6 g (of 0.066 mol) of hydroxylamine hydrochloride and the mixture for reaction incubated at 22°C for 5 hours After that add another 2.7 g of anhydrous sodium acetate and 2.3 g of hydroxylamine hydrochloride. After exposure for 18 h, the reaction mixture was diluted with water and extracted with ethyl acetate. An ethyl acetate phase is washed with water and then brine, dried over sodium sulfate and concentrated by evaporation. In the trituration with a small amount of ethyl acetate to obtain 9.0 g (79,5%) of the desired product as white crystals (tPL103-104°).

Example P3: (5-cyclopropyl-3-methylsulfonylamino-4-yl)-(2-methyl-6-triptorelin-3-yl)methanon

1.50 g (0,0043 mole) (5-cyclopropyl-3-methylsulfanyl Sasol-4-yl)-(2-methyl-6-triptorelin-3-yl)methanone dissolved in 30 ml of acetone/water (mixture 2:1) and 22° With added in several portions of 1.02 g (0,0048 mole) of metaperiodate sodium. After exposure for 5 h, the reaction mixture is concentrated by evaporation on a rotary evaporator. The residue is dissolved in water and ethyl acetate. An ethyl acetate phase is dried over sodium sulfate and concentrated by evaporation. The remainder chromatographic on silica gel (eluent: ethyl acetate/hexane in the ratio 3:1). This way obtain 0.8 g (51%) of the desired product as white crystals (tPL96-97°).

Example P4: Obtain 3-hydroxy-4,4-dimethyl-2-(2-methyl-6-triptorelin-3-carbonyl)cyclohex-2-Aenon (A2-In 24)

of 6.68 g (0,0305 mole) methyl ester of 2-methyl-6-triftormetilfosfinov acid (obtained according to the method described in Heterocycles, 46, 129 (1997)) are dissolved in 250 ml of methanol/water (mixture 3:1) and at a temperature of 22°With portions added 1.92 g (0,046 mole) of hydrate of lithium hydroxide. After exposure for 4 h at 22°the reaction mixture was added to ethyl acetate and 2n. hydrochloric acid, the organic phase is washed three times with water, dried over sodium sulfate and concentrated by evaporation, then the residue triturated with a small amount of hexane. After filtering receive 5,69 g (90% of theory) of the target 2-methyl-6-triftormetilfosfinov acid with a melting point 147-149°C.

This is obtained 2-methyl-6-triftormetilfosfinov acid (1,026 g of 0.005 mol) was dissolved in 20 ml is calilfornia. Next, add three drops of dimethylformamide and the mixture for 1 h refluxed. The mixture is then concentrated by evaporation on a rotary evaporator and the residue (i.e. 2-methyl-6-triftoratsetofenona) dissolved in 100 ml of methylene chloride. After that, when the temperature 0°add 1.6 ml (0,0115 mole) of triethylamine and 0.7 g (0,005 mol) of 4,4-dimethylcyclohexane-1,3-dione. After exposure for 2 h at a temperature of 22°the solvent is removed on a vacuum rotary evaporator, the resulting residue is dissolved in 55 ml of acetonitrile and to rearrange the intermediate product is added 0.15 ml (0,0016 mole) of acetonecyanohydrin and 0.79 ml (0,0057 mole) of triethylamine. After stirring for four hours at room temperature the reaction solution is concentrated by evaporation. The resulting syrup chromatographic on silica gel. Light yellow viscous oil obtained by elution with a mixture of toluene, ethanol, dioxane, triethylamine, and water (in the ratio of 100:40:20:20:5 parts by volume) (Rf=0.39, with the use of this mixture as the mobile phase), dissolved in dichloromethane and successively washed with 75 ml of 5%hydrochloric acid and 75 ml of water. After drying the organic solution over Na2SO4and konventirovaniya by evaporation gain of 1.05 g (63%) of the net specified in the connection header.

H-NMR (d6-DMSO, δ frequent./million): 1,342, s, 6H; putting on 2,088, t, J=9 Hz, 2H; 2,685, s, 3H; 2,982, t, J=9 Hz, 2H; 8,030, d, J=8,1 Hz, 1H; 8,094, d, J=8,1 Hz, 1H.

Example P5: Obtain 5-methyl-5-cryptometrics-1,3-dione (example V)

0.64 g of sodium are placed in 40 ml of ethanol, then add 3,23 ml of methyl ester of acetic acid and 4.9 g of isopropyl ether 4,4,4-Cryptor-3-methylbut-2-ene acid and the mixture was kept at boiling temperature for 18 hours After extraction with diluted hydrochloric acid in countercurrent ethyl acetate the mixture is concentrated by evaporation. The resulting residue is in the form of the crude methyl ester of 2-methyl-4,6-dioxo-2-triftormetilfullerenov acid etherification at boiling point in the presence of 9.1 g of sodium hydroxide in a mixture of methanol and water. After that, the mixture is acidified with hydrochloric acid and extracted with fresh ethyl acetate. After recrystallization from ethyl acetate) to obtain pure 5-methyl-5-cryptometrics-1,3-dione with a melting point of 150-152°C.

Example P6: obtain the methyl ester of 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohexa-2-inkarbaeva acid (V)

Prepare a 30%solution 35,8 g methanolate sodium in 65 ml of dimethyl sulfoxide and within 20 min process at a temperature of 30-35°With a mixture of 16.7 g of 3-methyl-3-butene-2-she and 32.4 g of dimethyl ether of methoxymethanol acid. the alley the mixture is stirred for 1 h at a temperature of 35° C, acidified with hydrochloric acid and then extracted several times with dichloromethane. The organic phase is washed with water, dried and concentrated. By crystallization from hot ethyl acetate and hexane get pure methyl ester of 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohexa-2-inkarbaeva acid with a melting point 117-117,5°C.

Example P7: obtain the methyl ester of 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-triptorelin-3-carbonyl)-4-oxocyclohexa-2-inkarbaeva acid (A2-V)

2,23 g fresh 2-methyl-6-triftormetilfullerenov added to a mixture of 2.14 g of methyl ester of 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohexa-2-inkarbaeva acid and 2.02 g of triethylamine in 30 ml of acetonitrile. After about 30 min add 0,065 g of potassium cyanide and the mixture is stirred for 18 hours the mixture is Then extracted at pH 2 water backflow ethyl acetate, dried over magnesium sulfate and concentrated by evaporation. As a result of filtration through silica gel (mobile phase: ethyl acetate/methanol/triethylamine in the ratio of 85:10:5) pure methyl ester of 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-triptorelin-3-carbonyl)-4-oxocyclohexa-2-inkarbaeva acid in the form of a viscous oil.

Example P8: Obtain 3-hydroxy-4-methoxy-6-methyl-2-(2-methyl-6-triptorelin-3-carbonyl)cyclohex-2-Aenon (A2-V)

0,586 g hydroxide CA is s added to 1.4 g of methyl ester of 2-hydroxy-1-methoxy-5-methyl-3-(2-methyl-6-triptorelin-3-carbonyl)-4-oxocyclohexa-2-inkarbaeva acid in dioxane/water (5:3), and the mixture is stirred for 3 hours The mixture is then acidified (pH 3) and extracted with fresh ethyl acetate. The crude product is purified by chromatography analogously to example P7. Thus obtained 3-hydroxy-4-methoxy-6-methyl-2-(2-methyl-6-triptorelin-3-carbonyl)cyclohex-2-Aenon in the form of a viscous oil (in the form of a mixture of 3 tautomeric forms according to the1H-NMR).

In the manner described above can also be obtained are presented in the following table to connect using for this purpose the methods described in the notes to the General reaction schemes 1 and 2 and in the above-mentioned nastojashem the description of the literature. The following tables Ph means phenyl group, and SS means atenolol group.

Compounds of formulas 2.1 and 2.3-s known under the names of imazamox, imazethapyr, imazighen, imazapyr, dimethenamid, atrazine, terbutylazine, Simazine, terbutryn, cyanazine, ametrine is high, terbumeton, prohexadione-calisi, sethoxydim, clethodim, tepraloxydim, flumetsulam, metosulam, peridot, bromoxynil, ioxynil, sulcotrione, carfentrazone, sulfentrazone, isoxaflutole, glufosinate, primisulfuron, prosulfuron, rimsulfuron, halosulfuron, nicosulfuron, ethoxysulfuron, flazasulfuron and thifensulfuron and described in the Pesticide Manual, 11th ed., published by British Crop Protection Council, 1997, under the numbers 412, 415, 414, 413, 240, 34, 692, 651, 693, 168, 20, 691, 595, 648, 146, 49, 339, 495, 626, 88, 425, 664, 112, 665, 436, 382, 589, 613, 644, 389, 519, 287, 325 and 704. The compound of formula 2.13, in which Y1, Y3and Y4mean Metin, Y2means C-I, R74means COOMe, Y5means nitrogen, Y6means methyl, and Y7means a methoxy group, known under the name of iodosulfuron (primarily in the form of sodium salt) from AGROW No. 296, January 16, 1998, S. 22. The compound of formula 2.13, in which Y1, Y2, Y3and Y4mean Metin, R74means trifluoromethyl, Y5means nitrogen, Y6oz ACHAT trifluoromethyl, and Y7means a methoxy group, known under the name of tritosulfuron and described in DE-A 4038430. The compound of formula 2.13, in which Y1means NH-CHO, Y2, Y3and Y4mean Metin, R74means CONMe2, Y5means Metin, a Y6and Y7means a methoxy group, described for example in WO 95/29899.

S-enantiomer of the compounds of formula 2.12 registered under CAS reg. No. [35597-44-5]. The compound of General formula 2.2, i.e. aRS,1'S(-)N-(1'-methyl-2'-methoxyethyl)-N-chloroacetyl-2-ethyl-6-methylaniline, and the compound of General formula 2.3, i.e. the (1S,aRS)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)ndimethylacetamide described, for example, in WO 97/34485. The compound of formula 2.9, in which R69means NO2, known by the name Metatron ipiano, for example, in US 5006158. The compound of formula 2.6, in which R62means ethoxypropan, R63means fluorine, Y means Metin, R64means methoxycarbonyl, R65means hydrogen, and R66means chlorine, known under the name of caruncular, for example, from AGROW No. 261, August 2, 1996, S. 21. The compound of formula 2.6, in which R62means a methoxy group, R63means hydrogen, Y represents C-F, R64means fluorine, R65means hydrogen, and R66means fluorine, known under the name of florasulam and described in US 5163995.

In addition, the following connections, who may be included in the offer in the invention compositions, described in the Pesticide Manual, 11th ed., published by British Crop Protection Council, 1997:

The compound of formula (name)No. in the Pesticide Manual, 11th ed.
2.14 (metribuzin)497
2.15 (klonipin)8
2.16 (glyphosate)383
2.17 (bentazon)65
2.18 (pendimethalin)557
2.19 (dicamba)210
2.20 (butyl)100
2.22 (clomazone)150
2.23 (2,4-D)192
2.24 (flumiclorac)340
2.25 (fluthiacet-methyl)359
2.26 (floortime)356
2.27 (flumioxazin)341
2.28 (paraquat)550
2.29 (azafenidin)37
2.30 (flutamide)51
2.33 (sulfosate)383
2.34 (Azul)33
2.35 (norflurazon)526

The compound of formula (name)No. in the Pesticide Manual, 11th ed.
2.36 (terbacil)689
2.37 (easier) 702
2.38 (dithiopyr)259
2.39 (hexazinone)400
2.40 (Diuron)260
2.41 (2M-4, MSRA)455
2.42 (mecoprop)459
2.43 (tebuthiuron)683

The compound of formula 2.7, in which R67means hydrogen, and a method thereof are described in US 3790571, and the compound of formula 2.6, in which R62means ethoxypropan, Z denotes a nitrogen, R63means fluorine, R64means chlorine, R65means hydrogen, and R66means chlorine, described in US 5498773. The compound of formula 2.21 and method thereof are described in US 5183492, and the connection formula 2.22 known by the name isoxaflutole and described in AGROW No. 296 dated January 16, 1998, S. 22. the compound of formula 2.31 known by the name phentramin and described in the proceedings of the conference on the protection of agricultural crops "The 1997 British Crop Protection Conference - Weeds", so 1, 2-8, c. 67-72, while the compound of the formula 2.32 known under the name of JV 485 (isocaproate) and described in the proceedings of the conference on the protection of agricultural crops "The 1997 British Crop Protection Conference - Weeds", so-1, 3A-2, c. 93-98. The compound of formula 2.44 known by the name pethoxamid and described, for example, in EP-A 0206251. The compound of formula 2.45 known by the name of procarpet and described, for example, in EP-A 0507171, and the connection formula 2.46 known by the name flatlet and described, for example, in US 5530126. The compound of formula 2.47 known under the name of cynodon-ethyl and described, for example, in DE-A 4037840. The compound of formula 2.48 known by the name bestindian and described, for example, in WO 97/08953. The compound of formula 2.49 known under the name of diflubenzuron and described, for example, in EP-A 0646315. The compound of formula 2.50 (nicarbazin) and the method thereof is described in DD 298393 and US 5194085. The compound of formula 2.51 (flutter-ethyl) described in Abstracts of Papers American Chemical Society, 2000, T. 220, part 1, c. AGRO 174.

With the invention it has been unexpectedly found that the effect of the application of the combination of the active ingredient of formula I with one or more active ingredients from among the compounds of formulae 2.1 to 2.51 exceeds in weed control total effect, which in principle would be expected from the use of such active ingredients separately, due to the spectrum of each of these individual active ingredients extends primarily from the following two aspects. The first one is to reduce the consumption rates of the individual compounds of formulas I and 2.1-2.51, while maintaining their actions at a sufficiently high level, and the second is that proposed in the invention composition W is employed, with high efficiency to combat weeds even in those cases, when the application of the individual compounds in small doses is impractical and inefficient from agronomic point of view. In the result it is possible to considerably broaden the spectrum of weeds that need to fight, and further improve the selectivity in crops of useful plants, which is a necessary condition for unintentional overdose of the active ingredient. Proposed in the invention composition not only provides a highly efficient destruction of weeds in crops of useful plants, but also provides more freedom of choice of crops to be grown later in the same areas.

Proposed in the invention composition can be used to combat a wide range of agronomically important weeds, such as Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica. The composition according to the invention permits its use in all methods commonly used in agriculture, and, in particular, suitable for predsjedava processing, post-harvest processing and handling of seeds. Proposed in the invention is a composition suitable for control of weeds, especially in crops still is useful plants, as cereals, rape, sugar beet, sugar cane, plantation crops, rice, maize and soybean, as well as for selective weed control. Under the "cultures" in the context of the present invention are also culture, which as a result of conventional methods of breeding or genetic engineering was developed tolerance to herbicides or whole classes. In the present invention it is also proposed a method of combating the growth of unwanted plants in crops of useful plants, namely, that a cultivated plant or place of its growth process herbicide effective amount of the composition according to the invention.

Proposed in the invention composition contains a mixture of active ingredient of formula I and the active ingredients of formulae 2.1 to 2.51 in any ratio between these components, but usually one of these components is present in excess relative to the other components. In General, the ratio in the mixture (by mass) between the active ingredient of formula I and other components of the mixture, which are compounds of formulae 2.1 to 2.51, is from 1:2000 to 2000:1, mainly from 200:1 to 1:200. The rate can vary within wide limits and depends on the nature and properties of soil, method of treatment (pre - or post-harvest processing, etching SEM is h, the introduction into the seed furrow, the processing is not cultivated land etc), cultivated plants, weeds, which compete prevailing in some areas climatic conditions and other factors, as determined by the method of processing, the processing time and the target crop. Norm of expenditure proposed in the invention a mixture of the active ingredients can usually be from 1 to 5000 g of a mixture of active ingredients per hectare. A mixture of the compounds of formula I with the compounds of formulae 2.1 to 2.51 can be used in unmodified form, i.e. as they are the result of synthesis. More preferably, however, process them according to conventional methods, together with auxiliary substances commonly used in cooking techniques preparative forms, such as solvents, solid carriers, or surface-active substances, obtaining, for example, mulgirigala concentrates, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, Farrukh Dustov, granules or microcapsules. Processing methods, such as spraying, treatment in the form of mists (atomized spraying, dusting, dressing, scattering or watering, as well as the type of drug chosen in accordance with the objectives and preve is youdemi circumstances.

Preparative form, i.e. the compositions, compounds or mixtures containing the compound (active ingredient) of formula I and 2.1-2.51 and usually one or more solid or liquid auxiliary substances (adjuvants)used in the preparation technology preparative forms, get a known method, for example by homogeneous mixing and/or grinding the active ingredients with adjuvants, for example solvents or solid carriers. In addition, when receiving preparative forms optionally, you can use surface-active substances (surfactants).

Examples of solvents and solid carriers are described, for example, in WO 97/34485 on page 6.

As surface-active substances depending on what should be included in formulations of the active ingredient of the formula I use nonionic, cationogenic and/or anionic surfactants and mixtures of surfactants with high emulsifying, dispersing and wetting properties.

Examples suitable for this purpose anionic, nonionic and cationogenic surfactants are described in particular in WO 97/34485 on page 7 and 8.

In addition, to obtain the proposed invention herbicide compositions suitable also commonly used in cooking techniques preparative forms of surfactants, which are described in particular in "Mc Cutcheon''s Detergents and Emulsifiers Annual", published by MC Publishing Corp., Ridgewood New Jersey, 1981, The Stache, H., "Tensid-Taschenbuch", publishing house Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash, "Encyclopedia of Surfactants", so I-III, published by Chemical Publishing Co., New York, 1980-81.

Usually herbicide formulations contain from 0.1 to 99 wt.%, especially from 0.1 to 95 wt.%, the mixture of active ingredients containing compound of the formula I and the compounds of formulae 2.1 to 2.51, from 1 to 99.9 wt.% solid or liquid excipients included in the formulation, and from 0 to 25 wt.%, first of all, from 0.1 to 25 wt.%, Surfactant.

If included in the sale of products is generally preferable compounds or compositions in the form of concentrates, the end user typically uses diluted preparations. These preparations may also contain other additives, such as stabilisers, for example vegetable oils or epoxydecane vegetable oil (epoxydecane coconut oil, rapeseed oil or soybean oil), antispyware, for example silicone oil, preservatives, viscosity regulators, binders, adhesives, as well as fertilizers or other active substances. The preferred preparative forms have the following composition (% = wt.%).

Mulgirigala concentrates:
the mixture of active ingredients:1-90%, preferably 5-20%
Surfactants:1-30%, PR is doctitle 10-20%
carrier liquid:5-94%, preferably 70-85%
Dusty:
the mixture of active ingredients:0.1 to 10%, preferably 0.1 to 5%
solid carrier:of 99.9 to 90%, preferably about 99.9 to 99%
Suspension concentrates:
the mixture of active ingredients:5-75%, preferably 10-50%
water:94-24%, preferably 88-30%
Surfactants:1-40%, preferably 2-30%
Wettable powders:
the mixture of active ingredients:0.5 to 90%, preferably 1-80%
Surfactants:0.5 to 20%, preferably 1-15%
solid carrier:5-95%, preferably 15-90%
Pet:
the mixture of active ingredients:0.1 to 30%, preferably 0.1 to 15%
solid carrier:of 99.5 to 70%, preferably 97-85%

Below the invention is illustrated in the examples, not limiting its scope.

F1. Mulgirigala concentratesa)b)in)g)
see the camping active ingredients 5%10%25%50%
dodecylbenzenesulfonate calcium6%8%6%8%
polyglycidyl ether of castor oil (36 moles of ethylene oxide)4%-4%4%
polyglycolic ether op (7-8 moles of ethylene oxide)-4%-2%
cyclohexanone--10%20%
the mixture arene. hydrocarbon, C9-C1285%78%55%16%
Such concentrates can be obtained emulsions of any desired concentration by dilution with water.
F2. Solutionsa)b)in)g)
the mixture of active ingredients5%10%50%90%
1-methoxy-3-(3-methoxypropane)propane-20%20%-
polyethylene glycol 400 MM20%10%--
N-methyl-2-pyrrolidone--30% 10%
the mixture arene. hydrocarbon, C9-C1275%60%--
Such solutions are suitable for use in the form of microdrops.
F3. Wettable powdersa)b)in)g)
the mixture of active ingredients5%25%50%80%
sodium lignosulphonate4%-3%-
sodium lauryl sulfate2%3%-4%
diisobutyldimethoxysilane sodium-6%5%6%
polyglycolic ether op (7-8 moles of ethylene oxide)-1%2%-
highly dispersed silicic acid1%3%5%10%
kaolin88%62%35%-

The active ingredient is mixed to homogeneity with auxiliary substances and the resulting mixture is thoroughly ground in a suitable for this purpose mill, receiving wettable powders, which is can be diluted with water to obtain suspensions of any desired concentration.

F4. Granules coateda)b)in)
the mixture of active ingredients0,1%5%15%
highly dispersed silicic acid0,9%2%2%
inorganic media (⊘ 0,1-1 mm), such as CaCO3or SiO299,0%93%83%
The active ingredient is dissolved in methylene chloride and spray applied to the carrier, after which the solvent is evaporated in vacuum.
F5. Granules coateda)b)in)
the mixture of active ingredients0.1%5%15%
polyethylene glycol 200 MM1,0%2%3%
highly dispersed silicic acid0,9%1%2%
inorganic media (⊘ 0,1-1 mm), such as CaCO3or SiO298,0%92%80%
The finely ground active ingredient is uniformly applied, in a mixer on medium moistened with polyethylene glycol. In this way p is get a dust free granules coated.
F6. Extruded granulesa)b)C) d)
the mixture of active ingredients0,1%3%5% 15%
sodium lignosulphonate1,5%2%3% 4%
carboxymethylcellulose1,4%2%2% 2%
kaolin97,0%93%90% 79%
The active ingredient is mixed and milled with auxiliary substances and the resulting mixture is moistened with water. Then this mixture ekstragiruyut and then dried in the air stream.
F7. Dustya)b)in)
the mixture of active ingredients0,1%1%5%
talc39,9%49%35%
kaolin60,0%50%60%

Ready-to-use dusty obtained by mixing the active ingredient with the carriers and grinding the mixture in suitable for this purpose mill.

the mixture of active ingredients
F8. Suspension concentratesa)b)in)g)
3%10%25%50%
ethylene glycol5%5%5%5%
polyglycidyl ether of Nonylphenol (15 moles of ethylene oxide)-1%2%-
sodium lignosulphonate3%3%4%5%
carboxymethylcellulose1%1%1%1%
37%aqueous formaldehyde solution0,2%0,2%0,2%0,2%
silicone oil emulsion0,8%0,8%0,8%0,8%
water87%79%62%38%

The finely ground active ingredient is mixed to homogeneity with auxiliary substances, receiving a suspension concentrate from which the dilution water can be obtained suspensions of any desired concentration.

In practice it is often more expedient separately prepare the formulations based on the compounds of formula I and the component or components of a mixture of formulae 2.1 to 2.51 and then shortly before use to combine these compounds in water in sootvetstvuuschem device for processing in the desired proportions to obtain the so-called "tank mixtures".

Biological examples

A synergistic effect is seen in the case when the action of the combination of active ingredients, i.e. compounds of formulas I and 2.1-2.51, exceeds the total effect can be achieved with the use of each of the active ingredients separately.

Expected herbicide action We for a given combination of two herbicides can be calculated by the formula below Colby (see S.R. COLBY, "Calculating synergistic and antagonistic response of herbicide combinations", Weeds 15, cc. 20-22, 1967):

We=X+[Y•(100-X)/100],

where

X is expressed as the percentage of herbicide action when processing a compound of formula I with a consumption rate of p kg / ha compared to the untreated control (=0%),

Y is expressed as the percentage of herbicide action when processing a compound of formulae 2.1 to 2.51 at a rate of flow q kg per hectare compared to the untreated control,

We expected herbicide action (herbicide action in percentage of untreated control) in the treatment of compounds of formulas I and 2.1-2.51 when the rate of application of p+q kg of active ingredient per hectare.

When in fact the observed action exceeds the expected value We place a synergistic effect.

The presence of a synergistic effect when using the compounds of formula I in combination with the compounds of formulae 2.1 to 2.51 confirmed by the following examples.

OPI is the W of the experiment: preschedule action

one - and two pilot plants are sown in plastic pots with regulatory greenhouse-greenhouse soil mixtures. Immediately after sowing by spraying spend processing the test compounds in the form of an aqueous suspension (500 litres of water/ha). Consumption rates depend on the optimal dose determined separately for field and greenhouse conditions. After this pilot plants grown in the greenhouse under optimal conditions. Effect of herbicides on the experimental plants are assessed in 36 days (in %, 100% corresponds to complete loss of plants, 0% corresponds to no phyto-toxic action). Examples confirming the existence sinergeticheskogo effect in the application proposed in the invention compositions, presented in the following tables B1-B6.

The mixture contains as active ingredients a compound of formula a in the number 915 g/l and the compound of formula 3.1 in the amount of 45 g/L.

Table B1
Experienced plantConn. 1.001 [25 g/ha]Mix And

[900 g/ha]
Conn. 1.001 [25 g/ha] + mixture [900 g/ha]We according to Colby
Sorghum30209044
Chenopodium00 1000
Sida07010070

Table B2
Experienced plantConn. 1.001 [12.5 g/ha]Mix And

[900 g/ha]
Conn. 1.001 [12.5 g/ha] + mixture [900 g/ha]We according to Colby
Sorghum0208020
Chenopodium00950
Sida0709570
Table B3
Experienced plantConn. 1.001 [6,25 g/ha]Mix And

[900 g/ha]
Conn. 1.001 [6,25 g/ha] + mixture [900 g/ha]We according to Colby
Sorghum0207020
Chenopodium00950
Sida0709570
Table B4
Experienced plantConn. 1.001 [25 g/ha]Mix And

[300 g/ha]
Conn. 1.001 [25 g/ha] + mixture [300 g/ha]We according To the BBC
Chenopodium00900
Ipomoea30010030
Sida00400
Table B5
Experienced plantConn. 1.001 [12.5 g/ha]Mix And

[300 g/ha]
Conn. 1.001 [12.5 g/ha] + mixture [300 g/ha]We according to Colby
Chenopodium00800
Ipomoea00600
Sida00400
Table B6
Experienced plantConn. 1.001 [6,25 g/ha]Mix And

[300 g/ha]
Conn. 1.001 [6,25 g/ha] + mixture [300 g/ha]We according to Colby
Chenopodium00800
Ipomoea00600
Sida00400

Description of experiment: post-harvest action

Pilot plants are grown in plastic pots in those who personal conditions to the stage of 2-3 leaves. For cultivation as a substrate using normative greenhouse-greenhouse soil mixtures. At the stage of 2-3 leaves of the experimental plants treated with herbicide individually and as a mixture. The processing using aqueous suspension of the test compounds in 500 l of water/ha consumption rates depend on the optimal dose determined separately for field and greenhouse conditions. Effect of herbicides on the experimental plants are assessed in 33 days (in %, 100% corresponds to complete loss of plants, 0% corresponds to no phyto-toxic action). Examples confirming the existence sinergeticheskogo effect in the application proposed in the invention compositions, presented in the following tables B7-B10.

The mixture contains as active ingredients a compound of formula a in the number 915 g/if the connection formulas 3.1 in the amount of 45 g/L.

td align="center"> 100
Table B7:

experience in post-harvest research action
Experienced plantConn. 1.001 [12.5 g/ha]Mix And

[900 g/ha]
Conn. 1.001 [12.5 g/ha] + mixture [900 g/ha]We according to Colby
Ipomoea00800
Polygonum02020
Xanthium80010080
Table B8:

experience in post-harvest research action
Experienced plantConn. 1.001 [12.5 g/ha]Mix And

[300 g/ha]
Conn. 1.001 [12.5 g/ha] + mixture [300 g/ha]We according to Colby
Ipomoea00800
Polygonum00700
Xanthium8009880
Table B9:

experience in post-harvest research action
Experienced plantConn. 1.001 [6,25 g/ha]Mix And

[900 g/ha]
Conn. 1.001 [6,25 g/ha] + mixture [900 g/ha]We according to Colby
Ipomoea00700
Polygonum0207020
Xanthium7008070
Table 10:

experience in post-harvest research action
Experienced plantConn. 1.001 [625 g/ha] Mix And

[300 g/ha]
Conn. 1.001 [6,25 g/ha] + mixture [300 g/ha]We according to Colby
Ipomoea00800
Polygonum00700
Xanthium7007070

The data in the following tables correspond to the data obtained from the assessment of herbicide action in 14 days.

Table B11:

Preschedule action
experienced plantConn. E8 [50 g/ha]Conn. 2.18

[500 g/ha]
Conn. E8 [50 g/ha] + Conn. 2.18 [500 g/ha]We according to Colby
Polygonum50809590
Table B12:

Preschedule action
experienced plantConn. E8 [100 g/ha]Seed [250 g/ha]Suede [100 g/ha] + Conn. 2.14 [250 g/ha]We according to Colby
Polygonum50509075
Table B13:

Preschedule action
experienced plant Conn. E8 [100 g/ha]Conn. 2.14 [125 g/ha]Suede [100 g/ha] + Conn. 2.14 [125 g/ha]We according to Colby
Polygonum50309065

In table B14 connection # a corresponds to the formula 2.13, in which R74means-CH2CH2CF3each of Y1, Y2, Y3and Y4means Metin, Y5means nitrogen, a Y6means methyl.

Table B14:

Preschedule action
Experienced plantConn. E8 [100 g/ha]Conn. A [60 g/ha]Conn. E8 [100 g/ha] + Conn. A [60 g/ha]We according to Colby
Polygonum50809590
Table B15:

Preschedule action
Experienced plantConn. E8 [50 g/ha]Conn. 2.30 [60 g/ha]Conn. E8 [50 g/ha] + Conn. 2.30 [60 g/ha]We according to Colby
Polygonum50309065
Table B16:

Preschedule action
Experienced plantConn. E8 [50 g/ha]Conn. 2.21 [30 hPa] Conn. E8 [50 g/ha] + Conn. 2.21 [30 g/ha]We according to Colby
Polygonum505010075

In table B17 connection # 2.4.a corresponds to the formula 2.4, in which R57means chlorine, R58means ethyl, a R59means tert-butyl.

Table B17:

Preschedule action
Experienced plantConn. E8 [50 g/ha]Conn. 2.4.a [125 g/ha]Conn. E8 [50 g/ha] + Conn. 2.4.a [125 g/ha]We according to Colby
Polygonum50308565
Table B18:

Preschedule action
Experienced plantConn. 1.001 [25 g/ha]Conn. 2.2.b [300 g/ha]Conn. 1.001 [25 g/ha] + Conn. 2.2.b [300 g/ha]We according to Colby
Chenopodium8009580
Solanum80409888
Cyperus00500

In table B19 connection # 2.3.a corresponds to the formula 2.3, in which R56means CH(Me)-CH2OMe.

<>
Table B19:

Preschedule action
Experienced plantConn. 1.001 [12.5 g/ha]Conn. 2.3.a [100 g/ha]Conn. 1.001 [12.5 g/ha] + Conn. 2.3.a [100 g/ha]We according to Colby
Chenopodium80209084
Solanum75609090
Cyperus0206020

In table B20 connection # s corresponds to the formula 2.2, in which R53and R54means ethyl, a R55mean CH2OMe.

Table B20:

Preschedule action
Experienced plantConn. 1.001 [12.5 g/ha]Conn. S [100 g/ha]Conn. 1.001 [12.5 g/ha] +Conn. S [100 g/ha]We according to Colby
Chenopodium80209084
Solanum75509588
Cyperus00300

In table B21 connection # 2.2.d corresponds to the formula 2.2, in which 53means ethyl, R54means methyl, a R55means of CH2O-CH2CH3.

Table B21:

Preschedule action
Experienced plantConn. 1.001 [12.5 g/ha]Conn. 2.2.d [100 g/ha]Conn. 1.001 [12.5 g/ha] + Conn. 2.2.d [100 g/ha]We according to Colby
Solanum75609590
Table B22:

Preschedule action
Experienced plantConn. 1.001 [25 g/ha]Conn. 2.30 [100 g/ha]Conn. 1.001 [25 g/ha] + Conn. 2.30 [100 g/ha]We according to Colby
Cyperus1006010

The data in the following tables correspond to the data obtained from the herbicide actions through 31 days.

In table V connection # 2.4.a corresponds to the compound of formula 2.4, in which R57means chlorine, R58means ethyl, and R59means isopropyl.

Table V:

Preschedule action
Experienced plantConn. 1.001 [25 g/ha]Conn. 2.4.a [250 g/ha] Conn. 1.001 [25 g/ha] + Conn. 2.4.a [250 g/ha]We according to Colby
Polygonum0208020

In the table In 24 connection # 2.4.b corresponds to the compound of formula 2.4, in which R57means chlorine, R59means ethyl, and R58means ethyl.

The table In 24:

Preschedule action
Experienced plantConn. 1.001 [25 g/ha]Conn. 2.4.b [125 g/ha]Conn. 1.001 [25 g/ha] + Conn. 2.4.b [125 g/ha]We according to Colby
Polygonum00400

In table B25 connection # s corresponds to the compound of formula 2.4, in which R57means chlorine, R58means ethyl, a R59means tert-butyl.

Table B25:

Preschedule action
Experienced plantConn. 1.001 [25 g/ha]Conn. S [250 g/ha]Conn. 1.001 [25 g/ha]+ Conn. S [250 g/ha]We according to Colby
Ipomoea7009070
Xanthium80010080

In table V connection # 2.4.d corresponds to the compound of formula 2.4, in which R57means metalcorp, R58means ethyl, and R59means tert-butyl.

Table V:

Preschedule action
Experienced plantConn. 1.001 [25 g/ha]Conn. 2.4.d [250 g/ha]Conn. 1.001 [25 g/ha] + Conn. 2.4.d [250 g/ha]We according to Colby
Ipomoea7008070
Xanthium80109582
Table B27:

Preschedule action
Experienced plantConn. 1.001 [25 g/ha]Conn. 2.14 [125 g/ha]Conn. 1.001 [25 g/ha] + Conn. 2.14 [125 g/ha]We according to Colby
Ipomoea7008570
Xanthium802010084

In table B28 connection # a corresponds to the compound of formula 2.6, in which R62means hydrogen, R63means methyl, R64means fluorine, R65means hydrogen, Y represents nitrogen, Z means Metin, and R66means fluorine.

Table B28:

Preschedule actionExperienced plantConn. 1.001 [50 g/ha]Conn. A [30 g/ha]Conn. 1.001 [50 g/ha] + Conn. A [30 g/ha]We according to ColbyPolygonum0309030

The data in the following tables correspond to the data obtained from the assessment of herbicide action after 21 days.

In table V connection # a corresponds to the compound of formula 2.7, in which R67means-C(O)-S-n-octyl.

Table V:

Post-harvest action
Experienced plantConn. 1.001 [25 g/ha]Conn. A [250 g/ha]Conn. 1.001 [25 g/ha] + Conn. A [250 g/ha]We according to Colby
Ipomoea30108030
Polygonum7509575
Xanthium901010091
Table B30:

Post-harvest action
Experienced plantConn. 1.001 [25 g/ha]Conn. 2.19 [250 g/ha]Conn. 1.001 [25 g/g is] + Conn. 2.19 [250 g/ha]We according to Colby
Ipomoea30609572

Table V:

Post-harvest action
Experienced plantConn. 1.001 [25 g/ha]Conn. 2.16 [360 g/ha]Conn. 1.001 [25 g/ha] + seed [360 g/ha]We according to Colby
Ipomoea30207046
Polygonum75109084
Table V32:

Post-harvest action
Experienced plantConn. 1.001 [12.5 g/ha]Conn. 2.33 [360 g/ha]Conn. 1.001 [12.5 g/ha] + Conn. 2.33 [360 g/ha]We according to Colby
Polygonum3009030

In table V connection # a corresponds to the compound of formula 2.12, in which R73mean NH2.

Table V:

Post-harvest action
Experienced plantConn. 1.001 [25 g/ha]Soeda [400 g/ha]Conn. 1.001 [25 g/ha]+ Conn. 2.33 [400 g/ha] We according to Colby
Ipomoea30209044
Table V:

Post-harvest action
Experienced plantConn. 1.001 [12.5 g/ha]Conn. 2.25 [2 g/ha]Conn. 1.001 [12.5 g/ha]+ Conn. 2.25 [2 g/ha]We according to Colby
Ipomoea3005030
Polygonum3004030

In table V connection # a corresponds to the compound of formula 2.1, in which R52means hydrogen, and R51means ethyl.

Table V:

Post-harvest action
Experienced plantConn. 1.001 [12.5 g/ha]Conn. A [30 g/ha]Conn. 1.001 [12.5 g/ha] + Conn. A [30 g/ha]We according to Colby
Polygonum30307051

In table V connection # 2.1.b corresponds to the compound of formula 2.1, in which R51means of CH2OMe, a R52means hydrogen.

Experienced plant
Table V:

Post-harvest action
Conn. 1.001 [25 g/ha].2.1.b [30 g/ha]Conn. 1.001 [25 g/ha] + Conn. 2.1.b [30 g/ha]We according to Colby
Polygonum75309083

The data in the following tables correspond to the data obtained from the assessment of herbicide action in 23 days.

In table V connection 2.13.b corresponds to the compound of formula 2.13, in which R74means-COOMe, each of Y1, Y2, Y3and Y4means Metin, Y5means Metin and Y6and Y7mean dipterocarp.

Table V:

Preschedule action
Experienced plantConn. 1.001 [6 g/ha]Conn. 2.13.b [15 g/ha]Conn. 1.001 [6 g/ha] + Conn. 2.13.b [15 g/ha]We according to Colby
Chenopodium50709585
Table V:

Preschedule action
Experienced plantConn. 1.001 [6 g/ha]Conn. 2.13.c [60 g/ha]Conn. 1.001 [6 g/ha] + Conn. S [60 g/ha]We according to Colby
Chenopodium501085 55

In table V connection 2.13.d corresponds to the compound of formula 2.13, in which Y1, Y2, Y3and Y4mean Metin, R74means trifluoromethyl, Y5means nitrogen, Y6means trifluoromethyl, a Y7means a methoxy group.

Table V:

Preschedule action
Experienced plantConn. 1.001 [6 g/ha]Conn. 2.13d [7.5 g/ha]Conn. 1.001 [6 g/ha] + Conn. 2.13.d [7.5 g/ha]We according to Colby
Amaranthus10809582

With the invention it has been unexpectedly found that for use in the mixture with the proposed invention is a composition having a synergistic effect, suitable specific antidotes. Therefore, the present invention relates also to compositions selective herbicide steps to fight with the grasses and weeds in crops of useful plants, especially in crops of corn, containing the compound of formula I, one or more compounds from among the compounds of formulae 2.1 to 2.51 and safener (antidote) and protecting useful plants, but not the weeds, from phyto-toxic action of the herbicide, and to the use of such compositions for combating weeds which in crops of useful plants.

According to the invention it is, therefore, proposed composition selective herbicide action, which along with the usual inert excipients used in the preparation technology preparative forms, such as carriers, solvents and wetting agents, as the active ingredient is a mixture of

a) herbicide-synergistic effective amounts of compounds of formula I and one or more compounds from among the compounds of formulae 2.1 to 2.51 and

b) herbicide-antagonistically effective amount of a compound selected from the group comprising the compound of formula 3.1

the compound of formula 3.2

the compound of formula 3.3

the compound of formula 3.4

the compound of formula 3.5

the compound of formula 3.6

the compound of formula 3.7

the compound of formula 3.8

the compound of formula 3.9

the compound of formula 3.10

the compound of formula 3.11

the compound of formula 3.12

and its ethyl ester,

the compound of formula 3.13

the compound of the formula 3.14

the compound of formula 3.15

and the compound of formula 3.16

The present invention relates also to compositions selective herbicide action, which along with the usual inert excipients used in the preparation technology preparative forms, such as carriers, solvents and wetting agents, as the active ingredient is a mixture of

a) herbicide effective amount of the compounds of formula I and

b) herbicide-antagonistically effective amount of compounds selected from compounds of formulae 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 3.10, 3.11, 3.12, 3.13, 3.14, 3.15 and 3.16.

Preferred compositions according to the invention contain as an antidote compound among the compounds of formula 3.1, 3.3 and 3.8. These antidotes are most suitable for use in the composition proposed in the invention compositions, which contain the above-mentioned preferred compounds of formula I and optionally compounds of formulae 2.1 to 2.51.

The most effective songs are, it has been found that combinations of compounds of the formula I with the compound of the formula 3.1, PR is most preferred as the compounds of formula I is compound No. 1.001. Such a composition is preferably used together with the compound of the formula I

The present invention relates also to a method of selective weed control in crops of useful plants, which consists in the fact that the useful plants, seeds or cuttings or area of their cultivation process herbicide effective amount of a herbicide of formula I, optionally, one or more herbicides from among the compounds of formulae 2.1 to 2.51 and herbicide-antagonistically effective amount of a safener of formula 3.1-3.16.

Compounds of formulae 3.1 to 3.16 known and described, for example, in the Pesticide Manual, 11th ed., British Crop Protection Council, 1997, No. 61 (formula 3.1, enoxacin), 304 (formula 3.2, genclerin), 154 (formula 3.3, logintest), 462 (formula 3.4, mefenpyr-diethyl), 377 (formula 3.5, furilazole), 363 (formula 3.8, fluxotine), 213 (equation 3.9, dichlormid) and 350 (equation 3.10, Florasol). The compound of formula 3.11 known under the name MON-4660 (Monsanto company) and is described, for example, in EP-A 0436483.

The compound of formula 3.6 (AU 304415) is described, for example, in EP-A 0613618, and the connection formula 3.7 described in DE-A 2948535. The compounds of formula 3.12 described in DE-A 4331448, and the connection formula 3.13 described in DE-A 3525205. The compound of the formula 3.14 known, for example, from US 5215570, and the connection formula 3.15 known from EP-A 0929543. the compound of formula 3.16 described in WO 99/00020. is beside the compounds of formula 3.16 other 3-(5-tetrachlorocarbon)-2-quinolones described in WO 99/00020, the most suitable for protecting cultivated plants from phyto-toxic action of compounds of the formula I are primarily compounds listed mainly in tables 1 and 2 c. 21-29.

Cultivated plants, protecting them from the adverse effects of the above herbicides can provide antidotes of formulae 3.1 to 3.16 are mainly cereals, cotton, soybeans, sugar beets, sugar cane cultivated on plantations crops, canola, corn and rice, primarily corn. Under "cultivated plants" refers to plants that have the result of conventional methods of breeding or genetic engineering was developed tolerance to herbicides, respectively, to different classes of herbicides.

Weeds that are struggling can be both monocotyledonous and dicotyledonous weed plants such as Stellaria, Agrostis, Digitaria, Avena, Apera, Brachiaria, Phalaris, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Panicum, Bromus, Alopecurus, Sorghum halepense, Sorghum bicolor, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.

To cultivated areas include land already germinated or grown cultivated plants or land already planted these seeds of cultivated plants, as well as soil that is allocated to the cultivation of these cultural RA the plants.

The antidote formula 3.1-3.16, depending on the purpose of application can be used for pre-treatment of seed or planting material of cultivated plants (seed or cuttings) either before or after sealing the seed in the soil. However, the processing of the antidote can be performed individually or together with the herbicide after emergence of the plants. Thus, processing plants or seed antidote in principle can be performed regardless of the time of herbicide treatment. However, plants can be treated and at the same time means both the herbicide and the antidote (for example, when used in the form of a tank mixture). The ratio between the norms of consumption of antidote and herbicide depends on the processing method. For example, when processing fields, which may consist of a tank mix herbicide in combination with a safener, or in separate introduction of safener and herbicide, the ratio between the amount of herbicide and the number of antidote is usually from 100:1 to 1:10, preferably from 20:1 to 1:1. When processing fields, the consumption rate of the antidote, as a rule, is from 0.001 to 1.0 kg/ha, preferably from 0.001 to 0.25 kg/ha

The rate of application of herbicides is usually from 0.001 to 5 kg/ha, preferably, however, 0.005 to 0.5 kg/ha About what abotu proposed in the invention compositions can be made in all conventional agricultural methods, such as predsjedava processing, post-harvest processing and seed treatment. When the seed treatment rate of application of the antidote is usually from 0.001 to 10 g per kg of seed, preferably from 0.05 to 2 g per kg seeds. If the antidote is carried out in liquid form shortly before sowing during the swelling of the seeds, it is advisable to use solutions antidote with the concentration of the active ingredient from 1 to 10000, preferably from 100 to 1000 ppm million

To handle the antidotes of formulae 3.1 to 3.16 or such antidotes in combination with a herbicide of formula I and optionally with one or more herbicides from among compounds 2.1-2.51 advisable to recycle together with usually used in cooking techniques preparative forms of auxiliary substances to ensure that proper preparations, for example mulgirigala concentrates, pastes for obmazyvanija, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, Farrukh Dustov, granules or microcapsules.

Such formulation are described, for example, in WO 97/34485 on p.9-13. Such formulations of get known method, for example by homogeneous mixing and/or grinding the active ingredients with liquid or solid excipients used in the composition p is reparativnyh forms, for example solvents or solid carriers. In addition, when receiving preparative forms optionally, you can use surface-active substances (surfactants). Examples suitable for this purpose solvents and solid carriers are described, for example, in WO 97/34485 on p.6.

As surface-active substances depending on what should be included in formulations of compounds of formula I, 2.1-2.51 and 3.1-3.16 use of nonionic, cationogenic and/or anionic surfactants and mixtures of surfactants with high emulsifying, dispersing and wetting properties. Examples suitable for this purpose anionic, nonionic and cationogenic surfactants are described in particular in WO 97/34485 on p.7 and 8. In addition, to obtain the proposed invention herbicide compositions suitable also commonly used in cooking techniques preparative forms of surfactants, which are described in particular in "McCutcheon''s Detergents and Emulsifiers Annual", published by MC Publishing Corp., Ridgewood New Jersey, 1981, Stache, H., "Tensid-Taschenbuch", publishing house Carl Hanser Verlag, Munchen/Wien, Vienna, 1981 and M. and J. Ash, "Encyclopedia of Surfactants", so I-III, published by Chemical Publishing Co., New York, 1980-81.

Herbicide compositions usually contain from 0.1 to 99 wt.%, especially from 0.1 to 95 wt.%, the active ingredients in the form of a mixture of compounds of formula I, compounds among the compounds of formulae 2.1 to 2.51 and compounds of formulae 3.1 to 3.16, from 1 to 99.9 wt.% solid or liquid auxiliary substances is STV, used in the preparative form, and from 0 to 25 wt.%, first of all, from 0.1 to 25 wt.%, Surfactants. If included in sale products preferred compositions in the form of concentrates, the end user usually uses diluted preparations.

Such compositions may also contain other additives, such as stabilisers, for example vegetable oils or epoxydecane vegetable oil (epoxydecane coconut oil, rapeseed oil or soybean oil), antispyware, for example silicone oil, preservatives, viscosity regulators, binders, adhesives, as well as fertilizers or other active ingredients. To apply the antidotes of formulae 3.1 to 3.16 or compositions containing them in order to protect cultivated plants from the adverse effects of herbicides of formula I and 2.1-2.51 various suitable methods and technologies, for example, described below.

I) seed Dressing

a) seed Treatment, make use of a prepared in the form of a wettable powder of the compounds of formulae 3.1 to 3.16 by shaking in an appropriate vessel until uniform distribution of the drug on the surface of the seeds (dry etching). Use about 1 to 500 g of compound of formulae 3.1 to 3.16 (4 g to 2 kg of wettable powder) per 100 kg of seed.

b) Etching the seed emulgirujushchie concentrate compounds of formulae 3.1 to 3.16 carried out according to the above described method a) (wet dressing).

b) seed Treatment is conducted by immersing for 1-72 hours in the working solution containing from 100 to 1000 ppm million compounds of formulae 3.1 to 3.16, and then the seeds if necessary, dried (wet etching by immersion).

Seed treatment or processing of germinated seeds are probably the preferred methods of processing, because such a treatment, the active ingredients are fully interacts with the target culture. The consumption rate of the antidote is usually from 1 to 1000 g, preferably from 5 to 250 g per 100 kg of seed material with the rate depending on the technique, allowing the addition of other active ingredients or micronutrients may differ from these limits both in big, and the smaller side (repeat dressing).

II) a Treatment tank mixtures

In this case, use is brought to a liquid state, the mixture of antidote and herbicide (mutual quantitative ratio of the components is from 10:1 to 1:100), and the rate of application of herbicide is 0.005 to 5.0 kg per hectare. Processing such bukovymi mixtures is carried out before or after sowing.

III) Introducing into the seed furrow

Compounds of formulae 3.1 to 3.16 in the form mulgirigala concentrate, wettable powder or granules contribute openly planted semen the Yu furrow. After closing the seed furrow in the usual way spend redshadow processing herbicide.

IV) Controlled release of the active substance

Compounds of formulae 3.1 to 3.16 applied from a solution in mineral granular media or polymer granules (urea/formaldehyde) and dried. Then if necessary, you can apply an extra coating the granulate in the shell), which allows for a certain amount of time to visvabharati active ingredient in dosed quantities.

Below are the compounds most preferred compositions according to the invention (% = wt.%).

Mulgirigala concentrates:
the mixture of active ingredients:1-90%, preferably 5-20%
surfactant:1-30%, preferably 10-20%
carrier liquid:5-94%, preferably 70-85%
Dusty:
the mixture of active ingredients:0.1 to 10%, preferably 0.1 to 5%
carrier liquid:of 99.9 to 90%, preferably about 99.9 to 99%
Suspension concentrates:
the mixture of active ingredients:5-75%, predpochtitel is about 10-50%
water:94-24%, preferably 88-30%
surfactant:1-40%, preferably 2-30%
Wettable powders:
the mixture of active ingredients:0.5 to 90%, preferably 1-80%
surfactant:0.5 to 20%, preferably 1-15%
solid carrier:5-95%, preferably 15-90%
Granules:
the mixture of active ingredients:0.1 to 30%, preferably 0.1 to 15%

solid carrier:of 99.5 to 70%, preferably 97-85%

Below the invention is illustrated in the examples, not limiting its scope.

Examples of compositions in the form of mixtures of herbicides of formula I, optionally herbicides of the formulae 2.1 to 2.51 and antidotes of formulae 3.1 to 3.16 (%= wt.%).

F1. Mulgirigala concentratesa)b)in)g)
the mixture of active ingredients5%10%25%50%
dodecylbenzenesulfonate calcium6%8%6% 8%
polyglycidyl ether of castor oil (36 moles of ethylene oxide)4%-4%4%
polyglycolic ether op (7-8 moles of ethylene oxide)-4%-2%
cyclohexanone--10%20%
the mixture arene. hydrocarbon, C9-C1285%78%55%16%
Such concentrates can be obtained emulsions of any desired concentration by dilution with water.
F2. Solutionsa)b)in)g)
the mixture of active ingredients5%10%50%90%
1-methoxy-3-(3-methoxypropane)propane-20%20%-
polyethylene glycol 400 MM20%10%--
N-methyl-2-pyrrolidone--30%10%
the mixture arene. hydrocarbon, C9-C1275%60%--
what these solutions are suitable for use in the form of microdrops.
F3. Wettable powdersa)b)in)g)
the mixture of active ingredients5%25%50%80%
sodium lignosulphonate4%-3%-
sodium lauryl sulfate2%3%-4%
diisobutyldimethoxysilane sodium-6%5%6%
polyglycolic ether op (7-8 moles of ethylene oxide)-1%2%-
highly dispersed silicic acid1%3%5%10%
kaolin88%62%35%-

The active ingredient is mixed to homogeneity with auxiliary substances and the resulting mixture is thoroughly ground in a suitable for this purpose mill, receiving wettable powders which can be diluted with water to obtain suspensions of any desired concentration.

F4. Granules coateda)b)in)Ȋ
the mixture of active ingredients0,1%5%15%
highly dispersed silicic acid0,9%2%2%
inorganic media (⊘ 0,1-1 mm), for example, caso3or SiO299,0%93%83%
The active ingredient is dissolved in methylene chloride and spray applied to the carrier, after which the solvent is evaporated in vacuum.
F5. Granules coateda)b)in)
the mixture of active ingredients0,1%5%15%
polyethylene glycol 200 MM1,0%2%3%
highly dispersed silicic acid0,9%1%2%
inorganic media (⊘ 0,1-1 mm), for example, caso3or SiO298,0%92%80%
The finely ground active ingredient is uniformly applied, in a mixer on medium wetted polietilene the MCPFE. In this way receive a dust free granules coated.
F6. Extruded granulesa)b)in)g)
the mixture of active ingredients0,1%3%5%15%
sodium lignosulphonate1,5%2%3%4%
carboxymethylcellulose1,4%2%2%2%
kaolin97,0%93%90%79%
The active ingredient is mixed and milled with auxiliary substances and the resulting mixture is moistened with water. Then this mixture ekstragiruyut and then dried in the air stream.
F7. Dustya)b)in)
the mixture of active ingredients0,1%1%5%
talc39,9%49%35%
kaolin60,0%50%60%

Ready-to-use dusty obtained by mixing the active ingredient with the carriers and grinding the mixture in rhodney for this purpose the mill.

F8. Suspension concentratesa)b)in)g)
the mixture of active ingredients3%10%25%50%
ethylene glycol5%5%5%5%
polyglycidyl ether of Nonylphenol (15 moles of ethylene oxide)-1%2%-
sodium lignosulphonate3%3%4%5%
carboxymethylcellulose1%1%1%1%
37%aqueous formaldehyde solution0,2%0,2%0,2%0,2%
silicone oil emulsion0,8%0,8%0,8%0,8%
water87%79%62%38%

The finely ground active ingredient is mixed to homogeneity with auxiliary substances, receiving a suspension concentrate from which the dilution water can be obtained suspensions of any desired concentration.

In practice it is often more expedient separately on the tee to prepare the compositions based on the compounds of formula I, 2.1-2.51 and 3.1-3.16, and then shortly before use to combine these compounds in water in the respective treatment device in the desired proportions to obtain the so-called "tank mixtures".

The ability of the antidotes of formulae 3.1 to 3.16 to protect cultivated plants from phyto-toxic action of herbicides of formula I is illustrated in the following examples.

Biological example: Protective effect as antidote

Pilot plants are grown in plastic pots under greenhouse conditions until stage 4 leaves. At this stage of the experimental plants treated only with herbicides, as well as mixtures of herbicides with the tested compounds investigated for their effect as antidotes. The treatment is carried out with an aqueous suspension of the test compounds, obtained from a 25%wettable powder (example F3, b)), with a flow rate of 500 l of water/ha 4 weeks after treatment as a percentage appreciate phyto-toxic effect of herbicides on crop plants, such as corn and grains. 100% corresponds to the total loss experienced by plants and 0% corresponds to the total absence of phyto-toxic action.

Obtained in this experiment the results indicate that the use of compounds of formulae 3.1 to 3.16 can significantly reduce damage to cultivated plants with the herbicide of formula I, and is used in combination with one or more herbicides from among the compounds of formulae 2.1 to 2.51. The following table in40 as an example, presents some of the data obtained in this experiment the results on the study of the protective action of the antidote.

Table in40
Experienced plantConn. 1.001 [50 g/ha]Conn. 1.001 [50 g/ha] + Conn. 3.3 [50 g/ha]Conn. 1.001 [50 g/ha] + Conn. 3.1 [50 g/ha]Conn. 1.001 [50 g/ha] + Conn. 3.8 [50 g/ha]
Corn50550
Abutilon100100100100
Setaria100100100100

The same results were obtained with the application of the compounds specified in the examples F1, F2 and F4-F8 formulations.

Biologically examples.

A synergistic effect was observed in the case when the action of the combination of active ingredients, i.e. compounds of the formula I and 2.1-2.51, exceeds the total effect can be achieved with the use of each of the active ingredients separately.

Test the connection:

As the compounds of formula I take connection # 1.037

As the compounds of formulae 2.1 to 2.51 take the compound of formula 2.9

in which R69means the nitrogroup.

Expected herbicide action We for a given combination of two herbicides can be calculated by the formula below Colby (see S.R. COLBY, "Calculating synergistic and antagonistic response of herbicide combinations". Weeds 15, p.20-22, 1967):

We=X+[Y•(100-X)/100],

where X is expressed as the percentage of herbicide action when processing a compound of formula I with a consumption rate of p kg / ha compared to the untreated control (=0%),

Y is expressed as the percentage of herbicide action when processing a compound of formula 2.9, in which R69means NO2when the rate of flow q kg per hectare compared to the untreated control,

We expected herbicide action (herbicide action in percentage of untreated control) as a result of processing a compound of formula 2.9, in which R69means NO2when the rate of application of p+q kg of active ingredient per hectare.

When in fact the observed action exceeds the expected value We place a synergistic effect.

The presence of a synergistic effect when using the compounds of formula I in combination with the compound of the formula 2.9, in which R69means NO2, the following examples.

Description of experiment: preschedule action

One - and two pilot plants are sown in plastic pots with the norm of the th greenhouse-greenhouse soil mixtures. Immediately after sowing by spraying spend processing the test compounds in the form of an aqueous suspension (500 litres of water/ha). Consumption rates depend on the optimal dose determined separately for field and greenhouse conditions. After this pilot plants grown in the greenhouse under optimal conditions. Effect of herbicides on the experimental plants are estimated through 30 days (in %, 100% corresponds to complete loss of plants, 0% corresponds to no phyto-toxic action). Examples confirming the existence of a synergistic effect in the application proposed in the invention compositions are presented in table B41 content:

Table B41 content:

preschedule action
Experienced plantConn. 1.037 [100 g/ha]Conn. 2.9 [100 g/ha]Conn. 1.037 [100 g/ha] + Conn. 2.9 [100 g/ha]We according to Colby
Polygonum5007050
Experienced plantConn. 1.037 [100 g/ha]Seed [50 g/ha]Conn. 1.037 [50g/ha] + Conn. 2.9 [50 g/ha]We according to Colby
Setaria F.8009080

Description of experiment: polished is the first action

Pilot plants are grown in plastic pots under greenhouse conditions to the stage of 2-3 leaves under greenhouse conditions. For cultivation as a substrate using normative greenhouse-greenhouse soil mixtures. At the stage of 2-3 leaves of the experimental plants treated with herbicide individually and as a mixture. The processing using aqueous suspension of the test compounds in 500 l of water/ha consumption rates depend on the optimal dose determined separately for field and greenhouse conditions. Effect of herbicides on the experimental plants are estimated through 30 days (in %, 100% corresponds to complete loss of plants, 0% corresponds to no phyto-toxic action). Examples confirming the existence of a synergistic effect in the application proposed in the invention compositions are presented in table V:

Table V:

post-harvest action
Experienced plantConn. 1.037 [50 g/ha]Seed [50 g/ha]Conn. 1.03 7 [50 g/ha] + Conn. 2.9 [50 g/ha]We according to Colby
Geranium4006040
Setaria V.70208070
Experienced plant Seed [50 g/ha]Conn. 2.9 [25 g/ha]Conn. 1.037 [50 g/ha] + Conn. 2.9 [25 g/ha]We according to Colby
Polygonum306010072

1. Composition selective herbicide action, which in addition is usually used in cooking techniques preparative forms inert excipients contains as active ingredient a mixture of

a) herbicide effective amount of the compounds of formula I

in which R in each case independently mean C1-C6alkyl, C1-C6haloalkyl,1-C4alkoxy-C1-C4alkyl or C1-C4alkoxy-C1-C4alkoxy-C1-C4alkyl;

m means 2;

Q means a group of Q2

in which R23means a hydroxy-group and

Y means With1-C4Allenby bridge;

or agronomically acceptable salt of such a compound, and b) a synergistically effective amount of one or more compounds selected from the group comprising a compound of formula 2.1

in which R51means of CH2-OMe and the and ethyl, R52means hydrogen;

the compound of formula 2.2

in which R53means ethyl, R54means methyl or ethyl, a R55means-CH(Me)-CH2OMe, CH2OMe or CH2O-CH2CH3;

the compound of formula 2.3

in which R56means CH(Me)-CH2OMe;

the compound of formula 2.4

in which R57means chlorine or metalcorp, R58means ethyl, and R59means ethyl, isopropyl or tert-butyl;

the compound of formula 2.6

in which R62means hydrogen, R63means methyl, R64means fluorine, R65means hydrogen, Y represents nitrogen, Z means Metin, and R66means fluorine;

the compound of formula 2.7

in which R67means-C(O)-S-n-octyl;

the compound of formula 2.9

in which R69means nitrogroup;

the compound of formula 2.12

in which R73mean NH2;

the compound of formula 2.13

1means Metin, Y2means Metin, Y3means Metin, Y4means Metin, Y5mean nitrogen or Metin, Y6means methyl, dipterocarp or trifluoromethyl, Y7means a methoxy group or dipterocarp and R74means the Sooma or CH2-CH2CF3or its sodium salt,

the compound of formula s

the compound of formula 2.14

the compound of formula 2.16

the compound of formula 2.18

the compound of formula 2.19

the compound of formula 2.21

the compound of formula 2.25

the compound of formula 2.30

the compound of formula 2.33

2. A way of combating the growth of unwanted plants in crops of useful plants, namely, that a cultivated plant or place of its growth process herbicide-effective amount of a composition according to claim 1.

3. Composition selective herbicide action, which along with the usual netname auxiliary substances, used in cooking techniques preparative forms, such as carriers, solvents and wetting agents, as the active ingredient is a mixture of

a) herbicide-synergistic effective amount of 4-hydroxy-3-(2-methyl-6-triptorelin-3-carbonyl)bicyclo[3.2.1] Oct-3-EN-2-she according to claim 1 and the compounds of formula 2.2 according to claim 1, and

b) herbicide-antagonistically effective amount of the compounds of formula 3.1

4. Composition selective herbicide action, which along with the usual inert excipients used in the preparation technology preparative forms, such as carriers, solvents and wetting agents, as the active ingredient is a mixture of

a) herbicide effective amount of 4-hydroxy-3-(2-methyl-6-triptorelin-3-carbonyl)bicyclo[3.2.1]Oct-3-EN-2-she according to claim 1, and

b) herbicide-antagonistically effective amount of a compound selected from the group comprising the compound of formula 3.1

the compound of formula 3.3

the compound of formula 3.8

5. Process for the selective combating of weeds and grasses in crops of useful the x plants it lies in the fact that the useful plants, seeds or cuttings or area of their cultivation process herbicide-effective amount of a composition according to claim 4.

The priority of claims 1 to 5, where the herbicide agent contains a compound of the formula (I)in which R represents a C1-C6-alkyl or C1-C6-haloalkyl - 25.01.2000.

The priority of claims 1 to 5, where the herbicide agent contains a compound of the formula (I)in which R represents a C1-C4-alkoxy-C1-C4alkyl or C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl - 09.06.2000.



 

Same patents:

FIELD: agrochemistry.

SUBSTANCE: invention provides a stable aqueous formulation of hydrophobic pesticide by emulsifying aqueous phase and a water-immiscible phase, the former containing poly(alkylene glycol) ether and the latter hydrophobic pesticide and one or several emulsifiers selected from group including carboxylate, sulfate, sulfonate, alcohol solutions of ethoxylated and alkylphenolethoxylate, fatty acid ethyl ester, sorbitol ester, ethoxylated fat or oil, aminoethoxylate, ethylene oxide/propylene oxide copolymer, fluorocarbon, and siliceous polymer.

EFFECT: increased stability of formulations.

38 cl, 1 tbl, 12 ex

FIELD: agriculture, in particular herbicide compositions.

SUBSTANCE: invention relates to weed controlling method for tolerant cotton crops using (A) road spectrum herbicides selected from group (A1) glufosinate (salt) and related compounds; (A2) glyphosate (salt) and related compounds; and (B) herbicides selected from group containing diurone, trifluraeline, linuron, and pendimethalin; lactofen, oxyfluoren, bispiribac and salts thereof, pyrithiobac and salts thereof; setoxydim, cyclosidim, and cletodim; wherein components (A) and (B) are used in synergistically effective ratio. Also are described herbicide compositions containing compound from group (A1) or (A2) and herbicide from group (B).

EFFECT: effective controlling of weeds in cotton crops.

9 cl, 12 tbl, 3 ex

FIELD: agriculture, in particular method for controlling of weeds.

SUBSTANCE: claimed method for controlling of weeds in tolerant maize cultures includes application of composition comprising (A) road spectrum herbicide from group (A1) glufosinate (salt) and analogs, (A2) glyfosate (salt) and analogs; (B) one or more herbicides from group (B1) cyanazin, alachlor, nicosulfurone, rimsulfurone, sulkotrion, mesotrion, and penthoxamid; (B2) pendimethalyne, methosulam, isoxaflutol, metribuzin, chloransulam, flumetsulam, linuron, florasulam, and isoxachlorotol; and (B3) bromoxinyl, chlorpyralid, tifensulfuron, MCPA (2-methyl-4-chlorophenoxyacetic acid), halosulfuron, and sulfosulfuron, wherein (A) and (B) components are in synergic effective ration. Also disclosed are herbicidal compositions including compound from group (A1) or )F2) and herbicide from group (B).

EFFECT: effective controlling of weeds in tolerant maize cultures.

6 cl, 55 tbl, 3 ex

FIELD: agriculture, in particular herbicide compositions.

SUBSTANCE: invention relates to weed controlling method for tolerant grain crops using (A) road spectrum herbicides selected from group (A1) glufosinate (salt) and related compounds; (A2) glyphosate (salt) and related compounds; and (B) one or more herbicides selected from group containing (B1) herbicides selectively effecting in grain crops especially against monocotyledonous weeds effecting on folia and/or soil (residual benefit); or (B2) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting especially on folia; or (B3) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting on folia or soil; or (B4) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting on folia; wherein components (A) and (B) are used in synergic ration. Also are described herbicide compositions containing (A1) ) glufosinate (salt) and related compounds and herbicide from group (B); as well as herbicide compositions containing(A2) glyphosate (salt) and related compounds and herbicide from group (B); wherein components (A) and (B) are used in synergically effective ration.

EFFECT: effective controlling of weeds in grain crops.

6 cl, 70 tbl, 3 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes a synergistic composition of herbicides comprising components (A) and (B) wherein (A) represents herbicide taken among the group of the formula (I):

wherein R1 means (C1-C4)-alkyl; R2 means (C1-C4)-alkyl; R3 means hydrogen atom; X and Y mean (C1-C4)-alkoxy-group; (B) represents one or two herbicides taken among the group of compounds or their acceptable forms: alachlor, metolachlor, acetochlor, dimetenamide, atrazine, cyanasin, metribusin, fluthiamide, nicosulfuron, rimsulfuron, primisulfuron, pendimetalin, sulcotrion, dicamba, mesotrion, isoxachlortol, metosulam, anilofos, fenoxaprop-ethyl, setoxydim, diclofop-methyl, MCPA, bromoxynil, pyridat, clopyralid, iodosulfuron-methyl, ethoxysulfuron, amidosulfuron, gluphosinat-amminium, isopropylammonium-glyphosate, imasetapir wherein components (A) and (B) are taken in the effective doses. Also, invention describes a method for control of weeds by using above indicated herbicide composition. Invention provides the development of the synergistic herbicide composition eliciting high activity.

EFFECT: improved method for control, valuable properties of composition.

6 cl, 26 tbl, 3 ex

The invention relates to the field of plant protection products that can be used against weeds in tolerant or resistant crops sugar beet and which as a herbicide biologically active substances contain a combination of two or more herbicides

The invention relates to systems of surfactants for liquid water or water-organic compositions containing mainly organic and aqueous phase in the form of a microemulsion

The invention relates to chemical herbicides used for the destruction of unwanted vegetation

FIELD: agriculture, in particular chemical agents for plant protection.

SUBSTANCE: sulfonylaminourea and phenoxyacetic acid derivatives-based herbicidal composition contains nonionic surfactant, anion-active surfactant sulfonol, kaolin as carrier, and carbon white. As sulfonylaminourea and phenoxyacetic acid derivatives it contains 3-(6-methyl-4-methoxy-1,3,5-triazinyl-2-)-1-(2-chlorophenylsulphonyl)urea and 2-methyl-4-chlorophenoxyacetic acid sodium salt, respectively. Additionally composition contains triethanolamine or diethanolamine, disubstituted potassium phosphate as stabilizer in the component ratio of (mass %): 2-methyl-4-chlorophenoxyacetic acid sodium salt 55-72; 3-(6-methyl-4-methoxy-1,3,5-triazinyl-2-)-1-(2-chlorophenylsulphonyl)urea 0.3-0.4; nonionnic surfactant 0.05-0.15; sulfonol 0.05-0.15; triethanolamine or diethanolamine 0.15-0.2; carbon white 0.37-1.5; disubstituted potassium phosphate 1.0-2.0; and balance: kaolin. Composition components are separately applied on carrier surface. More specifically triethanolamine or diethanolamine is separately mixed with kaolin; 3-(6-methyl-4-methoxy-1,3,5-triazinyl-2-)-1-(2-chlorophenylsulphonyl)urea, and carbon white are separately mixed with kaolin; disubstituted potassium phosphate, nonionic surfactant, and sulfonol are separately mixed with kaolin; and 2-methyl-4-chlorophenoxyacetic acid sodium salt also is separately mixed with kaolin. Mixtures are conditioned for 24 h at room temperature and then are blended to provide mentioned above component ratio in product.

EFFECT: herbicidal composition of increased activity and deferred hydrolysis in wetted powder.

3 cl, 6 ex, 2 tbl

FIELD: agriculture, herbicides.

SUBSTANCE: invention relates to herbicide composition based on derivative of sulfonylurea that comprises non-ionogenic surface-active substance, lignosulfonates as anion-active surface-active substance and highly dispersed amorphous silica as a carrier. Composition comprises chlorsulfuron as derivative of sulfonylurea and triethanolamine or diethanolamine additionally, and potassium dihydrogen phosphate as a stabilizing agent in the following ratio of components, wt.-%: chlorsulfuron, 18-22; non-ionogenic surface-active substance, 3-5; potassium dihydrogen phosphate, 9-12; triethanolamine or diethanolamine, 9-11; lignosulfonates, 3-10, and highly dispersed amorphous silica, the balance. Method involves mixing components in indicated ratios by steps for 3 stages. At the 1-st stage triethanolamine or diethanolamine is applied on surface of highly dispersed amorphous silica, at the 2-d stage - chlorsulfuron, and at 3-d stage - potassium dihydrogen phosphate, lignosulfonates and non-ionogenic surface-active substance. After keeping for 24 h at the room temperature mixing products from all three stages are combined. Invention provides enhancing stability of chlorsulfuron and biological activity of preparation based on thereof. Invention is designated for applying in agriculture.

EFFECT: valuable properties of herbicide composition.

4 cl, 2 tbl, 9 ex

FIELD: agriculture, in particular herbicide compositions.

SUBSTANCE: invention relates to weed controlling method for tolerant cotton crops using (A) road spectrum herbicides selected from group (A1) glufosinate (salt) and related compounds; (A2) glyphosate (salt) and related compounds; and (B) herbicides selected from group containing diurone, trifluraeline, linuron, and pendimethalin; lactofen, oxyfluoren, bispiribac and salts thereof, pyrithiobac and salts thereof; setoxydim, cyclosidim, and cletodim; wherein components (A) and (B) are used in synergistically effective ratio. Also are described herbicide compositions containing compound from group (A1) or (A2) and herbicide from group (B).

EFFECT: effective controlling of weeds in cotton crops.

9 cl, 12 tbl, 3 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to new substituted thienyl(amino)sulfonylureas of formula I ,

wherein A represents nitrogen or methane; Q represents direct bond or imino; R1 represents fluorine, chlorine, bromine, unsubstituted C1-C4-alkyl, C1-C4-alkoxyl optionally substituted with halogen, unsubstituted C1-C4-alkylthio, or di(C1-C4-alkyl)amino; R2 represents hydrogen or C1-C4-alkyl. Compounds of present invention are useful as herbicide agents.

EFFECT: new compounds with herbicide activity.

5 cl, 11 tbl, 5 ex

FIELD: agriculture, in particular method for controlling of weeds.

SUBSTANCE: claimed method for controlling of weeds in tolerant maize cultures includes application of composition comprising (A) road spectrum herbicide from group (A1) glufosinate (salt) and analogs, (A2) glyfosate (salt) and analogs; (B) one or more herbicides from group (B1) cyanazin, alachlor, nicosulfurone, rimsulfurone, sulkotrion, mesotrion, and penthoxamid; (B2) pendimethalyne, methosulam, isoxaflutol, metribuzin, chloransulam, flumetsulam, linuron, florasulam, and isoxachlorotol; and (B3) bromoxinyl, chlorpyralid, tifensulfuron, MCPA (2-methyl-4-chlorophenoxyacetic acid), halosulfuron, and sulfosulfuron, wherein (A) and (B) components are in synergic effective ration. Also disclosed are herbicidal compositions including compound from group (A1) or )F2) and herbicide from group (B).

EFFECT: effective controlling of weeds in tolerant maize cultures.

6 cl, 55 tbl, 3 ex

FIELD: organic chemistry, agriculture, herbicide composition.

SUBSTANCE: invention relates to herbicide composition, containing conventional inert additives and mixture of a) herbicidically effective amount of substance satisfying the formula I [in formula R1 and R3 are the same or different C1-C4-alkyl; R4 and R5 together form groups of formulae: -C-R6(R7)-O-C-R8(R9)-C-R10(R11)-C-R12(R13)-(Z1), -C-R14(R15)-C-R16(R17)-O-C-R18(R19)-C-R20(R21)-(Z2), or -C-R22(R23)-C-R24(R25)-C-R26(R27)-O-C-R28(R29)-(Z3), wherein each R6-R29 is hydrogen; G is hydrogen or -C(X2)-X3-R31; X2 and X3 independently are oxygen; R31 is C1-C10-alkyl]; b) herbicidic synergic amount of at least one herbicide selected from group containing sulfonylureas, phenoxyacetic acids, as well as florsulam, tralcoxidim, klodinafol-propargil, phenoxaprop-P-ethyl, trifluramine, pendimethaline, picolinafen, etc. Composition also may contain safety effective amount of protective agent, such as chloquintocet-mexyl and additive (e.g., mineral oil or C8-C22-fat acid alkyl esters) in amount of 0-2 mass %. Also disclosed is method for selective controlling of weeds and grassy plants in cultural plants by treatment of cultural plants, seeds or seedlings thereof, or vegetation area thereof with claimed composition.

EFFECT: effective composition and method for weed controlling.

5 cl, 11 tbl, 7 ex

FIELD: agriculture, in particular herbicide compositions.

SUBSTANCE: invention relates to weed controlling method for tolerant grain crops using (A) road spectrum herbicides selected from group (A1) glufosinate (salt) and related compounds; (A2) glyphosate (salt) and related compounds; and (B) one or more herbicides selected from group containing (B1) herbicides selectively effecting in grain crops especially against monocotyledonous weeds effecting on folia and/or soil (residual benefit); or (B2) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting especially on folia; or (B3) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting on folia or soil; or (B4) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting on folia; wherein components (A) and (B) are used in synergic ration. Also are described herbicide compositions containing (A1) ) glufosinate (salt) and related compounds and herbicide from group (B); as well as herbicide compositions containing(A2) glyphosate (salt) and related compounds and herbicide from group (B); wherein components (A) and (B) are used in synergically effective ration.

EFFECT: effective controlling of weeds in grain crops.

6 cl, 70 tbl, 3 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: claimed mixture from herbicides and antidotes contains (A) herbicidically active substance based on phenylsulfonylureas of formula I and salts thereof (in formula R1 is hydrogen or C1-C6-alkyl; R2 is C1-C3-alkyl; R3 is C1-C3-alkoxy; R4 is hydrogen or C1-C4-alkyl; Hal is fluorine, chlorine, bromine, or iodine); and (B) antidote of formulae II or III , wherein X is hydrogen, halogen, C1-C4-alkyl; C1-C4-alkoxy, nitro or C1-C4-haloalkyl; Z is hydroxyl, C1-C8-alkoxy, C3-C6-cycloalkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy; R5 is C1-C2-alkandiyl chain optionally substituted with one or two C1-C4 alkyl residues or (C1-C3-alcoxy)carbonyl; W is bivalent heterocyclic residue; n = 1-5; in weight ratio herbicide/antidote of 100:1-1:100. Also disclosed is method for protection of cultural plants against phytotoxic side effect of herbicidically active substance of formula I. Claimed method includes antidote application of formulae II or III on plant, plant parts, plant seeds or seeding areas before or together with herbicidically active substance in amount of 0.005-0.5 kg/hectare in weight ratio of 100:1-1:100.

EFFECT: mixture for effective selective weed controlling in cultural plant, particularly in maize and grain cultures.

8 cl, 2 ex, 7 tbl

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes a synergistic composition of herbicides comprising components (A) and (B) wherein (A) represents herbicide taken among the group of the formula (I):

wherein R1 means (C1-C4)-alkyl; R2 means (C1-C4)-alkyl; R3 means hydrogen atom; X and Y mean (C1-C4)-alkoxy-group; (B) represents one or two herbicides taken among the group of compounds or their acceptable forms: alachlor, metolachlor, acetochlor, dimetenamide, atrazine, cyanasin, metribusin, fluthiamide, nicosulfuron, rimsulfuron, primisulfuron, pendimetalin, sulcotrion, dicamba, mesotrion, isoxachlortol, metosulam, anilofos, fenoxaprop-ethyl, setoxydim, diclofop-methyl, MCPA, bromoxynil, pyridat, clopyralid, iodosulfuron-methyl, ethoxysulfuron, amidosulfuron, gluphosinat-amminium, isopropylammonium-glyphosate, imasetapir wherein components (A) and (B) are taken in the effective doses. Also, invention describes a method for control of weeds by using above indicated herbicide composition. Invention provides the development of the synergistic herbicide composition eliciting high activity.

EFFECT: improved method for control, valuable properties of composition.

6 cl, 26 tbl, 3 ex

The invention relates to the field of plant protection products that can be used against weeds in tolerant or resistant crops sugar beet and which as a herbicide biologically active substances contain a combination of two or more herbicides

FIELD: organic chemistry, veterinary science.

SUBSTANCE: invention relates to a method for control over exto- and endoparasites taken among group including acariform mites, parasitoformous mites and nematodes parasitizing in animals, productive cattle and domestic animals. Method involves applying veterinary preparation comprising 1-[4-chloro-3-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluoro)urea and compound of the formula (i):

wherein R1 means one of radicals:

or ; R2 means -CH(CH3)-CH3, -CH(CH3)-C2H5, -C(CH3)=CH-CH(CH3)2 or cyclohexyl; R3 means hydrogen atom or hydroxy-group if a bond between atoms 22 and 23 represents a double bond, or it means hydrogen atom or group =N-O-CH3 if an ordinary bond presents between atoms 22 and 23; R4 means HO-, and the preparation can be in free form or in physiologically acceptable form. Invention provides preparing preparations with good tolerance and rapid effect and persistence with respect to different helminth-associated diseases, parasitiformous and acariformous mites being without adverse effect on normal behavior of animals.

EFFECT: valuable properties of compounds.

7 cl, 3 tbl, 8 ex

Up!