Herbicide composition, method for selective controlling of weeds and grassy plants

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

 

The present invention relates to new synergistic herbicide compositions selective action to combat herbaceous plants and weeds in crops of cultivated plants, in particular in crops of corn and grain crops, these compositions contain the herbicide 3-hydroxy-4-(4-were)-5-oxadiazolyl synergistic activity amount of at least one of the second herbicide, and optional oil additive and/or the security agent (the antidote), as well as to the use of these compositions for controlling weeds in crops of cultivated plants.

When applying herbicides cultivated plants can also suffer serious damage depending on, for example, on factors such as the concentration of the herbicide and method of making the features of the agricultural plants, the soil and climatic conditions, such as characteristics of light, temperature and rainfall. To solve this and similar problems have already been proposed to use various compounds as antidotes to counteract the harmful effects of the herbicide on the cultivated plant, i.e. to protect him from a cultivated plant, while maintaining almost without reducing herbicide effects on weeds must be destroyed.

However, it was found that p is izlojennye the antidotes often have a very specific effect not only in terms of cultivated plants, but in relation to herbicide, which in some cases also depends on the method of application, i.e. a specific antidote can often be only suitable for concrete plants and concrete class of herbicides or specific herbicide. For example, it was found that the antidotes logintest and logintest-mexyl and mefenpyr and mefenpyr-diethyl described in EP-A-0191736 (connection 1.316) and in WO 91/07874 (example 3), and is described in The Pesticide Manual, 11th ed., British Crop Protection Council, Entry No. 154 and 462, have the ability to protect cultivated plants from phyto-toxic effects of certain 3-hydroxy-(4-were)-5-oxadiazoline derivatives, but in some cases they reduce herbicide activity against weeds.

In US-A-4834908 described some combination of oil additives that increase herbicide action of compounds from the class of cyclohexandione, benzothiadiazines, herbicides, which are diphenyl ethers, and herbicides, which are aryloxypropanolamine.

Although 3-hydroxy-(4-were)-5-oxadiazoline derivatives according to the structure quite different from the compounds described in US-A-4834980, the combination of these oil additives with the specified 3-hydroxy-(4-were)-5-oxadiazoline derivatives also leads to an increase herbicide activity, but this is m a cultivated plant also heavily damaged. Thus, the mixture of the herbicide/oil additives cannot be used for selective weed control in crops of cultivated plants.

With the invention it has been unexpectedly found that weeds can be very successfully selectively to fight when using certain 3-hydroxy-(4-were)-5-oxopentanoic herbicides without damaging the crop plants, by making these compounds in combination with synergistic activity of a quantity of at least one of the second herbicide, and optionally also in combination with the additive, including vegetable oil or animal or mineral oil, their complex alkalemia esters or blends of these oils and oil derivatives, and the antidotes logintime or mefenpyr.

Thus, the invention relates to herbicide compositions of selective action, containing, along with the usual formulation of inert additives, such as carriers, solvents and wetting agents, as deistvuyushego substance mixture including

a) herbicide effective amount of the compounds of formula I

where

R1and R3each independently of one another denotes halogen, nitro, cyano, C1-C4alkyl, C2-C4alkenyl,2-C4 quinil,1-C4haloalkyl,2-C6haloalkyl,3-C6cycloalkyl, galatarasay3-C6cycloalkyl,2-C6alkoxyalkyl,2-C6alkylthiomethyl, hydroxy, mercapto, C1-C6alkoxy, C3-C6alkenylacyl,3-C6alkyloxy, carbonyl, carboxyl,1-C4alkylsulphonyl,1-C4hydroxyalkyl,1-C4alkoxycarbonyl,1-C4alkylthio,1-C4alkylsulfonyl, C1-C4alkylsulfonyl, amino, C1-C4alkylamino or di(C1-C4alkyl)amino;

R4and R5together denote a group

-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)- (Z2or

-C-R22(R23)-C-R24(R25)-C-R26(R27)-O-C-R28(R29)- (Z3),

where R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28and R29each independently of one another denotes hydrogen, halogen, C1-C4alkyl or C1-C4galaal the sludge, and alkylene ring, which together with the carbon atoms of the groups Z1, Z2or Z3contains from 2 to 6 carbon atoms and which may include oxygen, can be either ballirano, or connected through spirostane with the carbon atoms of the groups Z1, Z2or Z3or is it alkylene ring may be connected by a bridge with at least one ring atom of the group Z1, Z2or Z3;

G represents hydrogen,- (X1)-R30With(X2)-X3-R31, -C(X4)-N(R32)-R33, -SO2-R34the cation of an alkali metal, alkaline earth metal, sulfone or ammonium or-P(X5)(R35)-R36or-CH2-X6-R37;

X1, X2, X3, X4X5and X6each independently of one another denotes oxygen or sulfur;

R30, R31, R32and R33each independently of one another denotes hydrogen, C1-C10alkyl, C1-C10haloalkyl, C1-C10cianelli, C1-C10nitroalkyl, C1-C10aminoalkyl,1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl,4-C10alkenylacyl,4-sub> 10alkyloxyalkyl,2-C10alkylthiomethyl,1-C5alkylsulfonyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylidenes-C1-C5alkyl, C1-C5alkylsulphonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminoalkyl-C1-C5alkyl, C1-C5alkylcarboxylic-C1-C5alkyl, C2-C5alkylsulphonyl-(C1-C5alkyl)aminoalkyl,3-C6trialkylsilyl-C1-C5alkyl, panels1-C5alkyl, heteroaryl1-C5alkyl, venoxis1-C5alkyl, heterokaryosis1-C5alkyl, C2-C5alkenyl,2-C5haloalkyl,3-C8cycloalkyl, phenyl or C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines phenyl or heteroaryl or heteroarenes, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines heteroarenes, deteroriating, C1-C3alkyl, C1-C3 haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines deteroriating, phenylamino, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano or nitrosamines phenylamino, diphenylamino, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano or nitrosamines diphenylamino,3-C7cyclooctylamino, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines3-C7cyclooctylamino, dis3-C7cyclooctylamino, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines dis3-C7cyclooctylamino,3-C7cycloalkane or C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines3-C7cycloalkane;

R34, R35and R36denote hydrogen, C1-C10alkyl, C1-C10haloalkyl, C1-C10cianelli, C1-C10nitroalkyl, C1-C10aminoalkyl, 1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl,4-C10alkenylacyl,4-C10alkyloxyalkyl,2-C10alkylthiomethyl,1-C5alkylsulfonyl-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylidenes-C1-C5alkyl, C1-C5alkylsulphonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5alkyl, C2-C8dialkylaminoalkyl-C1-C5alkyl, C1-C5alkylcarboxylic-C1-C5alkyl, C2-C5alkylsulphonyl-(C1-C5alkyl)aminoalkyl,3-C6trialkylsilyl-C1-C5alkyl, panels1-C5alkyl, heteroaryl1-C5alkyl, venoxis1-C5alkyl, heterokaryosis1-C5alkyl, C2-C5alkenyl,2-C5haloalkyl,3-C8cycloalkyl, phenyl or C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines phenyl or heteroaryl heteroarenes, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines heteroarenes, deteroriating, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines deteroriating, phenylamino, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines phenylamino, diphenylamino, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines diphenylamino,3-C7cyclooctylamino, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines3-C7cyclooctylamino, dis3-C7cyclooctylamino, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines dis3-C7cyclooctylamino,3-C7cycloalkane, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines3-the 7cycloalkane, C1-C10alkoxy, C1-C10haloalkoxy,1-C5alkylamino,2-C8dialkylamino and benzyloxy or phenoxy, and benzyl and phenyl groups may themselves be substituted C1-C3the alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano, formyl, acetyl, propionyl, carboxyla,1-C5alkoxycarbonyl, methylthio, ethylthio - or nitro-group;

and R37represents C1-C10alkyl, C1-C10haloalkyl, C1-C10cianelli, C1-C10nitroalkyl, C1-C10aminoalkyl,1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C10alkoxyalkyl,4-C10alkenylacyl,4-C10alkyloxyalkyl,2-C10alkylthiomethyl,1-C5alkylsulfate-C1-C5alkyl, C1-C5alkylsulfonyl-C1-C5alkyl, C2-C8alkylidenes-C1-C5alkyl, C1-C5alkylsulphonyl-C1-C5alkyl, C1-C5alkoxycarbonyl-C1-C5alkyl, C1-C5aminocarbonyl-C1-C5 alkyl, C2-C8dialkylaminoalkyl-C1-C5alkyl, C1-C5alkylcarboxylic-C1-C5alkyl, C2-C5alkylsulphonyl-(C1-C5alkyl)aminoalkyl,3-C6trialkylsilyl-C1-C5alkyl, panels1-C5alkyl, heteroaryl1-C5alkyl, venoxis1-C5alkyl, heterokaryosis1-C5alkyl, C2-C5alkenyl,2-C5haloalkyl,3-C8cycloalkyl, phenyl or C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines phenyl or heteroaryl or heteroarenes, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines heteroarenes, deteroriating, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines deteroriating, phenylamino, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines phenylamine, diphenylamine, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines diphenylamino,3-C7cyclooctylamino, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines3-C7cyclooctylamino, dis3-C7cyclooctylamino, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines dis3-C7cyclooctylamino,3-C7cycloalkane, C1-C3alkyl, C1-C3haloalkyl-, C1-C3alkoxy, C1-C3haloalkoxy-, halo-, cyano - or nitrosamines3-C7cycloalkane or C1-C10alkylsulphonyl; and salts and diastereomers of the compounds I, provided that R1and R3simultaneously denote methyl; and

b) with herbicide synergistic activity amount of at least one herbicide selected from the class phenoxybenzamine acids, hydroxylamines, sulfonylureas, imidazolinones, pyrimidines, triazines, ureas, PPO, chloroacetanilides, PHENOXYACETIC acids, triazines, dinitroanilines, azinones, carbamates, oxoazetidin, thiolcarbamate, salmochelin, benzoic acids, anilides, NITRILES, trions and sulfonamides, and still the herbicides, as amitrol, belforest, bentazon, cinmetacin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, indianian, isoxaben, oxacyclobutane, peridot, perinatal, quinchlorac, quinmerac, tridiphane and planrep; and optional

in) effective to prevent harmful effects of herbicide amount of a safener selected from the group comprising logintest, cation, such as alkali metal, alkaline earth metal, sulfone or ammonium logintime, logintest-mexyl, mefenpyr, cation, such as alkali metal, alkaline earth metal, sulfone or ammonium mefenpyr, and mefenpyr-diethyl; and/or

d) an additive comprising an oil of vegetable or animal origin, or mineral oil, alkalemia esters or blends of these oils and derivatives of oils.

In the context of the present description, the term halogen includes fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. Occurring in the definitions of the substituents of the alkyl group are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl and Pintilie and hexylene isomers. Acceptable cycloalkyl substituents contain from 3 to 6 carbon atoms and represents, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. They can be substituted by one or more atoms ha is ogena, preferably fluorine, chlorine or bromine. Under alkenyl see, for example, vinyl, allyl, methallyl, 1-methylvinyl or but-2-EN-1-yl. Quinil means, for example, ethinyl, propargyl, but-2-in-1-yl, 2-methylbutane-2-yl or but-3-in-2-yl. Haloalkyl groups preferably have a chain comprising 1-4 carbon atoms. Haloalkyl means, 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 or 2,2,2-trichlorethyl, preferably trichloromethyl, diperchlorate, deformity, trifluoromethyl or dichloromethyl. Acceptable haloalkyl radicals include alkeneamine group, substituted by one or more halogen atoms, where the halogen denotes fluorine, chlorine, bromine or iodine and preferably 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. From C2-C6alkenyl groups, substituted 1, 2 or 3 halogen atoms, preferred are groups having a chain consisting of 3-5 carbon atoms. Alkoxygroup preferably have a chain consisting of 1 to 6 carbon atoms. Alkoxygroup means, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butiki, isobutoxy, second-butox is or tert-butoxy or isomers pentyloxy - or hexyloxy, preferably methoxy or ethoxy. Alkylsulphonyl preferably denotes an acetyl or propionyl. Alkoxycarbonyl means, for example, methoxycarbonyl, etoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxide, second-butoxycarbonyl or tert-butoxycarbonyl, preferably methoxycarbonyl or etoxycarbonyl. Ancilliary preferably have a chain comprising 1-4 carbon atoms. Alkylthio means, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutyric, sec-butylthio or tert-butylthio, preferably methylthio or ethylthio. Alkylsulfonyl means, for example, methylsulfinyl, ethylsulfinyl, propylsulfonyl, isopropylphenyl, n-butylsulfonyl, isobutylphenyl, second-butylsulfonyl or tert-butylsulfonyl, preferably methylsulfinyl or ethylsulfinyl. Alkylsulfonyl designates, for example, methylsulphonyl, ethylsulfonyl, propylsulfonyl, isopropylphenyl, n-butylsulfonyl, isobutylphenyl, second-butylsulfonyl or tert-butylsulfonyl, preferably methylsulphonyl or ethylsulfonyl. Alkylamino means, for example, methylamino, ethylamino, n-propylamino, isopropylamino or butylamino isomer. Dialkylamino means, for example, dimethylamino, methylethylamine, diethylamine, n-propylethylene, dibutil the Mino or diisopropylamino, Alkoxyalkyl groups preferably have from 2 to 6 carbon atoms. Alkoxyalkyl means, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxyphenyl or isopropoxide. Alkylthiomethyl means, for example, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiouracil, n-propylthiouracil, isopropylaminomethyl, isopropylaminoethyl, butylthioethyl, butylthioethyl or butylthioethyl. Phenyl may be in substituted form, in each case the substituents can be in the ortho, meta and/or para-position. The preferred positions of the substituents are ortho - and para-position relative to the point of joining the ring.

Heteroaryl groups are aromatic heterocycles, which contain preferably from 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur. Examples of acceptable compounds and heteroaromatic compounds are: pyrrolidine, piperidine, Piran, dioxane, azetidin, oxetan, pyridine, pyrimidine, triazine, thiazole, thiadiazole, imidazole, oxazole, isoxazol and piratin, furan, morpholine, piperazine, pyrazole, benzoxazole, benzothiazole, cinoxacin and quinoline. These heterocyclic compounds and heteroaromatic compounds can be further substituted, for example, halogen, alkyl, alkoxygroup is Oh, haloalkyl, haloalkoxy-, nitro-, cyano, thioalkyl, alkylamino or phenyl. With2-C10alkenyl - and-alkyline group R34may be mono - or polyunsaturated. They contain preferably from 2 to 12 carbon atoms, in particular from 2 to 6 carbon atoms.

The cations of the alkali metal, alkaline earth metal or ammonium, serving as Deputy G, denote, for example, the cations of sodium, potassium, magnesium, calcium and ammonium. Preferred cations of sulfone are, in particular, cations trialkylamine, in which all the alkyl radicals preferably contain from 1 to 4 carbon atoms.

Left-hand free valence of the groups Z1, Z2and Z3linked to position 1, and the right-hand free valence is associated with position 2 pyrazolinones rings.

The compounds of formula I, in which alkylene ring can be bellrowan or connected through spirostane with groups Z1, Z2or Z3from 2 to 6 carbon atoms linked to carbon atoms of the groups Z1, Z2and Z3have, for example, the following structure:

(spirostane) or

(ballirano).

The compounds of formula I, in which alkylene ring in the groups Z1, Z2or Z3 connected by a bridge with at least one ring atom of the group Z1, Z2or z3have, for example, the following structure:

(communication using bridge).

The herbicides of formula I which are preferred for inclusion in compositions according to the invention, R1and R3each independently of one another denotes ethyl, haloacyl, ethinyl,1-C2alkoxy or1-C2haloalkoxy.

Preferred are compositions according to the invention, in which in the formula I R4and R5together denote the group of Z2i.e.-C-R14(R15)-C-R16(R17)-O-C-R18(R19)-C-R20(R21)-where it is most preferable R14, R15, R16, R17, R18, R19, R20and R21denote hydrogen.

In addition, in a preferred group of compositions according to the invention in formula I R30, R31, R32and R33each independently of one another denotes hydrogen, C1-C8alkyl, C1-C8haloalkyl,1-C8cianelli,1-C8nitroalkyl, C1-C8aminoalkyl,2-C5alkenyl,2-C5haloalkyl,3-C8cycloalkyl, C1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C 5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C4alkoxyalkyl,4-C6alkenylacyl,4-C6alkyloxyalkyl,2-C4alkylthiomethyl,1-C4alkylsulfonyl-C1-C2alkyl, C1-C2alkylsulfonyl-C1-C2alkyl, C2-C4alkylidenes-C1-C2alkyl, C1-C5alkylsulphonyl-C1-C2alkyl, C1-C5alkoxycarbonyl-C1-C2alkyl, C1-C5aminocarbonyl-C1-C2alkyl, C2-C8dialkylaminoalkyl-C1-C2alkyl, C1-C5alkylcarboxylic-C1-C2alkyl, C2-C5alkylsulphonyl-(C1-C2alkyl)aminoalkyl,3-C6trialkylsilyl-C1-C5alkyl, panels1-C2alkyl, heteroaryl1-C2alkyl, venoxis1-C2alkyl, heterokaryosis1-C2alkyl, phenyl or heteroaryl;

R34R35and R36each independently of one another denotes hydrogen, C1-C8alkyl, C1-C8haloalkyl,1-C8zenwalker,1-C8nitroalkyl,1-C8aminoalkyl,2-C5alkenyl,2-C5haloalkyl,3-C8cycloalkyl,1-C5Alki the amino-C 1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C4alkoxyalkyl,4-C6alkenylacyl,4-C6alkyloxyalkyl,2-C4alkylthiomethyl,1-C4alkylsulfonyl-C1-C2alkyl, C1-C2alkylsulfonyl-C1-C2alkyl, C2-C4alkylidenes-C1-C2alkyl, C1-C5alkylsulphonyl-C1-C2alkyl, C1-C5alkoxycarbonyl-C1-C2alkyl, C1-C5aminocarbonyl-C1-C2alkyl, C2-C8dialkylaminoalkyl-C1-C2alkyl, C1-C5alkylcarboxylic-C1-C2-alkyl, C2-C5alkylsulphonyl-(C1-C2alkyl)aminoalkyl,3-C6trialkylsilyl-C1-C5alkyl, panels1-C2alkyl, heteroaryl1-C2alkyl, venoxis1-C2alkyl, heterokaryosis1-C2alkyl, phenyl or heteroaryl, benzyloxy or phenoxy, and benzyl and phenyl groups may be substituted with halogen, nitro, cyano, amino, dimethylamino, hydroxy, methoxy, ethoxy-, methylthio-, ethylthiourea, formyl, acetyl, propionyl, carboxyla, C1-C5alkoxycarbonyl or 1- or2haloalkyl; and

R37stands With1-C8alkyl, C1-C8haloalkyl,1-C8cianelli,1-C8nitroalkyl,1-C8aminoalkyl,2-C5alkenyl,2-C5haloalkyl,3-C8cycloalkyl,1-C5alkylamino-C1-C5alkyl, C2-C8dialkylamino-C1-C5alkyl, C3-C7cycloalkyl-C1-C5alkyl, C2-C4alkoxyalkyl,4-C6alkenylacyl,4-C6alkyloxyalkyl,2-C4alkylthiomethyl,1-C4alkylsulfonyl-C1-C2alkyl, C1-C2alkylsulfonyl-C1-C2alkyl, C2-C4alkylidenes-C1-C2alkyl, C1-C5alkylsulphonyl-C1-C2alkyl, C1-C5alkoxycarbonyl-C1-C2alkyl, C1-C5aminocarbonyl-C1-C2alkyl, C2-C8dialkylaminoalkyl-C1-C2alkyl, C1-C5alkylcarboxylic-C1-C2alkyl, C2-C5alkylsulphonyl-(C1-C2alkyl)aminoalkyl,3-C6trialkyl-C1-C5alkyl, panels1-C2alkyl, heteroaryl1-C2alkyl, venoxis1-C2alkyl, heterokaryosis1/sub> -C2alkyl, phenyl or heteroaryl, benzyloxy or phenoxy, and benzyl and phenyl groups may be substituted with halogen, nitro, cyano, amino, dimethylamino, hydroxy, methoxy, ethoxy-, methylthio-, ethylthiourea, formyl, acetyl, propionyl, carboxyla,1-C2alkoxycarbonyl or1- or2haloalkyl; or R37stands With1-C8alkylsulphonyl.

Especially preferred are such compositions according to the invention, in which in the formula I R30, R31, R32and R33each independently of one another denotes hydrogen, C1-C8alkyl, C1-C8haloalkyl,2-C5alkenyl,2-C5haloalkyl,3-C8cycloalkyl,3-C7cycloalkyl-C1-C2alkyl, C2-C4alkoxyalkyl, phenyl, heteroaryl, panels1-C2alkyl, heteroaryl1-C2alkyl, venoxis1-C2alkyl, heterokaryosis1-C2alkyl;

R34, R35and R36each independently of one another denotes hydrogen, C1-C8alkyl, C1-C8haloalkyl,2-C5alkenyl,2-C5haloalkyl,3-C8cycloalkyl,3-C7cycloalkyl-C1-C2alkyl, C2-C4alkoxyalkyl, phenyl, heteroaryl,panels 1-C2alkyl, heteroaryl1-C2alkyl, venoxis1-C2alkyl, heterokaryosis1-C2alkyl, C1-C6alkoxy, C1-C3alkylamino or di(C1-C3alkyl)amino; and

R37represents C1-C8alkyl, C1-C8haloalkyl,2-C5alkenyl,2-C5haloalkyl,3-C8cycloalkyl,3-C7cycloalkyl-C1-C2alkyl, C2-C4alkoxyalkyl, phenyl, heteroaryl, panels1-C2alkyl, heteroaryl1-C2alkyl, venoxis1-C2alkyl, heterokaryosis1-C2alkyl, C1-C6alkoxy, C1-C3alkylamino, di(C1-C3alkyl)amino or1-C8alkylsulphonyl.

Among the compositions according to the invention particularly preferred are compositions that contain as have a weed-killing activity component mixture of compounds of formula I and synergistic activity of a quantity of at least one herbicide selected from the group comprising diclofop-methyl, fluazifop-P-butyl, quizalofop-P-ethyl, propaquizafop, clodinafop-P-propargyl, cyhalofop-butyl, fenoxaprop-P-ethyl, haloxyfop-methyl, haloxyfop-aliatel, sethoxydim, aloxide, clethodim, clefoxydim, cycloxydim, tepraloxydim is, the tralkoxydim, butoxide, amidosulfuron, azimsulfuron, enculture-methyl, chlorimuron-ethyl, chinaculture, chlorsulfuron, chlorimuron, cycloaliphatic, atomiculture-methyl, ethoxysulfuron, flazasulfuron, flupyrsulfuron, imazosulfuron, itselffrom (CAS RN 144550-36-7 and 185119-76-0), metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, pyrazosulfuron-ethyl, sulfosulfuron, rimsulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triflusulfuron-methyl, prosulfuron, flucarbazone, tritosulfuron (CAS RN 142469-14-5), imazethapyr, imazamethabenz, imazamethabenz, imazaquin, imazamox, imazapyr, pyrithiobac sodium, Perminova, bispyribac sodium, atrazine, botrell, Simazine, simetryn, terbutryn, terbutylazine, Dimexidum, Isoproturon, chlortoluron, Diuron, damron, fluometuron, linuron, methabenzthiazuron, glyphosate, sulfosate, glufosinate, nitrofen, bifenox, acifluorfen, lactofen, oxyfluorfen, idoxifene, fluoroglycofen, fomesafen, galasoft, azafenidin (CAS RN.-68049-83-2), bestindian (CAS RN 158755-95-4), butoverall (CAS RN 158755-95-4)=CGA 2768S54, carfentrazone-ethyl, cinidon-ethyl (CAS RN 142891-20-1), flumiclorac-pentyl, flumioxazin, fluthiacet-methyl, oxadiargyl (CAS RN 39807-15-3), oxadiazon, pentoxide (CAS RN 110956-75-7), sulfentrazone, flatlet (CAS RN 174514-07-9), pyraflufen-ethyl, alachlor, acetochlor, butachlor, dimethachlor, dimethenamid, S-DIMET named, metazachlor, metolachlor, S-metolachlor, pretilachlor, propachlor, propisochlor, tanishlar, pentamid (CAS RN 106700-29-2), 2,4-D, fluroxypyr, MSRA, MSR, MSRV, trichlopyr, metropop-P, hexazinone, metamitron, metribuzin, oryzalin, pendimethalin, trifluralin, ozone chloride, norflurazon, chlorpropham, desmedipham, phenmedipham, propham, mefenacet, fluthiacet, butyl, cycloate, diallate, EPTC, asbroker, molinet, prosulfocarb, thiobencarb, triallate, phentramin (CAS RN 158237-07-1), cafestol, dicamba, picloram, diflufenican, propanil, bromoxynil, dichlobenil, ioxynil, sulcotrione, mesotrione (CAS RN 104206-82-8), isoxaflutole, isoxaflutole (CAS RN 141112-06-3), flucarbazone (CAS RN 181274-17-9), propoxycarbazone (CAS RN 145026-81-9 and 181274-15-7 (sodium salt)), foramsulfuron (CAS RN 173159-57-4), penoksulam (CAS RN 219714-96-2), trifloxysulfuron (CAS RN 145099-21-4 and 199119-58-9 (sodium salt)), piritramid (CAS RN 135186-78-6), trifloxysulfuron (CAS RN 145099-21-4 and 199119-58-9 (sodium salt)), piritramid (CAS RN 135186-78-6), flutter-ethyl (CAS RN 188489-07-8), proplusr (CAS RN 190314-43-3), PERCHLORYL (CAS RN 158353-15-2), inflamed (CAS RN 113604-08-7), picolinafen (CAS RN 137641-05-5), nicarbazin (CAS RN 129909-90-6), flutter-ethyl (CAS RN 188489-07-8), proplusr (CAS RN 190314-43-3), PERCHLORYL (CAS RN 158353-15-2), inflamed (CAS RN 113604-08-7). picolinafen (CAS RN 137641-05-5), nicarbazin (CAS RN 129909-90-6), florasulam, dicloflam (CAS RN 145701-21-9), florasulam, flumetsulam, metosulam, amitrol, belforest, bentazon, cinmetacin, klom the zones, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, indianian, isoxaben, oxacyclobutane (CAS RN 153197-14-9), peridot, perinatal (CAS RN 40020-01-7), quinchlorac, quinmerac, tridiphane and temprary CAS RN denotes the serial number in the Chemical Abstracts.

The composition of the invention preferably contain

a) a herbicide of formula I in combination with:

b) with synergistic herbicide activity and the number of the second herbicide according to the invention,

the antidote and

g) oil Supplement.

Of the synergistic activity of the herbicides (b) are preferred representatives of the class of sulfonylureas and phenoxybenzamine acids, especially preferred herbicide is, for example, clodinafop-propargyl described in The Pesticide Manual, 11th ed., British Crop Protection Council, registration No. 147, and triasulfuron described in The Pesticide Manual, 11th ed., British Crop Protection Council, registration No. 723. Especially preferred antidote to the composition of the invention is logintest-mexyl. As an acceptable oil supplements are preferred according to the invention are MERGE® and Actiprom®.

Unless otherwise stated, the above-mentioned components, which are compounds of formula I described in The Pesticide Manual, eleventh ed., 1997, WSRC. Components representing the joint is of formula 1, if necessary, you can also prisutstvuet in the form of their esters or salts, as listed, for example, in The Pesticide Manual, eleventh ed., 1997, WSRC. Butoverall described in US-A-5.183.492. Petaled has a registration number CAS 106700-29-2. Mutation described in US-A-5006158.

The composition of the invention may also include salts of the compounds of formula I which may be formed with acids. Acceptable acid to obtain an acid additive salts are both organic and inorganic acids. Examples of such acids include hydrochloric acid, Hydrobromic acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, propionic acid, butyric acid, valeric acid, oxalic acid, malonic acid, fumaric acid, organic sulfonic acid, lactic acid, tartaric acid, citric acid and salicylic acid. Salts of compounds of formula I which are acidic hydrogen are also alkali metal salts, for example sodium and potassium salts; salts of alkaline-earth metals, for example calcium salts and magnesium; ammonium salts, including unsubstituted ammonium salts and mono - or polyamidine ammonium salts or salts of other organic nitrogenous bases. Preferred soleobrazutaya substances from hydroxides of alkali metals and hydroxides of the Christmas-earth metals preferably include the hydroxides of lithium, sodium, potassium, magnesium or calcium, but especially preferred are the hydroxides of sodium or potassium.

Examples of amines which are suitable for the formation of ammonium salts are not only ammonia, and primary, secondary and tertiary C1-C18the bonds alkylamines,1-C4hydroxyethylamine and C2-C4alkoxyalkyl, for example, 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, methylethylamine, 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, for example, pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, Hinkley and azepine; primary arylamines, for example, anilines, methoxyaniline, ethoxyaniline, ortho-, meta-, para-toluidine, phenylenediamine, benzidine, naphthylamines and ortho-, meta-, para-chloraniline; but especially preferred are triethylamine, Isopropylamine and Diisopropylamine.

If you use the original organization of the achiral products, asymmetrically substituted compounds of formula I obtained according to the processes described in the present description, as a rule, take the form of racemates. Stereoisomers can be divided on the basis of their physico-chemical properties using known techniques such as fractionated crystallization followed by the formation of salts with optically pure bases, acids or complexes of metals, or by chromatographic techniques such as liquid chromatography high pressure (ghvd) on the cellulose acetate. In the context of the present description by "compounds of formula I" is understood as concentrated and optically pure forms of stereoisomers according to the invention and the racemates and diastereoisomers. If not specifically mentioned individual optical antipodes, it should be understood that the formula of the invention relates to racemic mixtures which are obtained from POM is using this method of receipt. If there is aliphatic double bond C=C, there may be geometric isomerization.

The compounds of formula I can also, depending on the nature of the substituents be present as geometrical and/or optical isomers and mixtures of isomers and tautomers and mixtures of tautomers. For example, the compounds of formula I in which G represents hydrogen may be present in the form of tautomers, in the specified state equilibrium:

When G has a value other than hydrogen, and Z represents a group Z1or Z3or when G has a value other than hydrogen, and Z2is asymmetrically substituted, condensed or linked through spirostane, the compounds of formula I may be present as isomer of formula Id

Methods for obtaining compounds other than the compounds of formula I of the present invention in relation to the values of the substituents R4and R5described, for example, in WO 96/21652. The compounds of formula I of the present invention can be obtained by using processes similar to those described in WO 96/21652.

The compounds of formula II

where R1, R3, R4and R5have the meanings specified for formula I, is used as the outcome is s products of such processes, can be obtained, for example, by reacting the compounds of formula III

where R is a C1-C6alkyl, C1-C6haloalkyl, preferably methyl, ethyl or trichlorethyl, and R1and R3have the meanings specified for formula I, in an inert organic solvent, optionally in the presence of a base, with a compound of formula IV or IVa

where R4and R5have the meanings specified for formula I. Other processes of obtaining, using which it is possible to obtain the compounds of formula II, as described, for example, in WO 92/16510.

The compounds of formula III are either known or can be obtained using known methods. Methods for obtaining compounds of formula III and their interaction with hydrazines described, for example, in WO 97/02243. The compounds of formula III in which R represents a C1-C6alkyl, C1-C6haloalkyl, preferably methyl, ethyl or trichlorethyl and R1, R2and R3have the meanings specified for formula I, can be obtained using similar methods known to the person skilled in the art. For example, the compounds of formula III in which R represents a C1-C6alkyl or C1-C6haloalkyl, preferably methyl, ethyl or trichlorethyl, and R1, R2and R3ka is each independently from each other represents C 1-C4alkyl, C2-C4alkenyl or2-C4quinil, can be obtained using the method of cross combinations, described by Stille (J.K.Stille, Angew. Chem. 1986. 98, 504-519), Sonogashira (.Sonogashira and others, Tetrahedron Lett. 1975, 4467-4470), Suzuki (N.Miyaura, A.Suzuki, Chem. Rev. 1995, 95, 2457-2483) or Heck (R.F.Heck, Org. React. 1982, 27, 345-390), and optional subsequent hydrogenation. This process is illustrated in the following reaction scheme:

Compounds of formulas IV and IVa are either known or can be obtained using methods similar to the known. Methods for obtaining compounds of formula IV are described, for example, in WO 95/00521. These compounds can be obtained, for example, by heating the compounds of formula V

where R42denotes hydrogen, C1-C4alkyl, C1-C6alkoxy, C1-C6haloalkoxy or benzyloxy, preferably hydrogen, methyl, methoxy, ethoxy, trichlorethane, tert-butoxy or benzyloxy, and R4and r5have the meanings specified for formula I, in an inert solvent in the presence of base or acid. The compounds of formula V in which R42denotes hydrogen, C1-C4alkyl, C1-C6alkoxy, C1-C6haloalkoxy or benzyloxy, preferably hydrogen, methyl, methoxy, ethoxy, trichlorethane, tert-butoxy or gasoline is hydroxy, and R4and R5have the meanings specified for formula I, can be obtained, for example, by reacting the compounds of formula VI

where R42denotes hydrogen, C1-C4alkyl, C1-C6alkoxy, C1-C6haloalkoxy or benzyloxy, preferably hydrogen, methyl, methoxy, ethoxy, trichlorethane, tert-butoxy or benzyloxy, in the presence of a base and an inert solvent, with a compound of formula VII

where Y denotes halogen, alkyl/arylsulfonate-OSO2R43preferably bromine, chlorine, iodine, mesilate (R43=CH3), triplet (R43=CF3or tosylate (R43= para-tolyl), and Z1, Z2and Z3have the meanings specified for formula I. In formula VII, the free valence of the groups Z1, Z2and Z3in each case linked to the group y in the Compounds of formula VI and VII are known or can be obtained analogously to the methods known to the person skilled in the art. The compounds of formula IV in which R4and R5together denote the group of Z2i.e.-C-R14(R15)-C-R16(R17)-O-C-R18(R19)-C-R20(R21)-, where R14, R15, R16, R17, R18, R19, R20and R21denote hydrogen, can be obtained, for example, according to the following reaction scheme:

The final products of formula I can be there a generally accepted method by concentration and/or evaporation of the solvent and by crystallization or trituration of the solid residue in solvents in which they are not completely soluble, such as ethers, alkanes, aromatic hydrocarbons or chlorinated hydrocarbons, or can be purified by chromatography. Salts of compounds of formula I can be obtained well-known method. Such methods of production are described, for example, in WO 96/21652.

Examples:

Example P1: Getting

The solution containing 177,6 g methanesulfonanilide in 400 ml of diethyl ether, is added dropwise over 1 h to a cooled to -10°With the solution containing of 80.6 g (0,76 mole) of diethylene glycol and 159,9 g (1,58 mole) of triethylamine in 1500 ml of diethyl ether, maintaining the temperature below 5°C. After stirring for 30 min at a temperature of 0°With cooling stop. After 2 h, add 12 ml of triethylamine and 12 ml of methanesulfonanilide at a temperature of 20°and the mixture is stirred for a further 4 hours the Resulting white suspension is then transferred to a vacuum filter and the residue is washed three times with 300 ml of diethyl ether. The filter residue is dissolved in 2000 ml of ethyl acetate and the suspension premesis the Ute for 30 min at room temperature and again filtered. The obtained filtrate is concentrated by evaporation and the residue used in the next reaction without further purification. Get 216,5 g of the desired crude product (1) in the form of white crystals.

Example P2:

The solution containing 68,78 g (0,30 mol) of the compound (2) in 140 ml of dimethylformamide, is added dropwise within 30 min to a cooled to 5°With a suspension containing of 23.9 g (of 0.60 mole) of 60%sodium hydride in 500 ml of dimethylformamide. Cooling stop and carry out the stirring until a temperature of the reaction mixture 20°C. the mixture is Then rapidly heated to a temperature of 30-40°With the goal of complete elimination of hydrogen.

After cooling to a temperature of 0-5°With added dropwise over 30 min a solution containing 80 g (0,305 mol) (1) in 160 ml of dimethylformamide, keeping the temperature at 0 to 5°C. After termination of the cooling and stirring for 3 h at room temperature and for 45 min at a temperature of about 40°the reaction mixture is poured into a mixture containing a saturated solution of ammonium chloride, ice and methyl tert-butyl ether; the phases are separated and then the organic phase washed with water (twice). After drying the organic phase over sodium sulfate, concentration and evaporation and further drying at a temperature of 40° With the vacuum get 92,2 g (3) in the form of oil is light yellow in color. The crude product used in the next reaction without further purification.

Example P3:

160,5 ml of 33%solution of hydrogen bromide in glacial acetic acid is added dropwise within 30 min to a cooled to 0°With the solution containing of 92.2 g (0,305 mol) of the compound (3) in 1200 ml of diethyl ether. After termination of the cooling and subsequent stirring for 22 h at 20°and With stirring for 27 hours at a temperature of reflux distilled the resulting white suspension is transferred into a vacuum filter; then rinse with diethyl ether and the residue on the filter is then dried over P2O5in vacuum at a temperature of from 50 to 60°C. Receive the product (4) in the form of a solid white color, output 52,9,

Example P4:

10,61 ml (76 mmol) of triethylamine are added to a suspension containing 4.4 g (of 16.5 mmole) of the compound (4) in 175 ml of xylene and carry out degassing (4 × vacuum/argon). The yellow suspension is then heated to a temperature of 60°C and stirred for 3 hours Then add 5,07 g (of 16.5 mmole) of the compound (5) and heated in a bath with a temperature of 140°in order to continuously ward off the excess triethylamine and the resulting ethanol. After 3 h Rea is operating, the mixture is cooled to a temperature of 40° C and poured into 100 ml of a mixture of ice/water. The reaction mixture was alkalinized with aqueous 1 n sodium hydroxide solution and the aqueous phase (containing the product) are washed twice with ethyl acetate. Then after twice washing the organic phase water 1 N. a solution of sodium hydroxide aqueous phase combine remaining cyclen distilled off and the pH of the combined aqueous phases are adjusted by cooling to 2-3 with 4 N. Hcl. Usageprice product is transferred to a vacuum filter, the filter residue washed with water and hexane and the residue on the filter is then dried in a vacuum at a temperature of 60°above the P2O5. Get 4,08 g of solid matter (6)having a melting point of 189-191°C (decomposition).

Example P5:

A catalytic amount of 4-dimethylaminopyridine add to cooled down to 0°With the solution containing 1 g (3.2 mmole) of the compound (6) and 0.65 g (6.4 mmole) of triethylamine in 30 ml of tetrahydrofuran. Then added dropwise 0,49 g (4.1 mmole) of pivaloate. After stirring for 30 min at a temperature of 0°With cooling stop and stirring is carried out for a further 60 minutes and Then the reaction mixture was poured onto saturated aqueous solution of sodium chloride and the organic phase is separated. The organic phase is dried over magnesium sulfate, filtered and conc is jut the process of evaporation. After purification by chromatography and recrystallization from diethyl ether to obtain 1.07 g of the compound (7) with a melting point of 122 to 123°C.

Example P6: Getting

To a solution containing 20 g of dimethyl 2-(2,6-dibromo-4-were)malonic acid (known from WO 96/35664) (52,6 mmole) in 400 ml of toluene (degassed three times, vacuum/argon)add first 36,7 g (0,116 mole) of tributylstannyl, and then 2 g of tetrakis(triphenylphosphine)palladium. Then the reaction mixture is stirred for 9 hours at a temperature of from 90 to 95°C. After filtration through Hyflo filter type and concentration using a rotary evaporator, and after purification by chromatography gain of 15.3 g of compound (8) in the form of a yellow oil, which was used in the next stage without additional purification.

Example P7:

15.2 g of the compound (8)obtained according to example P6, hydronaut using hydrogen in the presence of palladium catalyst (charcoal as a carrier, 7 g of 5%Pd/C) in 160 ml of tetrahydrofuran at a temperature of from 20 to 25°C. After completion of the hydrogenation product is filtered through a Hyflo filter type and the obtained filtrate is concentrated using a rotary evaporator. Gain of 13.7 g of compound (5) in the form of yellow crystals with temperature plavleniyu 47 to 49° C.

Example P8:

and 67.8 g (of 0.59 mol) of methanesulfonamide added dropwise to a cooled to 0-3°With the solution containing 37,1 g (0,28 mol) of CIS-2,5-bis(hydroxymethyl)tetrahydrofuran (12) and to 65.3 g (of 0.65 mole) of triethylamine in 400 ml of methylene chloride, keeping the temperature below 7°C. Then carry out the stirring overnight at a temperature of 20°C. the Resulting white suspension is transferred into a vacuum filter, the residue is washed with methylene chloride and the filtrate is concentrated by evaporation. The residue is dissolved in ethyl acetate, washed with water (twice) and saturated aqueous sodium chloride (once), dried (PA2SO4) and concentrate. Get 72,7 g dimethylated derivative (13) in the form of crude oil, which is used in the next reaction without further purification.

The original product (12) described in the literature: see, for example, .Naemura and others, Tetrahedron Asymmetry, 1993, 4, 911-918.

Example P9:

Working analogously to example obtain P2, using as initial products 21,0 g (of 0.53 mol) of 60%NaH, 58,4 g (0.25 mol) of the compound (2) and 72,5 g (0.25 mole) of dimesilate (13) in the total volume of 840 ml of dimethylformamide, to obtain the compound (14) in the form of untreated small brown. After purification by chromatography receive of 53.7 g of pure joint is (14) in the form of a solid white color with temperatures ranging from 81 to 83° C.

Example P10:

Working analogously to example obtain P3, using as initial products of 53.5 g (0,16 mol) of the compound (14) in 800 ml of diethyl ether and 90 ml of 33%solution of hydrogen bromide in concentrated acetic acid to obtain 36.5 g of bicyclic hydrazine (15) in the form of a solid substance with a melting point 262 to 264°C.

Example P11:

Working analogously to example getting P4, using as initial products 0,105 mol of malonate (9) and 30.4 g (0,105 mole) of hydrazine (15), receive and 29.7 g of compound (16) in the form of a solid substance with a melting point 287°C.

Example R:

Working analogously to example getting P9, using as initial products 1.1 g (3,2 mol) of the compound (16), get 0,83 g Pihlajavesi ether (17) in the form of a solid substance with a melting point 141-143°C.

In the table below, shown as Deputy G formula, the left side of the formula is the place of connection of the oxygen atom of the heterocycle. The other end of the valence patterns are a metal group.

Table 1

The compounds of formula Ie:

is OED. No.R1R3GPhys. data
1.001CH3Och3N 
1.002CH3Och3C(O)C(CH3)3 
1.003CH3Och3C(O)och2CH3 
1.004CH2CH3CH3NtPL182-185°
1.005CH2CH3CH3C(O)C(CH3)3tPL110-113°C
1.006CH2CH3CH3C(O)och2CH3 
1.007CH2CH3CH2CH3NtPL189-191°
1.008CH2CH3CH2CH3C(O)C(CH3)3tPL122-124°
1.009CH2CH3CH2CH3C(O)och2CH3tPL114-116°
1.010 CH=CH2CH3NtPL165-170°

Conn. No.R1R3GPhys. data
1.011CH=CH2CH3C(O)C(CH3)3tPL111-113°
1.012CH=CH2CH2CH3N 
1.013CH=CH2CH=CH2N 
1.014CH=CH2CH=CH2C(O)C(CH3)3 
1.015C≡CHCH3NtPL179-184°
1.016C≡CHCH3C(O)C(CH3)3tPL109-111°
1.017C≡CHCH3C(O)och2CH3 
1.018C≡CHCH2CH3NtPL189-193°
1.019C≡CHCH2CH3C(O)C(CH3 )3 
1.020C≡CHCH2CH3C(O)och2CH3 
1.021C≡CHC≡CHNtPL300°C
1.022C≡CHC≡CHC(O)C(CH3)3tPL183-185°
1.023C≡CHC≡CHC(O)och2CH3 
1.024C≡CHCH=CH2N 
1.025With≡CLO3CH3NtPL179-181°
1.026With≡CLO3CH3C(O)C(CH3)3tPL128-129°C
1.027With≡CLO3CH3C(O)och2CH3 
1.028With≡CLO3CH2CH3N 
1.029With≡CLO3CH2CH3C(O)C(CH3)3 
1,030With≡CLO3 With≡CLO3N 
1.031With≡CLO3With≡CLO3C(O)C(CH3)3 
1.032CH2CH2CH3CH3NtPL136-138°
1.033CH2CH2CH3CH3C(O)C(CH3)3tPL65-67°
1.034CH2CH2CH3CH3C(O)och2CH3 
1.035CH2CH2CH3CH2CH3N 
1.036CH2CH2CH3CH2CH2CH3N 
1.037CH2CH2CH3CH2CH2CH3C(O)C(CH3)3 

td align="left"> wax
Conn. No.R1R3GPhys. data
1.038CH2CH2CH3CH2CH2CH3 C(O)och2CH3 
1.039CH2CH2CH3C≡CHN 
1.040CH(CH3)2CH3NtPL214-216°C
Mos.%CH(CH3)2CH3C(O)C(CH3)3tPL148-151°C
1.%CH(CH3)2CH2CH3N 
1.043CH(CH3)2C≡CHN 
Ob.%CH3N 
1.045CH2CH3N 
1.046C≡CHN 
1.047CH2CH=CH2CH3N 
1.048CH2CH=CH2CH2CH3N 
1.049 CH2CH=CH2C≡CHN 
1.050CH2CH2CH2CH3CH3N 
1.051CH3About-CH2CH3N 
1.052CH3About-CH2CH3C(O)C(CH3)3 
1.053CH2CH3CH2CH3SO2CH(CH3)2 
1.054CH2CH3CH2CH3SO2CH3crystal
1.055CH2CH3CH2CH3SO2CH(CH3)2 
1.056CH2CH3CH2CH3SO2CF3 
1.057CH2CH3CH2CH3SO2CH2CH3 
1.058CH2CH2CH2CH3SO2CH2CH(CH3)2
1.059CH2CH3CH2CH3SO2CH2CH2Cl 
1.060CH2CH3CH2CH3SO2CH=CH2wax
1.061CH2CH3CH2CH3SO2CH2CH2Br 

Conn. No.R1R3GPhys. data
1.062CH2CH3CH2CH3F.: 204-205
Blade 1.063CH2CH3CH2CH3F.: 203-204
1.064CH2CH3CH2CH3SO2-benzilF.: 157-158
1.065CH2CH3CH2CH3wax
1.066CH2CH3CH2CH3SO2CH2CH2CH2CL wax
1.067CH2CH3CH2CH3F.: 126
1.068CH2CH3CH2CH3F.: 146
1.069CH2CH3CH2CH3F.: 82-85
1.070CH2CH3CH2CH3SO2CH2CH=CH2 
1.071C≡CHCH2CH3SO2CH3 
1.072C≡CHCH2CH3SO2CH(CH3)2 

Conn. No.R1R3GPhys. data
1.073With≡SNCH2CH3SO2CH2CH2Cl 
1.074With≡SNCH2CH3SO2CF3 
1.075 With≡SNCH2CH3SO2CH=CH2 
1.076With≡SNOch3-NtPL202-204
1.077With≡SNOch3C(O)C(CH3)3tPL204-206
1.078With≡Si(CH3)3Och3C(O)C(CH3)3tPL169-171
1.079With≡Si(CH3)3Och3-NtPL173-174
1.080VGOch3-NtPL217-219
1.081VGOch3C(O)C(CH3)3tPL173-175
1.082CH2CH3CH2CH3C(O)C(CH3)2tPL122-124°C
   CH2CH3 
1.083CH2CH3CH2CH3SOP(CH2CH3)2tPL82-84
1.084CH2CH3 C(O)CH3C(O)C(CH3)2tPL138-139°C
   CH2CH3 
1.085CH2CH3C(O)CH3 
1.086CH2CH3C(O)CH3 
1.087CH2CH3C(O)CH3 
1.088CH2CH3C(O)CH3 

The invention relates also to method selective weed control in crops of useful plants, which provides processing of useful plants, their seeds or seedlings or their acreage and herbicide effective amount of a herbicide of formula I, b) with herbicide synergistic activity amount of at least one herbicide selected from the class phenoxybenzamine acids, hydroxylamines, sulfonylureas, imidazolinones, pyrimidines, triazines, ureas, PPO, chlorate the reaction PHENOXYACETIC acids, triazines, dinitroanilines, azinones, carbamates, oxoazetidin, thiolcarbamate, salmochelin, benzoic acids, anilides, NITRILES, trions and sulfonamides, and of these herbicides, as amitrol, belforest, bentazon, cinmetacin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, indianian, isoxaben, oxacyclobutane, peridot, perinatal, quinchlorac, quinmerac, tridiphane, planrep and glufosinate; and optionally C) are effective for preventing harmful effects of herbicide amount of a safener selected from the group comprising logintest, cation, such as alkali metal, alkaline earth metal, sulfone or ammonium logintime, logintest-mexyl, mefenpyr, cation, such as alkali metal, alkaline earth metal, sulfone or ammonium mefenpyr, and mefenpyr-diethyl; and/or g) additive, including oil of vegetable or animal origin, a mineral oil, it alkalemia esters or blends of these oils and derivatives of oils.

Cultivated plants that can be protected from the harmful effects of the above herbicides with safener selected from the group comprising logintest, cation, such as alkali metal, alkaline earth metal, sulfone or ammonium logintime, logintest-mexyl, mefenpyr, cation, such as SELA the Noah metal, alkaline-earth metal, sulfone or ammonium mefenpyr, and mefenpyr-diethyl, preferably are cereals, cotton, soybeans, sugar beets, sugar cane, plantation crops, rape, maize and rice, more preferably corn and cereals. In addition, it should be understood that useful culture can also define culture, have created a resistance to certain herbicides or classes of herbicides by using conventional breeding methods or genetic engineering techniques, such as IMI-corn, Poast Protected corn (tolerance methoxide). Liberty Link corn, .t./Liberty Link corn, IMI/Liberty Link corn, IMI/Liberty Link /.t.-corn, Roundup Ready corn and Roundup Ready/B.t corn.

Weeds must be destroyed, can be either two-or preferably monocotyledonous weeds such as Avena, Agrostis, Phalaris, Lolium, Bromus, Alopecurus, Setaria, Digitaria, Brachiaria, Echinochloa, Panicum, Sorghum hal./the bic., Rottboellia, Cyperus, Brachiaria, Echinochloa, Scirpus, Monochoria and Sagittaria, and dicotyledonous weed plants such as Sinapis, Chenopodium, Stellaria, Galium, Viola, Veronica, Matricaria, Papaver, Solanum, Abutilon, Sida, Xanthium, Amaranthus, Ipomoea and Chrysanthemum.

Under planted areas" should be understood areas of soils that are already planted with cultivated plants or their seeds, as well as areas intended for planting these crops.

Depending on the ultimate goal of the antidote according to the invention can be used for pre-treatment of seeds of cultivated plants (seed dressing or treatment of seedlings), or it can be incorporated into the soil before or after sowing. In addition, it may be made separately or together with the herbicide and oil additive post-emergent plants. Therefore, processing plants or seeds antidote in principle can be achieved regardless of the time of herbicide treatment. However, the plant also can be treated by simultaneous application of herbicide, oil additives and antidote (for example, in the form of a tank mixture (mixture prepared in the same tank)). Consumption rates antidote regarding herbicide primarily depend on the type of processing. For processing crops in unprotected soil, which is carried out either using a mixture prepared in the tank, which includes a combination of safener and herbicide, or by separately making the antidote and herbicide, the ratio between the herbicide and the antidote, as a rule, is from 100:1 to 1:10, preferably from 20:1 to 1:1. For processing crops in unprotected soil, usually contribute from 0.001 to 1.0 kg/ha, preferably from 0.001 to 0.25 kg of safener/ha

The consumption rate of the herbicide, as a rule, is from 0.001 to 2 kg/ha, but preferably 0.005 to 1 kg/ha

In the composition according to the invention, the mass ratio of the compounds of formula I and the second herbicide is from 1:100 to 1000:1.

In the composition according to the invention the amount of oil additives usually is from 0.01 to 2%, calculated on the weight of the mixture for spraying. Oil additive can, for example, to enter the tank for spraying in the desired concentration after preparation of the mixture for spraying.

Preferred oil additives are mineral oils or vegetable oils, such as rapeseed oil, olive oil or sunflower oil, alkalemia esters of oils of vegetable origin, such as methyl derivatives, or an oil of animal origin, such as fish oil or beef margarine.

Particularly preferred oil additives represent alkalemia esters of higher fatty acids (C8-C22), especially methyl derivatives of fatty12-C18acids, for example, methyl esters of lauric acid, palmitic acid and oleic acid. These esters are known as meilleur (CAS 111-82-0), metralleta (CAS 112-39-0) and methyl oleate (CAS 112-62-9).

The administration and operation of oil additives can be improved by combining them with surfactants, such as nonionic, anionic or cationogenic surfactants. Examples of acceptable anionic, nonionic and cationogenic surfactants described in WO 97/34485 on page 7 and 8.

The preferred surface is but-active agents are anionic surfactants of the type dodecylbenzensulfonate, especially their calcium salts, and nonionic surfactants of the type ethoxylates fatty alcohol. Especially preferred are ethoxylated fatty12-C22alcohols having a degree of amoxilonline from 5 to 40. Examples of commercially available preferred surfactants are substances belonging to the types Genapol (Clariant AG, Muttenz, Switzerland).

The concentration of surfactants in terms of the total weight of the additive is usually from 1 to 30 wt.%.

Examples of oil additives, which are blends of oils or mineral oils or derivatives thereof with a surface-active substances are Edenor ME SU®, Emery 2231® (Henkel Tochtergesellschaft Cognis GMBH, Germany, Turbocharge® (Zeneca Agro, Stoney Creek, Ontario, Canada) or most preferably Actipron® (BP Oil UK Limited, UK).

The introduction of organic solvent in the mixture of oil additives/surfactants may also further strengthen its action. Acceptable solvents are, for example, the solvent of Solvesso type® (ESSO) or Aromatic Solvent® (Exxon Corporation).

The concentration of these solvents may be from 10 to 80% based on the total weight.

Such oil supplements, which are also described for example in US-A-4834908, are particularly preferred for the composition of of the bretania. Particularly preferred oil additive known as the MERGE®, can be obtained from BASF Corporation, and it is generally described, for example, in US-A-4834908 in column 5 as an example, SOS-1. Another oil additive, which is preferred according to the invention, is SCORE® (Novartis Crop Protection Canada.)

Processing using the proposed composition can be done all acceptable methods, for example, to apply on predsjedava stage, post-harvest stage and for seed treatment.

For seed, as a rule, use from 0.001 to 10 g of safener/kg of seed, preferably from 0.05 to 6 g of safener/kg of seeds. If the antidote is applied in liquid form shortly before the time of sowing, for more effective suction should be applied solutions antidote containing the active substance in a concentration of from 1 to 10000 ppm million, preferably from 100 to 1000 ppm million

For processing, it is preferable to use the antidotes according to the invention or a combination of these antidotes with herbicides of formula I and oil additives together with auxiliary substances commonly used in cooking techniques preparative forms, for example, obtaining mulgirigala concentrates coating pastes, ready to use sprayable or dilutable solutions, razbavlyali, wettable powders, soluble powders, Farrukh Dustov, granules or microencapsulated drugs.

Such compositions are described, for example, in WO 97/34485 on p.9-13. The composition is prepared by usual method, for example, by homogeneous mixing and/or grinding of active substances together with a solid or liquid excipients, for example solvents or solid carriers. In addition, to obtain compositions may optionally be used surface-active substances (surfactants). Solvents and solid carriers which can be used for this purpose, see, for example, in WO 97/ 34485 on page 6.

Depending on the nature of the active substance of the formula I, which is included in the composition, suitable surfactants are nonionic, cationogenic and/or anionic surfactants and mixtures of surfactants with high emulsifying, dispersing and wetting properties. Examples of usable anionic, nonionic and cationogenic surfactants are described, for example, in WO 97/34485 on page 7 and 8. In addition, for preparation of the herbicide compositions according to the invention can also be applied surfactants, which are usually used for cooking preparative forms, which, in h is particularly described in: "Mc Cutcheon''s Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood New Jersey, 1981, Stache, H., "Tensid-Taschenbuch", Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash, "Encyclopedia of Surfactants", vol I-III, Chemical Publishing Co., New York, 1980-81.

Herbicide compositions usually contain from 0.1 to 99 wt.%, in particular, from 0.1 to 95 wt.% the mixture of active substances, comprising a compound of formula I, the second synergistic activity of the herbicide and not necessarily the antidote according to the invention, from 0 to 2 wt.% oil additives according to the invention and from 1 to 99.9 wt.%, solid or liquid excipients for formulation and from 0 to 25 wt.%, preferably from 0.1 to 25 wt.% surfactants. Despite the fact that as provided in the sale of the most preferred compositions concentrated compositions, the end user typically uses dilute compositions.

The composition may also contain other additives, such as stabilizers, for example, optionally 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. To make antidotes according to the invention or compositions containing them for protecting cultivated plants from undesired hair what's effects of herbicides of formula I it is possible to apply various methods and technologies, for example, methods described below:

I) seed Dressing

a) seed Treatment composition in the form of a wettable powder containing as active ingredient the antidote according to the invention, by shaking in a vessel until then, until it is distributed evenly over the surface of the seeds (dry processing). With this purpose to process 100 kg of seed use from 1 to 500 g used as an active agent antidotes (4 g to 2 kg of wettable powder).

b) seed Treatment emulgirujushchie concentrate antidotes according to the invention in accordance with the method a) (wet processing).

C) Dressing by immersing the seeds in a mixture containing 100-1000 ppm million antidotes according to the invention for 1-72 hours, leaving them wet or exposing them to further drying (seed soaking).

Seed treatment or processing of germinated seedlings, obviously, are the preferred methods of processing, as the processing of the active substance is completely focused on the target culture. Usually used from 1 to 1000 g of antidote, preferably from 5 to 250 g of safener per 100 kg of seed, however, depending on the method used, which also enables the use of other active ingredients or micronutrients, possible deviations from the specified concentration limits both in big, and in anisou side (the ratio of impregnation).

II) Amendment in the form of a mixture, prepared in the tank (tank mixture)

Apply a liquid composition of a mixture of antidote and herbicide (mutual ratio of from 20:1 to 1:100), the rate of application of herbicide is 0.005 to 5.0 kg/ha In the mixture in the tank, you can add an oil additive, preferably in an amount of from 0.01 to 2 wt.%. These prepared in the same tank mixtures contribute to or after seeding.

III) introducing into the furrow

The antidote in the form of mulgirigala concentrate, wettable powder or granules contribute in an open furrow in which seeds were sown. After closing the furrow herbicide, optionally in combination with an oil additive, apply the usual method for predsjedava stage.

IV) Controlled release of the active substance

The antidote is applied in solution in mineral granular substrates or polymerised granules (urea/formaldehyde) and allowed to dry. Optionally, the pellets can be coated (granules coated), which provides a controlled release of the active substance within a certain period of time.

Preferred compositions are, in particular, the following composition: (% means wt.%; “the mixture of active substances” means a mixture of compounds of formula I with synergistic activity on the second the herbicide and not necessarily with antidotes according to the invention and/or oil additives).

Mulgirigala concentrates:

the mixture of active substances: from 1 to 90%, preferably from 5 to 20%

surfactant: 1 to 30%, preferably from 10 to 20%

carrier liquid: 5 to 94%, preferably 70 to 85%

Dusty:

the mixture of active substances: from 0.1 to 10%, preferably from 0.1 to 5%

solid media: from about 99.9 to 90%, preferably from about 99.9 to 99%

Suspension concentrates:

the mixture of active substances: 5 to 75%, preferably from 10 to 50%

water: 94 to 24%, preferably 88 to 30%

surfactant: 1 to 40%, preferably from 2 to 30%

Wettable powders:

the mixture of active substances: 0.5 to 90%, preferably from 1 to 80%

surfactant: 0.5 to 20%, preferably from 1 to 15%

solid carrier: 5 to 95%, preferably from 15 to 90%

Granules:

the mixture of active substances: from 0.1 to 30%, preferably from 0.1 to 15%

solid media: from 99.5 to 70%, preferably 97 to 85%.

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

Examples of compositions based on mixtures of herbicides and, if necessary antidotes and oil additives (% means mass%)

F1. Mulgirigala concentratesa)b) in)g)
the mixture of active substances5%10%25%50%
Dodecylbenzenesulfonate calcium6%8%6%8%
polietilenglikolya ether of castor oil (36 moles ethyleneoxide links)4%-4%4%
Octylphenoxypolyethoxyethanol ether (7-8 moles ethyleneoxide links)-4%-2%
cyclohexanone--10%20%
a mixture of aromatic hydrocarbons With9-C1285%78%55%16%
Emulsions of any required concentration can be obtained from these concentrates by dilution with water
F2. Solutionsa)b)in)g)
the mixture of active substances5%10%50%90%
1-methoxy-3-(3-methoxypropane)propane- 20%20%-
polyethylene glycol (mol. weight 40020%10%--
N-methyl-2-pyrrolidone--30%10%
a mixture of aromatic hydrocarbons With9-C1275%60%--
The solutions are suitable for application in the form of microdrops
F.3 Wettable powdersa)b)in)g)
the mixture of active substances5%25%50%80%
lignosulfate sodium4%-3%-
sodium lauryl sulfate2%3%-4%
diisobutylaluminum sodium-6%5%6%
octylphenoxypolyethoxyethanol (7-8 moles teleocidin links)-1% 2%-
highly dispersed silicic acid1%3%5%10%
Kaolin88%62%35%-

Active ingredients thoroughly mixed with the adjuvants and the mixture is ground in a suitable mill, receiving wettable powders which can be diluted with water to obtain suspensions of any desired concentration.

F4. Granules coateda)b)g)
the mixture of active substances0,1%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, the solution is sprayed onto the carrier and then the solvent is removed under vacuum.

F5. Granules coateda)b)in)
the mixture of active substances0,1% 5%15%
polyethylene glycol (mol. mass 2001,0%2%3%
highly dispersed silicic acid0,9%1%2%
inorganic media (⊘ 0,1-1 mm), for example, caso3or SiO298,0%92%80%

Finely ground active ingredient is uniformly fed into the mixer to medium, moist glycol, getting dust free granules coated.

F6. Extruded granulesa)b)in)g)
the mixture of active substances0,1%3%5%15%
sodium lignosulphonate1,5%2%3%4%
carboxymethylcellulose1,4%2%2%2%
Kaolin97,0%93%90%79%

The active substance is mixed with the adjuvants and the mixture is ground, moistened with water, ekstragiruyut and then dried in the air stream.

F7. dustya)b) in)
the mixture of active substances0,1%1%5%
Talc39,9%49%35%
kaolin60,0%50%60%

Ready-to-use dusty obtained by mixing the active substances with the carriers and grinding the mixture in a suitable mill.

87%
F8. Suspension concentratesa)b)in)g)
The mixture of active substances3%10%25%50%
ethylene glycol5%5%5%5%
nonylphenolethoxylate (15 moles ethyleneoxide links)-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%
Water79%62%38%

Finely ground active ingredient is uniformly mixed with adjuvants, receiving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.

Often more preferable to make separate preparative forms-based herbicides (optional in combination with an oil additive) and on the basis of antidotes and mix them in water immediately prior to introduction into the machine to make pesticides in the desired mixing ratio in the form of a "tank mixture" (mixture prepared in the same tank). On the basis of herbicides and antidotes can be prepared in various formulations of and immediately before use to bring along in the car to make pesticides in the desired mixing ratio in the form of a "tank mixture" (mixture prepared in the tank) in water, and then to make oil Supplement.

The effectiveness of the compositions according to the invention as herbicides selective action is illustrated in the following examples.

Biological examples

Example B1: Experience in determining the effectiveness on post-harvest stage of plant development

Experimental plants grown in the greenhouse in pots until germination. As the substrate DL the growing use standard soil. At post-harvest stage of the experimental plants or plants grown from seeds treated with the antidote, treated either with herbicides or mixtures of herbicides with antidotes and/or oil additives. Treatment is carried out with the use of emulsion (obtained from mulgirigala concentrate (example F1, C)) of the test compounds. Consumption rates depend on the optimal doses defined in unprotected soil in the greenhouse. The treatment efficiency estimate 2-4 weeks after the start of the experiments (100% take full destruction, 0% - no phyto-toxic action).

As oil additives used ACTIPRON® at a concentration of 0.5% calculated on the weight of the mixture for spraying.

Table B1

Post-harvest herbicide activity against Alopecurus
A mixture of connectionsConcentration in g/haPhyto-toxic effect against Alopecurus %
clodinafop-propargyl + logintest-maxil- + ACTIPRON®40+1040
connection. 1.007 + logintest-mexyl + ACTIPRON®15+3.750
connection. 1.007 + logintest-mexyl + ACTIPRON®30+7.50
connect the s on. 1.007 + logintest-mexyl + ACTIPRON®45+11.250
connection. 1.007+ logintest-mexyl + ACTIPRON®60+150
connection. 1.007 + logintest-mexyl + ACTIPRON®125+31.2540
connection. 1.007 + clodinafop-propargyl + logintest-mexyl + ACTIPRON®15+15+3.7592
connection. 1.007 + clodinafop-propargyl + logintest-mexyl + ACTIPRON®15+20+596
connection. 1.007 + clodinafop-propargyl +30+15+7.594

A mixture of connectionsConcentration in g/haPhyto-toxic effect against Alopecurus %
logintest-mexyl + ACTIPRON®  
connection no. 1.007+ clodinafop-propargyl + logintest-mexyl + ACTIPRON®30+20+7.596
connection. 1.007 + clodinafop-propargyl + logintest-mexyl + ACTIPRON®45 + 15 + 11.2592
connection no. 1.007+ clodinafop-propargyl + logintest-mexyl + ACTIPRON®45 +20+ 11,2596
connection. 1.007+ clodinafop-propargyl + logintest-Mex is l + ACTIPRON® 60+ 15 + 1598
connection. 1.007+ clodinafop-propargyl + logintest-mexyl + ACTIPRON®60+20+ 1599

From these experiments shows that when used as a herbicide clodinafop-propargyl in combination with the safener logintest-maxilom and oil additive ACTIPRON® achieved only 40%level of herbicide activity against Alopecurus with a total consumption rate of the herbicide/antidote 40 g/ha When using the compounds of formula I (on. 1.007) in combination with the safener logintest-maxilom and oil additive ACTIPRON® herbicide activity against Alopecurus not detected when using the 4 studied consumption norms, and found only 40%activity when using the highest consumption rates (125+31,25 g/ha). However, if an invention unexpectedly found that the composition according to the invention, comprising a herbicide of formula I (on. 1.007) in combination with clodinafop-propargyl, antidote logintest-maxilom and oil additive ACTIPRON® leads to almost complete destruction of Alopecurus when using all studied norms of consumption (efficiency level 92-99%).

Similar action identified as oil supplements instead ACTIPRON® use an oil additive MERGE®.

Example B2: Experience in determining the effectiveness on p is kishtawal stage of plant development:

Experimental plants grown in the greenhouse in pots until germination. As a substrate for growing use standard soil. At post-harvest stage of the experimental plants or plants grown from seeds treated with the antidote, treated either with herbicides or mixtures of herbicides with antidotes and/or oil additives. Treatment is carried out with the use of emulsion (obtained from mulgirigala concentrate (example F1, C)) of the test compounds. Consumption rates depend on the optimal doses defined in unprotected soil in the greenhouse. The treatment efficiency estimate 2-4 weeks after the start of the experiments (100% take full destruction, 0% - no phyto-toxic action).

As oil additives use MERGE® at a concentration of 0.7% based on the weight of the mixture for spraying.

Table W

Post-harvest herbicide activity against weeds in wheat, serviced: tralkoxydim:
The mixture of compounds (concentration in g/ha)WheatAgrostisAvenaLoliumSetaria
connection 1.008 (30 g/ha) + logintest-mexyl (8 g/ha) + tralkoxydim (125 g/ha)

connection 1.008 (30 g/ha + logintest-mexyl (8 g/ha) + MERGE + tralkoxydim (125 g/ha)
0



0
95



98
95



98
80



100
80



98

Table V-V it can be concluded that the introduction of an oil additive MERGE® in a mixture comprising two herbicide and one antidote, unexpectedly increases herbicide activity against weeds, without exerting harmful effects on plants.

Test 1

The investigated seeds were grown in the greenhouse in 10 cm pots in standard soil at a ratio of approximately 30 plants or grass from 3 to 6 broadleaf plants per pot up to the stage of 2-3 leaves.

The compound a of the formula

was applied in the amount of 7.5, 15 and 30 g of active substance per hectare of emulsion concentrate 3 repetitions on the studied species. Each mixture of the herbicides were applied at a dose of between 5 and 800 g of active substance per hectare in a single repetition for the analyzed plant. Processing, dissolution of RO water (deionized by reverse osmosis methods) was carried out using a spray volume of 200 l/ha Treated foliage of grasses and broadleaf weeds with what ispolzovaniem caterpillar spray with one calibrated tip flat spray (11002VS), which is typically used for applying herbicides. After spraying, the plants were placed in a cold greenhouse niche with temperature 12/16°C. Visual assessment of % herbicide effect was carried out after 21 days after treatment (0 = no effect and 100 = total loss). Data for one connection And that cover more than 3 repetitions presented in a table with the results. After evaluating the observed results were compared with the expected results using the method of "Colby". To determine the synergistic effect used the formula: "Expected" result for (a+b)-(AB/100), where a and b are the observed results for a and b (Colby 1967).

These data are summarized in table 1 [ALOMY (Alopecurus myosuroides), LOLMU (Lolium muliflorum), SETVI (Setaria viridis), STEME (Stellaria media). The observed results (table 1) exceeded the expected results for Colby, and therefore, there is a synergistic effect.

Test 2

The investigated seeds were grown in the greenhouse in 10 cm pots in standard soil at a ratio of approximately 30 plants or grass from 3 to 6 broadleaf plants per pot up to the stage of 2-3 leaves.

The compound a of the formula

was applied in the amount of 7.5 and 15 g of active substance per hectare of emulsion concentrate 3 repetitions on the studied species. Each mixture of herbicides is anaxilas at a dose of between 5 and 400 g of active substance per hectare in a single repetition for the analyzed plant. Processing, dissolution of RO water (deionized by reverse osmosis methods) was carried out using a spray volume of 200 l/ha Treated foliage of grasses and broadleaf weeds using a track sprayer with one calibrated tip flat spray (11002VS), which is typically used for applying herbicides. After spraying, the plants were placed in a cold greenhouse niche with temperature 12/16°C. Visual assessment of % herbicide effect was carried out after 21 days after treatment (0 = no effect and 100 = total loss). Data for one connection And that cover more than 3 repetitions presented in a table with the results.

After evaluating the observed results were compared with the expected results using the method of "Colby". To determine the synergistic effect used the formula: "Expected" result for (a+b)-(AB/100), where a and b are the observed results for a and b (Colby 1967).

These data are summarized in table 2 [ALOMY (Alopecurus myosuroides), LOLMU (Lolium muliflorum), SETVI (Setaria viridis). The observed results (table 2) exceeded the expected results for Colby, and therefore, there is a synergistic effect.

Test 3

The investigated seeds were grown in the greenhouse in 10 cm pots in standard soil in a ratio of about 30, R is Steny grass or from 3 to 6 broadleaf plants per pot up to the stage of 2-3 leaves.

The compound a of the formula

was applied in the amount of 7.5, 15 and 30 g of active substance per hectare of emulsion concentrate 3 repetitions on the studied species. Each mixture of the herbicides were applied at a dose of between 5 and 100 g of active substance per hectare in a single repetition for the analyzed plant. Processing, dissolution of RO water (deionized by reverse osmosis methods) was carried out using a spray volume of 200 l/ha Treated leaves four herbs and four broadleaf weeds using a track sprayer with one calibrated tip flat spray (11002VS), which is typically used for applying herbicides. After spraying, the plants were placed in a cold greenhouse niche with temperature 12/16°C. Visual assessment of % herbicide effect was carried out after 22 days after treatment (0 = no effect and 100 = total loss). Data for one connection And that cover more than 3 repetitions presented in a table with the results.

After evaluating the observed results were compared with the expected results by using the method "Colby". To determine the synergistic effect used the formula: "Expected" result for (a+b)-(AB/100), where a and b are the observed results for a and b (Colby 1967).

These data are summarized in table 3 [ALOMY (Alopecurusmyosuroides), LOLMU (Lolium muliflorum), SETVI (Setaria viridis)]. The observed results exceeded the expected results for Colby, and therefore, there is a synergistic effect.

Test 4

The investigated seeds were grown in the greenhouse in 10 cm pots in standard soil at a ratio of approximately 30 plants or grass from 3 to 6 broadleaf plants per pot up to the stage of 2-3 leaves.

The compound a of the formula

was applied in the amount of 7.5 and 15 g of active substance per hectare of emulsion concentrate 3 repetitions on the studied species. Each mixture of the herbicides were applied at a dose of between 5 and 100 g of active substance per hectare in a single repetition for the analyzed plant. Processing, dissolution of RO water (deionized by reverse osmosis methods) was carried out using a spray volume of 200 l/ha Treated leaves four herbs and four broadleaf weeds using a track sprayer with one calibrated tip with a flat spray.

After spraying, the plants were placed in a cold greenhouse niche with temperature 12/16°C. Visual assessment of % herbicide effect was carried out after 22 days after treatment (0 = no effect and 100 = total loss). Data for one connection And that cover more than 3 repetitions presented in tab is itzá with the results.

After evaluating the observed results were compared with the expected results using the method of "Colby". To determine the synergistic effect used the formula: "Expected" result for (a+b)-(AB/100), where a and b are the observed results for a and b (Colby 1967).

These data are summarized in table 4 [Amaranthus retroflexus), VERPE (Veronica persica)]. The observed results exceeded the expected results for Colby, and therefore, there is a synergistic effect.

Test 5

The investigated seeds were grown in the greenhouse in 10 cm pots in standard soil at a ratio of approximately 30 plants grass for 1 pot or 3 to b broadleaf plants to the stage of 2-3 leaves.

The compound a of the formula

was applied in the amount of 7.5 to 15 g of active substance per hectare of emulsion concentrate 3 repetitions on the studied species. Each mixture of the herbicides were applied at a dose of between 5 and 100 g of active substance per hectare in a single repetition for the analyzed plant. Processing, dissolution of RO water (deionized by reverse osmosis methods) was carried out using a spray volume of 200 l/ha Treated leaves 4 herbs and 4 broadleaf weeds using a track sprayer with one calibrated tip with a flat spray. After sprayed the plants I put in a cold greenhouse niche with temperature 12/16° C. Visual assessment of % herbicide effect was carried out after 22 days after treatment (0 = no effect and 100 = total loss). The data for the connection And cover more than 3 iterations, the values presented in the table. After evaluating the observed results were compared with the expected results using the method of "Colby". To determine the synergistic effect used the formula: "Expected" result for (a+b)-(AB/100), where a and b are the observed results for a and b (Colby 1967).

These data are summarized in table 5 [AMARE (Amaranthus retroflexus), VERPE (Veronica persica)]. The results exceeded the expected results for Colby, and therefore, there is a synergistic effect.

1. Herbicide composition, which in addition to conventional inert excipients for the compositions contain as active substance mixture including

a) herbicide effective amount of the compounds of formula I

where

R1and R3each stands With1-C4alkyl, R4and R5together denote a group

-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)-(Z 2or

-C-R22(R23)-C-R24(R25)-C-R26(R27)-O-C-R28(R29)-(Z3),

where R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28and R29each denotes hydrogen;

G represents hydrogen and- (X2)-X3-R31;

X2and X3each represents oxygen;

R31each represents C1-C10alkyl,

b) with herbicide synergistic activity amount of at least one herbicide selected from the class of sulfonylureas, PHENOXYACETIC acids, and of these herbicides, as florasulam, tralkoxydim, clodinafop-propargyl, fenoxaprop-P-ethyl, trifluralin, pendimethalin, picolinafen, propoxycarbazone, flucarbazone, fluroxypyr, triallate, diflufenican, metosulam, prosulfocarb, ioxynil, bromoxynil.

2. The composition according to claim 1, which additionally contains an effective to prevent harmful effects of herbicide amount of the protective agent (antidote), representing logintest-mexyl.

3. The composition according to claim 1, which additionally contains an additive comprising mineral oil or Akilov the e ester C 8-C22fatty acids in the amount of 0-2 wt.%.

4. The method of combating weeds and herbaceous plants in crops of cultivated plants, which is that cultivated plants, their seeds or seedlings or their habitat are treated with a composition according to claims 1-3.

5. The method according to claim 4, where the cultivated plants are cereals.



 

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