Herbicidal agent

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to herbicidal agent containing effective amount of active compound mixture including a) 2-(2-methoxycarbonylsulfonyl aminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazole-3-one of general formula I 1 or sodium salt thereof; and b) one compound improving resistance of agriculture plants, namely diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-licarboxylate in ratio a/b of 1:0.025-25 pts.

EFFECT: herbicidal agent reducing damage of agriculture plants, in particular cereals.

1 cl, 24 tbl, 2 ex

 

The invention relates to new selective herbicide mixtures of active substances, which contain 2-(2-methoxycarbonyl-phenylcarbonylamino-carbonyl)-4-methyl-5-propoxy-2,4-3H-1,2,4-triazole-3-one and/or its salts, in particular its sodium salt, on the one hand, and at least one improves the compatibility of cultivated plants connection, on the other hand, and can be used with particular success in selective weed control in various useful crops.

Substituted phenolsulfonephthalein-triazolinone known as effective herbicides (see, for example, EP-507 171). The action of these compounds and/or their compatibility with respect to cultural plants, however, do not under all conditions completely satisfactory.

Further, the known mixtures of active compounds from substituted phenolsulfonephthalein-triazolinones and other compounds with herbicide activity to achieve synergistic effects (see DE-A 196 388 87). For these mixtures the properties of the application is also not entirely satisfactory for all conditions. A mixture of 2-(2-trifloromethyl-sulfonylmethane)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazoline-3-one with some of the protective equipment described, furthermore, in EP-A 931 456.

Non-obvious way has now been found that 2-(2-methoxycarbonyl-vinylsulfonylacetamido)-4-methyl-5-is robaxi-2,4-dihydro-3H-1,2,4-triazole-3-one and/or its salt in a joint application with the following, improves the compatibility of cultivated plants compounds (protective equipment/antidotes) explicitly prevent damage to cultivated plants and especially advantageously can be used as a combined preparation, which has wide steps for selective weed control in crops of useful plants, such as grain.

The subject of the invention are selective herbicide means, characterized by the beginning of a mixture of active substances, including

(a) 2-(2-methoxycarbonyl-vinylsulfonylacetamido)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazole-3-one of formula (I)

and/or one or more salts of the compounds of formula (I), in particular the sodium salt,

(b) at least one compound that improves the resistance of cultivated plants, from the following groups: α-(1,3-dioxolane-2-yl-methoxyimino-phenylacetonitrile (oxybutinin), α (cyanoethoxy)-phenylacetonitrile (simerini), 4-chloro-N-(1,3-dioxolane-2-yl-methoxy)-α-Cryptor-acetophenone (floxapen), 4,6-dichloro-2-phenyl-pyrimidine (tenharim), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazin (enoxacin), complex 1-methyl-hexylester 5-chloro-cinoxacin-8-oxy-acetic acid (cloquintocet), 2,2-dichloro-N-(2-oxo-2-(2-propylamino)-ethyl)-N-(2-propenyl)-ndimethylacetamide (DKA-24), 1,8-anhydride naftalofos acid complex is tilby ether 1-(2,4-dichloro-phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid (Finlayson-ethyl), fenilmetilovy ester 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid (Florasol), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidin (furilazole, mon-13900), 4-dichloroacetyl-1-oxa-4-Aza-Spiro[4,5]-decane (AD), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2,dichlor-N-(1,3-dioxolane-2-yl-methyl)-N-(2-propenyl)ndimethylacetamide (BCP-1292), 2,2-dichloro-N,N-di-2-propylacetamide (dichlormid), N-(4-methyl-phenyl)-N'-(1-methyl-1-phenyl-ethyl)-urea (damron), 1-dichloroacetyl-hexahydro-3,3,8A-trimethylpyrrole[1,2-a]-pyrimidine-6-(2H)-he (BAS-145138), N-(2-methoxy-benzoyl)-4-(methylamino-carbylamine)-benzosulfimide and/or compounds defined by the following General formulas

where

R32means hydrogen, C1-C8-alkyl or C1-C6-alkoxy or C3-C6-alkenylamine, substituted C1-C8-alkyl, and

X1means hydrogen or chlorine;

or formula (IIb)

where

E. means nitrogen or Metin;

R38means1-C4-alkyl;

R39means CCl3, phenyl or phenyl substituted by halogen, and

R40and R41independently of one another denote hydrogen or halogen;

or the formula (IIc)

where

R27and R28independently from each other mean a hydrogen or halogen and

R29, R30and r31independently from each other mean With1-C4-alkyl;

or the formula (IId)

where

A2means a group of the formula

R35and R36independently of one another denote hydrogen, C1-C8-alkyl, C3-C8-cycloalkyl,3-C6alkenyl,3-C6-quinil,

or1-C4-alkyl, substituted C1-C4-alkoxy or

or

R35and R36form together With the4-C6-Allenby bridge, which can be broken by oxygen, sulfur, SO, SO2, NH or-N(C1-C4-alkyl)-;

R37means hydrogen or C1-C4-alkyl;

R33means hydrogen, halogen, piano, trifloromethyl, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio,1-C4-alkylsulfonyl, C1-C4-alkylsulfonyl, -COORj, -CONRkRm, -CORn, -SO2-NRkRmor-OSO2-C1-C4-alkyl;

Rgmeans hydrogen, halogen, cyano, nitro, C1-C4-alkyl, C1-C4-halogenated,1-C4-alkylthio,1-C4-alkylsulfonyl, C1-C4-alkylsulfonyl, -COORj, -CONRkRm, -CORn, -SO2NRkRm, -OSO2-C1-C4-alkyl, C1-C6-alkoxy or C1-C6-alkoxy, substituted C1-C4-alkoxy or halogen, With3-C5-alkenylamine or3-C6-alkenylamine, substituted with halogen, or With3-C6-alkyloxy, or

R33and R34together form a3-C4-Allenby bridge which may be substituted with halogen or1-C4-alkyl or C3-C4-alkenylamine bridge which may be substituted with halogen or1-C4-alkyl or C3-C4-acadeniy bridge which may be substituted with halogen or1-C4-alkyl;

R34and Rhindependently of one another denote hydrogen, halogen, C1-C4-alkyl, trifluoromethyl, C1-C6-alkoxy, C1-C6-alkylthio or-COORj;

Rcmeans hydrogen, halogen, nitro, C1-C4-alkyl or methoxy,

Rdmeans hydrogen, halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio,1-C4-alkylsulfonyl,1-C4-alkylsulfonyl, -COORjor-CONRkRm;

Remeans hydrogen, halogen, C1-C4-alkyl, -COORjtriptoreline methoxy, or

Rdand Retogether form3-C4-Allenby bridge;

Rfmeans hydrogen, halogen or1-C4-alkyl;

Rxand Ryindependently of one another denote hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, -COOR38, trifluoromethyl, nitro or cyano;

Rj, Rkand Rmindependently of one another denote hydrogen or C1-C4-alkyl; or

Rkand Rmtogether form4-C6-Allenby bridge, which can be broken by oxygen, NH or-N(C1-C4-alkyl)-;

Rnmeans1-C4-alkyl, phenyl or phenyl substituted by halogen, C1-C4-alkyl, methoxy, nitro or trifluoromethyl;

R38means hydrogen, C1-C10-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, CI-C1-C4-alkylamino-C1-C4-alkyl, halogen-(C1-C8-alkyl, C2-C8alkenyl, halogen-C2-C8alkenyl,3-C8-quinil,3-C7-cycloalkyl, halogen-C3-C7-cycloalkyl, C1-C8-alkylsulphonyl, arylcarbamoyl,3-C7-cycloalkylcarbonyl, benzoyl, unsubstituted or substituted in vanilin the m ring, identically or differently up to three times by halogen, With1-C4-alkyl, halogen-C1-C4-alkyl, halogen-(C1-C4-alkoxy or C1-C4-alkoxy; or furoyl, thienyl; or (C1-C4-alkyl, substituted phenyl, halogenfree,1-C4-alkylphenyl, C1-C4-alkoxyphenyl, halogen-C1-C4-alkylphenyl, halogen-C1-C4-alkoxyphenyl, C1-C6-alkoxycarbonyl,1-C4-alkoxy-C1-C8-alkoxycarbonyl,3-C8-alkanolammonium,3-C8-alkyloxyaryl, C1-C8-alkylthiomethyl,3-C8-alkenylsilanes,3-C8-alkylthiomethyl, carbamoyl, mono-C1-C4-alkylaminocarbonyl, di-C1-C4-alkylaminocarbonyl; or phenylenecarbonyl, unsubstituted or identically or differently substituted up to three times in the phenyl by halogen, C1-C4-alkyl, halogen-C1-C4-alkyl, halogen-C1-C4-alkoxy or C1-C4-alkoxy or simply cyano or nitro-group; or dioxolane-2-yl, unsubstituted or substituted by one or two residues With1-C4-alkyl, or dioxane-2-yl, which is unsubstituted or substituted by one or two residues With1-C4-alkyl or C1-C4-alkyl, substituted by cyano or what agropol, carboxyla or C1-C8-alkylthio-C1-C8-alkoxycarbonyl;

or the compound of formula (IIf)

where

R56and R57independently of one another denote C1-C6-alkyl or C2-C6alkenyl;

or

R56and R57together mean

R58and R59independently of one another denote hydrogen or C1-C6-alkyl; or R56and R57together mean

R60and R61mean independently from each other With1-C4-alkyl, or R60and R61together imply (CH2)5-;

R62means hydrogen, C1-C4-alkyl or

or R55and R57together mean

R63, R64, R65, R66, R67, R68, R69, R70, R71, R72, R73, R74, R75, R76, R77and R78

independently of one another denote hydrogen or C1-C4-alkyl;

or the compound of formula (IIg)

R79means hydrogen or chlorine and

R80means cyano or trifluoromethyl,

or the compound of formula (IIh)

where

R81means hydrogen or methyl, or formula (IIj)

where

R82means hydrogen, C1-C4-alkyl, C1-C4-alkyl, substituted C1-C4the alkyl-X2- or1-C4-halogenation-X2-With1-C4-halogenation, nitro, cyano, -COOR85, -NR86R87, -SO2NR88R89or-CONR90R91;

R83means hydrogen, halogen, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy or C1-C4-halogenoalkane;

R84means hydrogen, halogen or1-C4-alkyl;

U, V, W1and Z4independently of one another denote oxygen, sulfur, C(R92R93, carbonyl, NR94group

where

R102means2-C4alkenyl or2-C4-quinil;

provided that at least one of the ring members U, V, W1or Z4is carbonyl and ring member adjacent to it or this ring members, means the group

moreover, this group meets only once; and

b) two adjacent member ring U and V, V and W1and W1and Z cannot simultaneously denote oxygen;

R95and R96Nezavisimaja from each other mean a hydrogen or C 1-C8-alkyl; or R95and R96together form2-C6-alkylenes group;

A1means R99-Y1- or-NR97R98;

X2means oxygen or-S(O)s;

Y1means oxygen or sulfur;

R99means hydrogen, C1-C8-alkyl, C1-C8-halogenated,1-C4-alkoxy-C1-C8-alkyl, C1-C6-alkenylacyl-C1-C8-alkyl or phenyl-C1-C8-alkyl, and the phenyl ring may be substituted with halogen, C1-C4-alkyl, trifluoromethyl, methoxy group or stands-S(O)s-With3-C6alkenyl,3-C6-halogenoalkanes, phenyl With3-C6alkenyl,3-C6-quinil, phenyl-C3-C6alkenyl, oxetanyl, furyl or tetrahydrofuryl;

R85means hydrogen or C1-C4-alkyl;

R86means hydrogen, C1-C4-alkyl or C1-C4-alkylsulphonyl;

R87means hydrogen or C1-C4-alkyl; or

R86and R87together form4- or5-alkylenes group;

R88, R89, R90and R91independently of one another denote hydrogen or C1-C4-alkyl; or R88together with R89or R90together with R91independently on the angle from each other mean With 4- or5-alkylen, and the carbon atom may be replaced by oxygen, sulfur or one or two carbon atoms through-NR100-;

R92, R100and R93independently of one another denote hydrogen or C1-C6-alkyl;

or

R92and R93together mean With1-C6-alkylen;

R94means hydrogen or C1-C8-alkyl;

R97means hydrogen, C1-C6-alkyl, phenyl, phenyl-C1-C8-alkyl, and the phenyl ring may be substituted by fluorine, chlorine, bromine, nitro, cyano, -co3group1-C4-alkyl or CH3SO2group1-C4-alkoxy-C1-C8-alkyl, C3-C6alkenyl or3-C6-quinil;

R98means hydrogen With1-C8-alkyl, C3-C6alkenyl or3-C6-quinil, or R97and R98together mean With4- or5-alkylen, and the carbon atom may be replaced by oxygen or sulfur, or one or two carbon atoms may be replaced by-NR101;

R101means hydrogen or C1-C4-alkyl;

r is 0 or 1; and

s denotes 0, 1 or 2,

or the compound of formula (IIk)

R103means hydrogen, C1-C6-alkyl, C3-C 6-cycloalkyl,3-C6alkenyl or3-C6-quinil; and

R104, R105and R106independently of one another denote hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl or1-C6-alkoxy, provided that one of substituents R104, R105, R106different from hydrogen, and, in General, on 1 weight part of the active substance 2-(2-methoxycarbonyl-vinylsulfonylacetamido)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazole-3-one of formula (I) or its salt varies from 0.001 to 1000 parts by weight of one of the abovementioned compounds of group (b).

Defined by the General formula of the compounds of group (b) should be preferred over those that are listed in the following tables:

Table 1

The compounds of formula (IIa)

Conn. No.X1R32
1.01Cl-CH(CH3)-C5H11-n
1.02Cl-CH(CHC)-CH2OCH2CH=CH2
1.03ClH
1.04ClWith4H9-n

Table 2

The compounds of formula (IIb)

Conn. No.R38R39R40R41E
2.01CH3phenyl2-ClNSN
2.02CH3phenyl2-Cl4-ClSN
2.03CH3phenyl2-FNSN
2.04CH32-chlorophenyl2-FNSN
2.05With2H5CCl32-Cl4-ClN
2.06CH3phenyl2-Cl4-CF3N
2.07CH3phenyl2-Cl4-CF3N
2.08CH32-forfinal2-ClNSN

Table 3

The compounds of formula (IIc)

Conn. No.R29R30R31R27R28
3.01CH3CH3CH32-Cl4-Cl
3.02CH3With2H5CH32-Cl4-Cl
3.03CH3With2H5With2H52-Cl4-Cl
Table 4

The compounds of formula (IIe)

Conn. No.And2R14
4.001H
4.002H
4.003CH3
4.004 CH3
Table 5

The compounds of formula (IIf)

Conn. No.R56R57R56+R57
5.001CH2=SNSN2CH2=SNSN2-
5.002--
5.003--
5.004--
5.005--
5.006--
5.007 --
Table 6

The compounds of formula (IIg)

Conn. No.R80R79
6.01NCN
6.02ClCF3

Table 7

The compounds of formula (IIh)

Conn. No.R81
7.01N
7.02CH3
Table 8

The compounds of formula (IIm)

Conn. No.R82Z4Vr
8.001NO1
8.002N O1
8.003NO1
8.004NO1
8.005NCH21
8.006NCH21
8.007NS1
8.008NS1
8.009NNCH31
8.010NNCH31
8.011NNCH31
8.012N O1
8.013NS1

Table 9

The compounds of formula (IIn)

Conn. No.UR82Z4
9.001OH
9.002OH
9.003O5-Cl
9.004CH2H
9.005CH2H
9.006CH2H
9.007NH5-Cl
9.008NH5-Cl
9.009NHH
9.010NHH

Conn. No.UR82Z4
9.011NCH3H
9.012NCH3H
Table 10

The compounds of formula (II series)

Conn. No.UVrW1Z4R82
10.001OC=O1CH2H
10.002OC=O1CH2H
10.003 CH2C=O1CH2H
10.004CH2C=O1CH2H
10.005CH2CH21C=OH

Conn. No.UVrW1Z4R82
10.006CH2CH21C=OH
10.007NCH3C=O1CH2H
Table 11

The compounds of formula (IIp)

Conn.No. R82W1
11.0016-Cl
11.0026-Cl
11.003N
11.004N
11.005N

Table 12

The compounds of formula (IIk)

Conn. No.R103R104R105R106
12.01CH3NcyclopropylN
12.02CH3With2H5cyclopropylN
12.03CH3cyclopropylWith2H5N
12.04CH3CH3NN
12.05CH3CH3cyclopropylN
12.06CH3Och3Och3N
12.07CH3CH3Och3N
12.08CH3Och3CH3N
12.09CH3CH3CH3N
12.10With2H5CH3CH3N
12.11With2H5Och3Och3N
12.12NOch3Och3N
12.13NCH3CH3N
12.14With2H5NNCH3
12.15NNNCH3
12.16 CH3NNCH3

In accordance with the invention is particularly preferably a selective herbicide means that different content of the mixture of active substances, including

(a)2-(2-methoxycarbonyl-vinylsulfonylacetamido)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazole-3-one of formula (I)

and/or one or more salts of the compounds of formula (I), in particular the sodium salt,

(b) diethyl-1 -(2,4-dichlorophenyl)-4,5-dihydro-5-methyl - 1H-pyrazole-3,5-in primary forms (mefenpyr-diethyl), (1-etylhexyl)-[(5-chloro-8-quinolinyl)oxy]-acetate (cloquintocet-mexyl) and/or ethyl-1-(2,4-dichlorophenyl)-5-(tri-chloromethyl)-1H-1,2,4-triazole-3-carboxylate (Finlayson-ethyl), and, in General, on 1 weight part of the active substance 2-(2-methoxycarbonyl-vinylsulfonylacetamido)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazole-3-one of formula (I) is from 0.001 to 1000 parts by weight of one of the abovementioned compounds of group (b).

Obvious addition was found that herbicide active principle 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives can take the above protective function.

A preferred form of execution, hence, is also a mixture containing the compound of formula (I) and/or its salts, on the one hand, and 2,4-D is/or its derivatives, on the other hand. Typical derivatives of 2,4-D are, for example, esters.

Of the compounds of group (b), the most preferred is the compound diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-in primary forms (mefenpyr-diethyl).

Connection diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-in primary forms (mefenpyr-diethyl), (1-etylhexyl)-[(5-chloro-8-quinolinyl) oxy]-acetate (cloquintocet-mexyl) and ethyl-1-(2,4-dichlorophenyl)-5-(trichloromethyl)-N-1,2,4-triazole-3-carboxylate (Finlayson-ethyl) described in the following patents DE-A 39 395 03, EP- And 191 736 and accordingly DE-A 35 252 05. 2,4-D is unknown herbicide.

Among the salts of the compounds of formula (I) are preferred sodium, potassium, ammonium, methylammonium, ethylammonium, n - or ISO-propylammonium, n-, ISO-, sec - or tert-butylammonium, diethylammonium, diethylammonium, di-n-Propylamine, di-ISO-Propylamine, di-n-butylamine, di-ISO-butylamine, di-s-butylammonium, trimethylammonium, triethylammonium, Tripropylamine, tributylamine, trimethylsulfonium and triarylsulfonium salt.

Among the salts of the compounds of formula (II) or (III) is particularly preferred sodium, potassium, ammonium, methylammonium, ethylammonium, n - or ISO-propylammonium, dimethylammonium, diethylammonium, di-n-propylammonium, and-ISO-propylammonium and trimethylsulfonium salt, moreover, the predominant sodium salt.

Obvious it was found that videopreteen mixture of active compounds from 2-(2-methoxycarbonyl-vinylsulfonylacetamido)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazole-3-one of formula (I) and, respectively, salts and protective equipment/antidote from the above group (b) with very good compatibility with useful plants find especially high herbicide efficiency and can be used for selective weed control in various crops, in particular cereals, primarily wheat, and soybeans, potatoes, corn and rice.

As obvious, you should consider the fact that many well-known protective agents or antidotes which are capable of eliminating the harmful effects of herbicides on plants, just above compounds of group (b) can almost completely prevent the harmful effects on plants 2-(2-methoxycarbonylaminophenyl-aminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazole-3-one and its salts, in particular its sodium salt, with no impact on herbicide efficacy against weeds.

This ought to emphasize giving special advantages especially and most of all preferred mixture components from group (b), in particular from siteline save grain, as, for example, wheat, barley and rye, as cultivated plants.

In accordance with the invention, a mixture of active substances can be used, for example, for the following plants:

Dicotyledonous weed species: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convoivulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindemia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicotyledonous crops species: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Lirium, Ipomoca, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cuburbita, Helianthus.

Monocotyledonous weeds species: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cypenis, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristilis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecums, Apera.

Monocots culture species: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.

Application in accordance with the invention, mixtures of active substances in any case is not limited, however these species, and applies equally well to other plants.

Cultivated plants in accordance with the invention are thus all plants and varieties of plants, including transgenic plants and plant varieties.

Giving the benefit of the effect of tolerance of cultural plants of the inventive mixtures of active substances particularly pronounced in certain footnotereference. However, the weight ratio of the active substances in the mixture can vary within relatively wide limits. In General, on 1 weight part of the active substances of the formula (I) or its salt varies from 0.001 to 1000 weight parts, preferably from 0.01 to 100 weight parts and particularly preferably from 0.1 to 10 weight parts of one of the above (b) compounds that improve the resistance of cultivated plants (antidotes/protective equipment).

The active substance and, accordingly, mixtures of active substances can be translated in the usual preparative forms such as solutions, emulsions, powders for spraying, suspensions, powders, means for spraying, pastes, soluble powders, granules, concentrated suspensions-emulsions, impregnated active ingredient of natural and synthetic materials, as well as micro-capsules in polymeric materials.

These preparative forms are produced by known methods, for example by mixing the active substances with extenders, i.e. liquid solvents and/or solid carriers, if appropriate using surface-active agents, i.e. emulsifying or dispersing funds and/or blowing means.

In the case of use as a filler water as a accessory can also be used, for example, organic dissolved the Lee. In the case of liquid solvents to a significant extent we can talk about aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, such as oils, alcohols, such as butanol or glycol as well as their simple and esters, ketones such as acetone, methyl-ethyl-ketone, methyl-isobutyl-ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylsulphoxide and water.

As solid carriers can be considered, for example, ground natural rock, such as kaolin, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silicic acid, alumina and silicates. As solid carriers for granules are considered, for example, crushed and fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite, and also synthetic granules of inorganic and organic flour and granules of organic material such as sawdust, coconut shell, maize cobs and tobacco stems. As emulsifying and/or penoobrazuyuschaya means considered for example, non-ionic or anionic emulsifiers, such as complex polyoxyethylene ether fatty acids, simple polyoxyethylene ether of fatty alcohols, for example a simple alkilammonia broadcast polyglycol, alkyl sulphonates, alkyl sulphates, arylsulfonate, as well as protein hydrolysates. As the dispersing media is considered, for example lignin-sulphite lye and methylcellulose.

In the formulation can be applied adhesive substances such as carboxymethylcellulose, natural and synthetic powdered, granular or latex-molded polymers, such as gum Arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalin or lecithin and synthetic phospholipids. Other components can be mineral and vegetable oils.

Can be applied colorants such as inorganic pigments, for example iron oxide, titanium oxide, ferrocen blue, and organic dyestuffs, such as alizarin, azo and metallophthalocyanine dyes and micronutrients, such as iron salts, manganese, boron, copper, cobalt, molybdenum and zinc.

Preparative form in General contain the active substance, including preserving substances, in weight percent in the amount of from 0.1% to 95%, preferably from 0.5% to 90%.

The inventive mixture are active in the substances in General, applied in the form of finished compositions. However, contained in the mixtures of active substances can also be mixed in the application, i.e. to be used as mixtures in the tank.

New mixtures of active substances can be used both in themselves and in their formulation, to a significant extent, also in a mixture with other known herbicides, and, in turn, possible finished formulation or mixture in the vessel. It is also possible mixing with other known active substances, such as fungicides, insecticides, acaricides, nematicides, protective substances from birds, plant growth regulators, fertilizers, and tools that improve soil structure. For certain purposes, in particular in the way post-emergent, in the future can be advantageous to include in the preparative form as further additional materials portable plants, mineral or vegetable oils (for example, the commercial product "Oleo DuPont 11TH" ("Oleo®DuPont 11 E")) or ammonium salts such as ammonium sulphate or ammonium thiocyanate.

A mixture of active principles can be applied as such in the form of their formulations or in forms prepared from them by further dilution of applications, such as: ready-to-use solutions, suspensions, emulsions, powders, pastes and granulates. The use of Khujand is realized in the usual way, for example by watering, spraying, spraying, sprinkling or spreading.

Consumption of the inventive mixtures of active substances may vary within certain limits: it depends primarily on the weather and soil factors. In General, the quantity of material is in the range from 0.05 to 5 kg/ha, mainly from 0.05 to 2 kg/ha, especially preferably between 0.1 and 1.0 kg/ha

The inventive mixture of active substances can be applied before or after germination of the plants, i.e. the way to shoot or post-emergent.

Examples of the application

Were used the usual formulations of the prisoners in their active substances. When this self-made laboratory preparative form contained the sodium salt of the compounds of formula (I) as 70 WG 70 WP, mefenpyr-diethyl-as 100 the EU, as well as fenchlorphos-ethyl and cloquintocet-mexyl. Of active substances and, if necessary, the protective equipment was obtained aqueous solution for spraying with the addition of 0.1% ranexa-36 (Renex-36).

Example

Post-harvest test

Drug acting beginning sprayed with the test plants were grown in pots 10×10 cm (plant environment: land or vermiculate), so that a desired amount of current start was made on the unit square. The concentration of the solution for spraying was chosen so that in 500 l of water/ha was applied the desired amount of current to the beginning.

After about 18 days estimated the degree of damage to cultivated plants in % damage in comparison with the development of the untreated control plants.

Here means:

0% = no damage (as untreated control samples)

100% = total destruction/damage.

The active substance, account number, the test plants and the results are presented in the following tables, and are used in the tables names have the following meanings:

Wheat = wheat varieties Orestis

Barley = barley varieties Coronar

AV = active substance/protectant

sodium salt of compound (I) =

Table A1

Post-harvest test/greenhouse
Active(s) substance(a)Consumption (g AV/ ha)Damage

wheat [in%]
Sodium salt compounds

formula (I)
18030
9020
Sodium salt compounds

formula (I)

+

Finlayson-ethyl
180+50010
90+50010
180+4510
90+4510

Table A2

Post-harvest test/greenhouse
Active(s) substance(a)Consumption (g AV/ ha)Damage

wheat [in%]
Sodium salt compounds

formula (I)
25050
12530
6020
Sodium salt compounds

formula (I)

+

mefenpyr-diethyl -
250+25020
125+1250
60+600
Table A3

Post-harvest test/greenhouse
Active(s) substance(a)Consumption (g AV/ ha)Damage

wheat [in%]
Sodium salt compounds

formula (I)
12550
6010
305
Sodium salt compounds

formula (I)

+

mefenpyr-diethyl -
125+12510
60+605
30+300
Table A4

Post-harvest test/greenhouse
Active(s) substance(a)Consumption (g AV/ ha)is avridine

wheat [in%]
Sodium salt compounds

formula (I)
12540
6030
Sodium salt compounds

formula (I)

+

mefenpyr-diethyl -
125+25010
60+2500

Table A5

Post-harvest test/greenhouse
Active(s) substance(a)Consumption (g AV/ ha)Damage

barley [in%]
Sodium salt compounds

formula (I)
6070
3070
1550
Sodium salt compounds

formula (I)

+

mefenpyr-diethyl -
60+6060
30+3050
15+1530

Table A6

Post-harvest test/greenhouse
Active(s) substance(a)Consumption (g AV/ ha)Damage

barley [in%]
Sodium salt compounds

formula (I)
6060
30 60
1550
850
Sodium salt compounds

formula (I)

+

mefenpyr-diethyl -
60+20050
30+20030
15+20030
8+2005
60+5060
30+5040
15+5030
8+5010

Table A7

Post-harvest test/greenhouse
Active(s) substance(a)Consumption (g AV/ ha)Damage to wheat [in %]
The sodium salt of the compounds of formula (I)25050
12530
6020
The sodium salt of the compounds of formula (I) + cloquintocet-mexyl250+25020
125+12510
60+600
Table A8

Post-harvest test/greenhouse
Active(s) substance(a)Consumption (g AV/ ha)Damage to wheat [in %]
The sodium salt of the compounds of formula (I)12550
6010
305
The sodium salt of the compounds of formula (I) + cloquintocet-mexyl125+12510
60+605
30+300
Table A9

Post-harvest test/greenhouse
Active(s) substance(a)Consumption (g AV/ ha)Damage to the barley [in %]
The sodium salt of the compounds of formula (I)6070
3070
1550
The sodium salt of the compounds of formula (I)

+

cloquintocet-mexyl
60+6060
30+3050
15+1530

Example B

Repeat the experience on the example And with the only difference that the concentration of the solution for spraying chose to 300 l of water/ha was applied the desired amount of current to the beginning, and that the degree of damage to cultivated plants were evaluated after 21 days. In addition, in tables B1 to B3 is additionally given the degree of reduction of damage to cultivated plants in % when you share a connection that improves the resistance of cultivated plants, compared with using only herbicide.

40
Table B1
PlantsHerbicideConsumption (g AV/ha)The antidoteConsumption (g AV/ha)Damage%The degree of reduction in%
Wheat (cultivar. Triso)Flucarbazone480--50-
Flucarbazone480mefenpyr-diethyl - 4510
Connection 1480--50-
Connection 1480mefenpyr-diethyl - 400100
Table B2
PlantsHerbicideConsumption (g AV/ha)The antidoteConsumption (g AV/ha)Damage

in%
The degree of reduction

in%
Barley (variety: Baroness)Flucarbazone -

sodium salt
480--43-
Flucarbazone -

sodium salt
480mefenpyr-diethyl - 1203030
Compound I -

sodium salt
480--40-
Compound I -

sodium salt
480mefenpyr-diethyl - 1200100
Table B3
PlantsHerbicideConsumption (g AV/ha)The antidoteConsumption (g AV/ha)Damage%The degree of reduction

in%
Barley (cultivar. Skarlett)Flucarbazone -

sodium salt
120--33-
Flucarbazone -

sodium salt
120mefenpyr-diethyl - 120300
Compound I -

sodium salt
120--35 -
Compound I -

sodium salt
120mefenpyr-diethyl - 1201071

Herbicide agent, containing an effective amount of a mixture of active substances, including

(a) 2-(2-methoxycarbonyl-vinylsulfonylacetamido)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazole-3-one of formula (I)

or its sodium salt,

(b) the connection improves the resistance of cultivated plants, representing diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-in primary forms (mefenpyr-diethyl), and 1 parts of active substance (a) is from 0.025 to 25 parts of the compound (b).



 

Same patents:

Herbicidal agent // 2260948

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to herbicidal agent containing 2,6-disubstituted pyridine derivative of general formula I wherein R1 is phenyl radical monosubstituted with halogen; R2 is phenoxy radical monosubstituted with C1-C3-haloalkyl, as well as herbicidal compound selected from group comprising N-isopropyl-N-(4-fluorophenyl)-amide of (5-trifluoromethyl-1,3,4-thiadiazole-2-yl-oxy)-acetic acid (fluphenacete), 2-(2-methoxycarbonyl-phenylsulfonylaminocarbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-1,2,4-triazole-3-one (propoxycarbazone) and sodium propoxycarbazone wherein weight ratio of pyridine derivative to compound from said group is 1:0.5-15.

EFFECT: effective agent useful in selective controlling of weeds, in particular in grain crops.

5 cl, 17 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, plant science.

SUBSTANCE: it is suggested a herbicide preparation for selective weed control in cereals containing 2-(2-trifluoromethoxyphenylsulfonylaminocarbonyl)-4-methyl-5-methoxy-2.4-dihydro-3H-1,2,4-triazole-3-on or its salt in efficient quantity and method for selective weed control. The innovation provides efficient weed suppression in cereals, wheat, in particular.

EFFECT: higher efficiency.

6 cl, 4 ex, 6 tbl

The invention relates to agriculture and veterinary medicine

FIELD: organic chemistry, agriculture, insecticides.

SUBSTANCE: invention relates to a substituted anilide derivative of the formula (I): wherein R1 represents hydrogen atom, (C1-C6)-alkyl group; R2 represents hydrogen atom, halogen atom or halogen-(C1-C6)-alkyl group; R3 represents hydrogen atom, halogen atom, (C1-C6)-alkyl group, hydroxyl group or (C1-C6)-alkoxy-group; t = 1; m = 0; each among X that can be similar or different represents (C2-C8)-alkyl group, hydroxy-(C1-C6)-alkyl group or (C3-C6)-cycloalkyl-(C1-C6)-alkyl group; n = 1 or 2; Z represents oxygen atom; Q means a substitute represented by any of the following formulae: Q1-Q3, Q6, Q8-Q12, Q14-Q19, Q21 and Q23 (wherein each among Y1 that can be similar or different represents halogen atom, (C1-C6)-alkyl group, and so on); Y2 represents (C1-C6)-alkyl group or halogen-(C1-C6)-alkyl group; Y3 represents (C1-C6)-alkyl group, halogen-(C1-C6)-alkyl group or substituted phenyl group; p represents a whole number from 1 to 2; q represents a whole number from 0 or 2; r represents a whole number from 0 to 2. Also, invention proposes a chemical for control of pests of agricultural and fruit crops. The chemical comprises substituted anilide derivative of the formula (I) as an active component and represents insecticide, fungicide or acaricide. Also, invention proposes a method for addition of the chemical for control of pests of agricultural and fruits crops. Also, invention proposes aniline derivative represented by the general formula (II): wherein R1 represents hydrogen atom, (C1-C6)-alkyl group; R2 represents hydrogen atom, halogen atom or halogen-(C1-C6)-alkyl group; R3 represents hydrogen atom, halogen atom, (C1-C6)-alkyl group, hydroxyl group or (C1-C6)-alkoxy-group; t = 1; m = 0; each among X that can be similar or different represents (C2-C8)-alkyl group, hydroxy-(C1-C6)-alkyl group or (C3-C6)-cycloalkyl-(C1-C6)-alkyl group; n = 1 or 2. Invention provides the development of anilide derivative as insecticide, fungicide and acaricide against pests of agricultural and fruit crops.

EFFECT: valuable properties of compound.

5 cl, 6 tbl, 27 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention describes derivative of 1-aryl-3-cyano-5-pyridylalkylaminopyrazole represented by the following formula (1): wherein X represents C-halogen; R1 represents halogenalkyl group comprising from 1 to 4 carbon atoms with exception of perhalogenalkyl group; R2 represents hydrogen atom; R3 represents hydrogen atom; R4 represents hydrogen atom. Also, invention describes an agent used for control of insects comprising this derivative as an active component. Invention describes two methods for preparing compound of the formula 91). Compounds of the formula (1) are useful for control of insects in agriculture and for domestic animals.

EFFECT: improved preparing methods, valuable properties of compound and agent.

7 cl, 7 tbl, 7 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:

wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention describes insecticide composition comprising the active amount of one pyridine compound of the formula (I)

or its salt wherein Y represents halogenalkyl group comprising from 1 to 2 carbon atoms and halogen atoms from 1 to 5; m = 0; Q represents compound of the formula:

wherein X represents oxygen atom; R1 and R2 represent independently hydrogen atom, alkyl group comprising from 1 to 6 carbon atoms and substituted with cyan-group, and one insecticide taken among carbofuran, carbosulfan, cipermethrin, bifentrin, acetamiprid, chlorfauazuron, fluphenoxuron, piriproxiphen, spinosad, emamectine benzoate, avermectin, buprophezin and fipronil taken in the weight ratio of compound of the formula (I) and other insecticide = from 1:2 to 100:1. The composition provides stable and strong effect and eradicates insects.

EFFECT: strong insecticide effect of composition.

4 cl, 11 tbl, 5 ex

FIELD: agriculture, in particular method for controlling of specific insect pests.

SUBSTANCE: invention relates to method for controlling of lepidopterous, homopterous, hemipterans, coleopterous, and physopods by contacting of said pests or environment thereof with effective amount of compound of formula I SSS1, N-oxide or agriculturally acceptable salt thereof being effective against abovementioned insects, wherein A and B are independently O or S; R1, R2 represent H, C1-C6-alkyl; R3 represents H, optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or C3-C6-cycloalkyl; R4 represents H, C1-C6-alkyl, C2-C6-alkinyl, C1-C6-haloalkyl, CN, halogen, C1-C4-alkoxy, C1-C4-haloalkoxy, NO2;. R5 represents H, C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-hydroxyalkyl, CO2R11R12, halogen or C1-C4-alkoxy; R6 represents H, C1-C6-alkyl, C1-C6-haloalkyl; R7 represents H, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, phenyl ring, benzyl ring, or 5-6-membered heteroaromatic rind, naphthyl ring system, or 8-10-membered condensed heterodicyclic system. Also claimed are compound of formula I and benzoxazine derivative of formula 10 .

EFFECT: compounds effective against agriculture spineless depredators.

22 cl, 13 tbl, 1 dwg, 24 ex

FIELD: organic chemistry, fungicides, agriculture.

SUBSTANCE: invention describes pyrazolcarboxamide of the formula (I) wherein if X means oxygen atom (O) then R1 represents (C1-C3)-alkoxy-(C1-C3)-alkyl; R2 means (C1-C3)-halogenalkyl; R3 means fluorine (F), chlorine (Cl) or bromine atom (Br), and if X means sulfur atom (S) then R1 means (C1-C3)-alkyl; R2 means (C1-C3)-halogenalkyl; R3 means halogen atom. Also, invention describes a method for preparing compounds of the formula (I), a composition for control of microorganisms and prevention for their attack and damage of plants, and a method for control of phytopathogen organisms, and compound of the formula (V) wherein X means sulfur atom (S); R1 means (C1-C3)-alkyl; R2 means (C1-C3)-halogenalkyl; R3 means chlorine, bromide or iodine atom. Invention provides control and prevention in infection of plants with phytopathogenic microorganisms - fungi in agriculture and horticulture.

EFFECT: valuable agricultural properties of compounds.

9 cl, 4 tbl, 12 ex

FIELD: organic chemistry, insecticides, chemical technology.

SUBSTANCE: invention describes derivative of 1-aryl-3-cyano-5-heteroarylalkylaminopyrazole of the general formula (1): wherein A means: (A-1) , (A-2) , (A-3) and (A-4) and wherein X represents C-halogen; R1 represents (C1-C4)-alkyl group or halogen-(C1-C4)-alkyl group; A represents any group among (A-1) - (A-4) wherein R4 represents hydrogen atom or (C1-C4)-alkyl group; n = 0, 1 or 2 under condition that R1 represents halogen-(C1-C4)-alkyl group with exception for perhalogenalkyl group when A represents (A-1) and n = 0, and that n doesn't equal 0 when A represents (A-4). Also, invention describes derivative of pyrazole of the formula (2): wherein A means: (A-1) and Y means: (Y-1) , (Y-2) and (Y-3) wherein X, R2, R3 and R4 have values given above; R5 represents hydrogen atom; A represents (A-1); Y means any group among (Y-1) - (Y-3); Z represents halogen atom that are intermediate compounds used for synthesis of the compound (1). Invention describes methods for preparing compounds of the formula (1) and (2) and insecticide comprising compound of the formula (1) as an active component. Insecticide shows high systemic activity, high safety and reduced harmful effect on environment in vicinity areas of its applying.

EFFECT: improved methods for preparing, valuable insecticide properties of compound.

11 cl, 9 tbl, 19 ex

FIELD: organic chemistry, agriculture, fungicide compositions.

SUBSTANCE: invention relates to compounds of formula I

, wherein R1 and R2 are hydrogen or C1-C4-alkyl; X is C3-C8-cycloalkyl, phenyl or styryl, as well as method for production thereof and fungicide composition containing the same. Compounds of present invention have fungicide activity and are useful in effective controlling of deleterious fungi.

EFFECT: compounds and fungicide composition with improved effectiveness.

3 cl, 2 tbl, 4 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, agriculture.

SUBSTANCE: invention describes a new compound 4,6-bis-(morpholyl)-2-[(2'-ethoxyacetyltetrazolyl)-5'-yl]-1,3,5-triazine of the formula: that represents an antidote against phytotoxic effect of herbicide 2,4-dichlorophenoxyacetic acid on germinating sunflower seeds and seedlings.

EFFECT: valuable properties of compound.

2 cl, 2 tbl, 3 ex

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