DE1667976A1 - Herbicidal composition and process for its preparation - Google Patents

Description

Herbicidal ztisazamensetziuig and process for their preparation

PISOIJS PEST CORNTROL LIMITED Harston / Cambridgeshire United Kingdom

The present invention relates to new ones Sfcoffeusasn & eneeb & ungen, especially for the selective © Suitable for weed control and

It has been found that the following Operated eelective herbicidal compounds an exceptional activity in selective control of certain weed species in different crops.

Accordingly, the present invention relates to a selective herbicidal composition consisting of

one

BATH

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a meofanng an # e Xriaeins of the general formula

fs

/ ⁰ V

"I H B

N II I
»- ο σ -

where R »Β ² · Ir and BT are hydrogen, alkyl» for example with 1 Ma 6 carbon atoms (such as methyl, ethyl and isopropyl) or alkoxy alkyl, in which, for example, the altyl has 1 to 6 carbon atoms (such as mefehoxypropyl) mean _y with at least a substituted bensimidazole of the formula

B ⁶

0 -H

wherein Ir is hydrogen »a lower alkyl group (for example, with 1-4 carbon atoms, such as methyl or ethyl) or -COOR ¹⁰ , where S ^{10 is} alkyl (for example with 1 - β carbon atoms, such as methyl» ithyl or propyl) »substituted alkyl (for example Chloromethyl or bromine

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Sthyl), aryl (for example phenyl or kaphthyl) or substituted aryl (such as aralkyl, for example ToIy 1 or Xärlyl) or eykloalkyl (for example cyclopentyl or cyclohexyl) denotes 1 and R ⁶ , R ⁷ , R ⁸ and H ^{9 are the} same or different bind and hydrogen, alkyl (for example with 1-6 carbon atoms * such as methyl, xthyl or propyl), hydroxy, alkoxy (for example methoxy, ethoxy or butoxy), nitro ι halogen (for example chlorine, bromine or fluorine), pseudohalogen (e.g. cyan , Thiooyan, isothiocyan or aiido), substituted alkyl (beleplelewelee trifluoromethyl, chloromethyl, bromomethyl, trichlonaethyl, hydroxymefchyl, 2-chloroethyl, 2- ^ rdroayethyl or 2-methosylethyl), carboxy, oxy-substituted or di-substituted carboxyamide amino or mono- or dieubstituiertöß amino (for example, methyl amines "Dime * hy 1-amino, acetylamino, trifluoroacetylamino) _f thiol, alkylthiol or oxidized derivatives thereof (belspleleweise -SOR 'ode r SOgR?, where R AUyI means), sulfonic acid and Eefeer and amide hieron, or a heterocyclic ring "which is bound to the benzene sol system by a tick off from om" means "and X represents trifluoromethyl or pentafluoroethyl" or a salt or functional parts Derivative of this benzimidazole, if such * exists »

Certain of the above mentioned triasins bind as Known herbicides! for example selenium mentions 2-methylthio-

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4 ~ isopropylaiaino-6- (j ^ -methoxypropyl) -amino-1 _S 3 _? 5-fcriazine ₅ 2 _l 4-bit- (MoBofithylamino) -6-methylmercapfcoHB-triaein (Simetryn)

(Desmetryn) »2 _# #
(Prometryn) and 2-e-feriaain (Ametryn) *

According to a preliminary embodiment of the fiadang, the triazine has the above formula, in which at least one of the groups R, R ² , Έ? tmd R is an alkyl group, eB y-mefchoxypropyl, denotedefc. According to a particularly preferred embodiment, the triazine is 2-Mefclcrlt; hio-4-leopropylbino-6- ( £ - * ethO3 ^ propyl) -amino-

The above-mentioned substituted benzimidazoles are active herbicides and were, for example, in Patent f 42011 ivd / i2p

honored. Example · of these substituted benzimidazoles are:

♦ »5» 6 »7-3P * traohlor-2-trifluor» e thgrlbenzimidazol ₉ 4.5

4.5 _t 7-0? RiohlO2> -2-brifluorffiethylbenzlmida2ol, 4 _t 5-dichloro-2-trifluoromethylbenzimidazole, 5-iodo-2 «-trifluorme tbylbenzimidazole»
5-0! Sreno-2-trifluoromethylbenziaidazole,

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4, 7-dichloro-2-trifluoirae thylbenaimidaeol, 5 ^ hlor-2-trifluormefchylbenaimidaaol,

4-GhXor «6 ~ nitro-2-trifXuoxmethyXbenBiioidazoX,

4,6 ₃ 7-Trichloiv5 ^ ne bhyl-2-

4,5,6-0? Riclilor-2-peftkafltioräfchylbenzimidaaol,

Morpholinfcriclilop-a-fcrlfluormefehylbeniimidazole, 1 ^ arboSthoay ^ _t 5 »6-t; richlo2> -2-brifliiormefchylbe2izilmidazole and

According to a preferred embodiment of the dung is the substituted benaimidazole 5-iodo-2-ferifluoro-

or 4,5-Diohlor-2-triflttormet; hylb «n3-

imidazole. According to a further proposed embodiment of the present invention, it consists of a mixture of 5-0Od-2-fcrifluoromefchylbeneimidaol or 4,5-dichloro-2-ferifluoromethylbenzimidaol and
amino-6- (^ Ηΐιβ * 1ι «« 3τρΓορ3ΓΧ)

It was found that the mixtures according to the invention have a herbicidal activity which is considerably higher than the herbicidal activity of the ingredients of the mixture f the mixtures accordingly exhibit synergisms.

They are salts of the substituted benzimidazoles

water proceedsXieh

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water soluble, and therefore can when applied; will" as aqueous solutions »appropriately in connection with a wetting agent. The water-insoluble substituted benzimidazoles can be used in any of the ways customary for insoluble compounds together with wetting agents, Solvents, solid thinners new. formulated will.

The triazines are very slightly soluble in all liquids and must therefore as a suspension can be formulated _for example as aqueous suspension · The herbicidal mixture can therefore be, for example, an aqueous suspension of both the benzimidazoles and the triazines. On the other hand, a physically stable formulation is a wettable powder formulation of a mixture of the finely ground triazines, an inert diluent and a solid salt, for example the sodium al ζ of the substituted benzimidazole.

The proportions of triazines and substituted benzimidazoles in a composition can vary widely and are, for example, about 1-50 parts of triazine mixed with about 1-100 parts of the substituted benzimidazole, Conveniently, the composition contains 0.25 - 75 Parts of the substituted benzimidazole to one part triazine and, according to a preferred embodiment, about 2 to 4

Tail »

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Parts of the substituted benzimidazole to 1 part of triazine.

The present invention also relates to a method for the selective control of weeds in crops » the application behavior can never be strong depending on the genus of fruit vary and is generally on the order of about 140 grams - 2.24 kg per hectare of active ingredients.

So it is preferable to choose the composition so that 20-560 g per hectare of triasin and 140 g to 1.12 kg of substituted benzimidazole are used on the crops

The compositions of the invention can also contain one or more other selective herbicides and it has been found that in some cases it is advantageous to add a substituted phenoxyaliphatic acid to the composition. In such mixtures, the substituted phenosyaliphatic acid can be an alkyl and / or halogen substituted phenosyaliphatic acid and their salts, for example alkali metal, amine and alkanolamine salts, and functional derivatives, for example esters and amides. These compounds may have such an activity as to be regarded as commercially available herbicides, or they may have little herbicidal activity. Examples of substituted phenosyaliphatic acids are: 2,4-dichlorophenoxy acetic acid, 2-methyl-4-chlorophenoxyacetic acid, 2,4,5-tricbJLorpheno3C3reaeigaaure ₉ £ ~ 2 ~ 4-dichlorophenoxy ~ butyric acid, y-2 ~ mefchyl-4-chlorophenoxybutyric acid and _i * _2-Vethyl-4-chlorophenoxypropioic acid · These preliminary compounds are preferably used in the form of a salt.

The 109831/2004

The amount of substituted phenoxyaliphatic acid in the mixture is expediently 0.5 to ₉ parts, preferably 1 to 2 parts per part of substituted benzimidazoles.

The compositions of the invention may contain any common "commonly used" ingredient such as surfactants, adhesives, diluents, and other additives. The composition may contain liquids ₉ suitable for spraying "or fulver _y suitable for atomization. The degree of dilution by spraying does not seem to be critical"

The active constituents can be parglized or dissolved in the carrier in any suitable manner for use.

For example, the active ingredients can be dissolved in a water-immiscible solvent _f such as a hydrocarbon with a high boiling point that usually contains dissolved emulsifiers in order to be effective as a self-emulsifiable oil when added to water.

The active ingredients can also be mixed with a wetting agent with or without an inert diluent to a wettable Powders are mixed which is soluble or dispersible in water, or they can be mixed with the inert diluent to form a solid or powdered product be mixed.

• ·

Inert 109831/2004

Inert diluents containing the active ingredient are solid inert media including powdered or divided solid materials, For example clays "sand, talc, mica, fertilizers, etc." whereby these products have a particle size "that is dusty or is greater

The wetting agents used can be anionic compounds be * such as »soaps, fat sulfate esters, such as dodecyl sodium sulfate, octadecyl sodium sulfate and Ce ty! Sodium sulphate, fatty aromatic sulphonates such as alkyl benzene sulphonates or Ba tylnaphthalineulfonat, more complex fatty sulfonates, like the amide condensation product of oleic acid and N-methyltaurine or the sodium sulfonate of dioctylsuooinate

The wetting agents can also be non-ionic wetting agents be, for example the condensation products of fatty acids, Fatty alcohols or fat-substituted phenols with Ethylene oxide, or fatty acid esters and ethers of sugars or polyhydric alcohols or the products obtained from the latter by condensation with ethylene oxide or those as Bloek copolymers products known from ethylene oxide and propylene oxide The wetting agents can also be cationic agents, for example cetyltrimethylammonium bromide and the like.

. The erfindungegem & Ben compositions are at particularly valuable in combating weeds in grain,

jiniparticularly

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in particular for post-processing of crops · types of grain that can be protected in this way Ways «equipment, corn«, oats, rice and sugar cane.

When using these mixtures, the degree of destruction of the weed species is decidedly greater than τοη of the herbisiden Effect of the one part would be expected

The following examples are presented to the present invention explain in more detail without, however, being restricted to this * The parts are based on weight.

A mixture of 2 parts of 5-iodo-2-trifluoromethylbenimidazole (Compound I) and 1 part of 2-methylthio-4-iso ~ propylamino-6- (Jf-methoxypropyl) -amino-1,3 »5-triazine (compound II) as an aqueous suspension of a wettable powder was on various junp weed species in a ratio of 630 grams per hectare of the two combined ingredients sprayed. At intervals of 4, 6 and 8 days after spraying was the degree of plant destruction on the basis of a Scale from 0 to 100 by comparison with non-sprayed control plants For comparison purposes, the compound I in a ratio of 840 g per hectare and the compound II in a ratio of 420 g per hectare each alone sprayed.

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The table below shows the extent of herbicidal activity Effect on chickweed, dog chamomile, speedwell and Sticky herb caused by the respective composition at intervals of 4 »6 and 3 days after spraying became·

Days Chickweed
4 6 8 Dog chamomile
4 6 8 Honorary award
4 6 8 Elebkraut
4 6 8 Compound I.
840 g / ha 7 12 24 0 0 4 111 6 8 14 Compound II
420 g / ha 1 3 24 2 22 30 2 24 32 0 0 0 Compound I.
420 g / ha ♦ 45 62 69 29 61 7 * 14 35 42 11 14 17 210 g / ha

EXAMPLE· 2%

A Iflechung of 4 parts of 5 iodo-2-trifluoromethyl luormethylbensimidasol and 1 part of 2 ^ ethylthio-4-ieopropylamino -6- ⁱ '(y-methoxypropyl) amino-1 _t 3,5-triazine as an aqueous suspension of a net "cash Powder produced and planted in a ratio of 700 g / ha on various young weeds, as described in Example 1, sprayed. The degree of destruction of the plants, expressed in% weed killing * was measured 2, 4, 7 and 17 days after spraying and the results obtained are given below

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Days after
spray 2 92 7th 17th Weed arrows: 53 Yogelmlere 30th 73 9 * 100 Honorary award 27 92 97 97 Sticky herb 57 77 97 Dog chamomile 100 100

EXAMPLE 3t

The following compositions were found to be aqueous Suspensions made of wettable powders:

A. 4,5-dichloro-2-trifluoromethylbene imidazole 6 parts

2-methylthio-4-isopropylamino-6- (^ me thosypropyl) amino-1,3,5-fcriazine

2-Mefchyl - ^ - ohlorphenoxyeBeigsäure

B. 5-iodo-2-trifluoromethylbenzimidazo!

2-methylthio-4-ieopropylamino-6 - (^ methoxypropyl) -amino-1 ₉ 5 # 5'triazine

12 6

2 12

dd

2-Methy 1-4-phenoxy acetic acid

Alone a comparison was also made in the following Compositions made with an active ingredient component:

C. 2-4lethyl-4-chloropheno ^ acetic acid

D. 2-methylthio-4-ieopropylla-amino «-6- ( • / - -methoxypropyl) -amino-1,3,5-triasin.

• These concoctions were made on wheat and barley ·

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fields »infected with different species of weeds? were sprayed when the ivy plants were in the 2 - 3-Blafefc stage * The application ratio, based on the combined active constituent parts, was as follows:
At 140 g / ha
Bi W g / ha
C «140 g / ha
D: 14 g / ha

The degree of weed killing, expressed as% of the untreated Eon troll plants, was as follows x

composition X B. C. D. Weed species black bindweed (P.convolvulus) 92 87 60 28 P.persicaria 100 97 30th 7th Chickweed (6. media) 99 97 38 44 Knotweed (P aviculare) 88 90 60 25th Field Honor Award (V. agrestie) 8th? 80 35 10 Gefcreidedobterblume (C.eegetum) 79 52 36 30th

In the previous examples, the substituted benzimidazole and the phenoxyaliphatic acid were used used in the form of the sodium salts; according to the usual In practice, the weights are based on the acid equivalent.

The treatment of weed infected people

money fruits a

BATH ORIGINAL

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Field crops according to the present invention are moderately undertaken when the field crop; in the 2 to 5 ~ BlafctHSfcaditfm ₉ preferably in the 2 to 3 ^M Blafefcsfeadium-

109831/2004 bad original

Claims (1)

Claims 1 »Herbicidal composition, characterized., that they are a mixture of a triasin of general formula NS, Il I Γ- C 0-3 wherein H ₅ R , Έτ and R are hydrogen, alkyl or alkoxyalkyl groups and at least one substituted BQHzimidazole of the general formula R ⁶ I. B? -C ^ ^ C c I, j B ⁵ 9 109831/2004 in which Ir Wassere feoff _s denotes a lower alkyl group or ~ COOR; where R is alkyl $ substituted alkyl »aryl _s subfcuierfces aryl or cycloalkyl, and where R ₉ E ', R ⁸ and r9 are identical or different and water feoff _β alkyl ι Hydrosys- alkoxy, nitro, halogen, fseudohalogen, substituted alkyl, carboxy ₉ carboxy es tier ₉ carboxyamide _s N-subsfcibuierfces carbosyamid »H-disubsfcifeuierbes carbosyamidj Amino, monosubsfcifeuierfcee amino, disubsfeifeuieriyes or oxygen-containing amino, thiol, alkylfchiol and oxidizing acid, esters and amides thereof or a ring that is systamically bonded to the benzimidazole by a nitrogen atom and T 3 is rifluoromefchyl or pentafluoroethyl, or a salt or functional group Derivative of this benzimidazole, if there are any? consists" 2 · Herbicidal composition according to claim 1 »thereby characterized in that the ratio of the triazines to the substituted Benzimidazole in the range of 1-50! Parts of the the former is 1 - 100 parts of the latter. 5 · Herbicidal composition according to claim 2 «thereby characterizedο that the ratio of the triazine to the substituted benzimidazole is about 1 part of triazine to 2-4 parts of the substituted benzimidazole. BATH 109831/2004 4j Herbicidal composition according to one or more of the preceding claims, characterized in that the triazine 2 ^ ethylthio ^ -isopropylamino-6 - (; f «metho: ^ y <~ propyl) -amino-1,3 ₉ 5 ~ tii ^k iazia ₉ 2 ₅ 4 ~ bie-Isopropylamino ~ 6 ~ methylthio-s ~ triazine ₉ 2-1 thylamino «4-isopropylamino ~ 6-ethyl thio-> s ~ triazine» 2 »4-bis (monoethylamino)« 6-methylmercapfco * s-fcriazine or 2-Ieopropylaraino-4-mefehylamino-6-methylmercapiso-ß-triazine is " 5. Herbicidal composition according to one or more of the preceding claims, characterized in that in the triazine used, at least one of the groups R ₉ R ² _P H ⁵ and R ⁴ alkosyalkyl. 6. Herbicidal composition according to claim 5 »thereby marked »that in the triazine used at least one Λ p X Λ of the groups R, R, R ^ and R y * MethO3? yp2? opiy3 · is · 7 »Herbicidal composition according to one or more of the preceding claims »characterized» that the iPriazift 2-Mefchyltehio-4-isopropylamino-6 ~ (v "-metihoxy" - propyl) -amino-1 »3,5-triazine is 8. Herbiside composition according to one or more of the preceding claims »characterized in that the substituted benzimidazole 4,5,6,7-tetrachlor ~ 2 ~ t; j» i ~ fluoromethylbtnÄimidazole, 4 ₉ 5 ₉ 6-trichloro-2-tri £ luoromethyl benzimidazole, 109831 / 2D04 bad "benzjmidazol _{t 4.5}} 7 * iPrichl02 - '2-fcrifluormebhylbenzimidazo ?. 4.5" Diohlor-2-trifluoromethylbenzimidazole _s 5 ~ iodine-2-brifluorme fchylbenzimidaaol, 5-Qyan ~ 2-fcrifliaoime thylbenaimidazol _s 4 _ä 6- Dichloro-2-t; rifluoriaet; hylbenzimidazol »4,7-dichloro-2-trifluoxmetbylbeneimidazole _} 4-®it? Ro-6-chloro-2-'brif luoiane febylbenzimidazol» 4-CbJ.or-6 «-iiifero-2 ™ fcrif luorme methylbenzimidazole ₇ 4-chloro-2-brofluoroethylbenzimidazole »4-bromo" 5 ₉ 6 _s 7-i; riöhloa? - 2-brlfluoromebhylbenzimidazole * 4 »6,7-SE'iehlor-5- * metrhyl ~ 2 ~ ferlfluoromebhylbenadmidazole , 4,5 »6-5 & * JLchlor-" 2-penfcafluoräfehylbenaimidasol _t 5-ΪΤ1 fcro-2 ~ penfcafluoräbhylbenaimidasol, Morpholinouriohlor-S-trifluoraebbylbenziinidasol _} 1-Carbo · äbho3y «4 95 _t 6-2-i * ich : rif luormebhylbenizimidaaol or * »5> 6» 7 * -TebrachlO2 »-1-mefchyl-2 ~ ferifluorme fehylbenzimidazole 1st. 9 · Herbicidal composition according to, one or more of the preceding claims »characterized ₅ that the subsbibuated beeneimidazole is 5-iodo-2-brifluonnebh5rlbeni; -imidazole or ^^ - dichloro-S-brifluoromebhylbenzimidazole" 10 · Herbicidal composition according to one or more of the preceding claims _t characterized; * That eie a Uieohung of 2-4iebhylbhio-4-isopropylamino - & - (y-mebhoxypropyl) amino-1,3i5-triazine, and 5-iodo "2-fcrif luorme bhylbenzimidasol or _4-f 5 Diehlor ~ 2 ~ bri £ Contains luorme methylbenzimidazole. 11 109831/2004 bad original 11. Herbicidal composition according to claim 10, characterized characterized »that they are a mixture of 2-methylthio-4-isopropylamine-6- ( f Methoxypropyl) ~ amiiio ~ 1, J5,5 ~ tria 'ln and 5-iodo-2-trifluoromethyl "benzimida" ol In a ratio from about 1 part of the former to 2 - # parts of the latter contains ;. 12 «Herbicide · Composition according to one or more of the preceding claims »characterized in that the substituted benzimidazole is present in the form of a salt» 13 · Herbicidal composition according to one or more of the preceding claims »characterized in that They use a surface active substance and / or an adhesive and / or a 7dünnungßmit? t? dl ent? 14 · Herbicides ZoBammeneetBUSg m «9h« in # m or more of the preceding claims »characterized in that it contains another selective herbicide. 15 · Herbicidal composition according to one or more of the preceding claims * characterized in that it is also a substituted phenoxyaliphatic acid or contains a salt or a fractional derivative thereof » 16. Herbicidal composition according to claim 15, characterized marked that the substituted phenosylaliphatic Acid 2-! Totl7l-4-chlorophenoxyacetic acid or <x-2-methyl-4 * chlorophenoj7proplonic acid 1st. 10983W2004 ΛΟ "17 · herbicidal composition according to claim 15 or 16 characterized in which the _S substituted phenoxyali" phatisohe file acid in an amount of 0.5-4 per part dee substituted benzimidazoles present · 18 «A method for producing einar herbicidal composition roof one or more of claims 1 to 17 ·" _s characterized in that a triazine and a substituted benzimidazoles as described above, are mixed " 19 · Weed control method characterized in that on the fertile oak or the Soil a mixture of a triazine and a substituted one Benzimidazoles as described above are used BATH 109831/2004 ^BAÜ