CA2053715A1 - Synergistic herbicidal compositions - Google Patents

Abstract

_ 1 _ HOE 90/F 319 Abstract of the disclosure:

Synergistic herbicidal compositions The invention relates to herbicidal compositions which contain A) the compound of the formula (I)

Description

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HOECHST A~TIENGESELLSCHAFT HOE 90/F 319 Dr.WE/fe Description Synergistic herbicidal compositions The inventien relates to the field o ~he crop protection agents which can be used again~t monoco~yledon and dicotyledon weeds.

~BI C 4874 ~I) with the chemical name (i~-tetrahydro-furfuryl ~2R3-2-[4-~6-chloroquinoxalin~-2 yloxy)pheno~y]-propionate is a herbi~idal ac~ive ~ubstance which czm be used post-emexgence for controlling annual and perennial grass weeds. Application xates of 5-250 g/ha, baxed on the pure active ~ubstance, control a large number of ; economically important graæs weeds in impoxtant dicotyledon crop species ~uch a~ ~oybean3, beet~, cotton, oil~eed rape, ~unflower~, peas, potatoe~, lentil~, flax, groundnut, etc. The crop plants tolerate the active substance which is used in ~he emul~ion concentrate~ for applica~ion without qualitative and quantitative change~.
The addition o~ paraffin oils, vegetable oil~ or wetting a~ent~ is indicated for u~e in practice to guaran~ee the action or to improve the action.

The active substance is known from publications/ ~or example A.R. Bell et al., Brighton Crop. Protection Conference-Weed~ 1989, pageæ 65-70.

Surprisingly~ some herbicidal active substances have now been found in biological tests which, when applied together with UBI-C4874, result in distinctive syner-gis~ic effec~ in ~he herbicidal activity.

The present invention relates to herbicidal compo~itions ha~ing a herbicidally effectivecontent of acombina~ion of A) the compound of the formula (I) :, . .

~ ~ O ~ ~ ~ C-o-CH~- ~ (I) and B) one or more c~mpound(s) from the group comprising the compounds B1~ 2-[4-(Ç-chlorobenzoxazol-2-yloxy)phenoxy~p~opionic acid (Bl) and the ester~ thereof, pxeferably the ethyl ester/

Cl ~ ~O-CH-COOI-i ( Ul ) '~ :
B2) glufosinate and the ~al~s ~hereof, pxefer~bly the monoammonium salt, O
H3C - P ^ C~2CH2CH - CO - OH (B~) O~

s3) herbicides which are mainly selective in seta bleet6 and are selected from ~mongst the group compri~ing phenmediph~m, desmedipham, ethofumesake, metamitron clopyralid and chloridazon, B4) herbicides which are mainly selactive in agri- :
culturally cultivated species from the legume ~amily such a~ soy~ean, field bean and phaseolus bean, and which are selected from amonyst the group comprising nitrodiphenyl eth~rs such as lactofen, acifluorfen and fomesafen, imi~azolinones such as imazethapyr and imazaquin, ~entazone and ~ulfonylureas such as amidosulfuron, chlorimuron and thiameturon-methyl, - . - .
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2~37~i B5) herbicides which are mainly selective in the agri-cultural crops flax and linseed and which are selected from amongs~ the group comprising hydro~y-benzonitxiles such as bromoxynil and io~ynil, and pheno~yacetic acid derivatives such a6 ~CPA, and B6) herbicide~ which are mainly selec:tive in the agri-cultural crops from the crucifer family such as oil~eed rape and turnip rape, and which are ~electe~
~rom amongs~ the group compri~ing carbetamide, di~.efuron, benazolin and its esters, metazachlo:r and propyzami~e.

All active substances have in common that they are preferably applied post-emergence and ta~en up via the green parts of the plant.
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Compound A ~compound of the formula I) is known rom the publication mentioned at the outset.

The eompound~ from groups Bl to B6 are known and mostly de~cribed in ~The Pesticide Manual", British Crop - 20 Protection Council, 8th Bd., 1987; for Bl ("~enoxaprop"
and "fenoxaprop-ekhyl"), ~ee page 379; for B2 : t"glufosinate")~ see page 488; for B3, see ~phenmediph2m~
on page 652, 6S3, ~desmedipham'l on page 242-243, "ethofumesate" on page 353-354, "metamitron" on page 536, "clopyralidl' on page 189-l90 and "chloridazon" on page 155-156; for ~4r see, for example/ "acifluorfen" on page 3, "fome~a~en~ on page 428, "imazethapyr" on page 475, "imazaquin" on page 474, "bentazone" on page 63-64; for B5 ~ee, for exampla, "bromox~nil" on page 100-102, ~ 30 "ioxynil" on page 479-482 and "MCPA" on page 514-517; for : B6, see, for example, "dimefuron" on page 293, "benazolin" on p~ge 51-52, "metazachlor" on page S37, ~ "propyzamidell on page 720 and "carbetamide" on pa~e 129.

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Some of the abov~mentioned ac~ive substances are described in Farm Chemicals Handbook ' 90, Meister Publishing Company, Willoughby, Ohio, US~ I99a, for example for B4, see common names "lac:~ofen" on page C 72, "chlorLmuxon~ and ~chlorimuron-ethyl~ on page C 720 "Thiameturon-methyl" corresponds to ~PX-MG316 t ~ee lFarm Chemical~ Handboolc, page C 152.

"Amidosul furon ", i . e . 3- ( 4 r 6-dimethoxypyrimidin-2-yl~
. (N-methyl-N-(methylsulfonyl)-aminosul~onyl)-urea ~8 a : 10 sulfonylurea herbicide for controlling dicotyledon weeds in cereals (c~. Z. Pfl. Krankh. Pfl./Schut~ Sonderheft [Special Issue] XII, 489-497 (1990)).

Fenoxaprop-ethyl is a herbicidal active ~ub~tanc0 for con~rolling grass weeds in agricultural crops such as soybeans, oilseed rape, sugar bee~, potatoes, inter alia.
It was fir~t described in D~ 2,640,730. In the meantime, it has been used in ~he form of the racemate and even as the op~ically active D(+) isomer (common name:
fenoxaprop-p-e~hyl). The racemate and P(~ omer and 20 their mixtures can ke employ2d accordin~ to the invention and come under formula Bl.

Glufosinate ammonium i~ a foliar-acting herbicid~ which is used po~t-emergencQ for controlling bro~d-leaved weeds and grass weed6 in pIantation crops and on uncultlvated land and, by means of ~peciic application technia~e~, also ~or treatment~ between rows in large-area agricultural crops such a~ corn, cotton, etc. Formula B2 also embraces the optical i~omer~ of glufosinate, in par~icular also L-pho~phinothricin and t.he ammonium salt thereof.

.~ Herbicidal COmpO~itionB according to the invention which contain the compound of the abovementioned farmula (I) and one of the compounds Bl to B6 are of particular interest .
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Other preferred herbicidal compositions are thos~ which contain the compound of the formula (I) in combination with fenoxaprop-ethyl, feno~aprop-P-ethyl, glufosinate~
ammonium or one or more compounds from among~t the group comprising phenmedipham, ethofumesate and metamitronf or one or more compounds from the group comprising lactofen, imazethapyr, imaza~uin and thiamethuron methyl, or one or more compounds from tha group comprising MCPA and bromoxynil, or one or more compounds rom amongst the group comprising carbetamide, dimefuron and benazolin or its esters.

The herbicidal compositions according to the invention have an excellent herbicidal activity against a broad range of economically important monocotyledon and dicoty-ledon harmful plants. The active substance combination also acts efficiently on perennial weeds which produce :~ shoots fxom rhizomes, root~tocks or other perennial organs and which are difficult ~o control. Speaifically, examples may be mention2d of some representativas of the ~` 20 monocotyledon and dicotyledon weed fl~ra which can be controlled by the compo~ition~ according to the invention, withou~ the enumeration being a restriction to certain species.
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Examples of weed specie on which the active substa~ce acts efficiently are, from amongst the monocotyled~ns, Avena, Lolium, Alopecurus, Phalarisl Echinochloa, Digi-taria~ Setaria and also Cyperus species from the a~nual ~ector and ~rom amongst the perennial species Agrop~yron, Cynodon, Imperata and Sorghum, and also perennial C~perus species.

In the case of the dicotyledon weed species, the range : of action extends to Galium, Viola, Veronica, Lamium, Chenopodium, ~triplex, Stellaria, Amaranlihus, Sinapi~, Ipomoea, Matricaria, Anthemis, Abutilon and Sida from amongst the annuals, and Convol w lus, Cirsium, Rumex and Artemisia in the case of the perennial weeds.
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If the active substance combinations are applied po8t-emergence on the green parts of the plan~s, growth likewise stops drastically a very short time after the treatment and the weed plants remain at the growth stage of the point of time of application, or they die com-pletPly after a certain time more or less rapîdly, so that in this manner csmpetition by the weeds, which is harmful to the crop plants, can be eliminated at a very early point in time and in a sustained manner by u~ing ~he novel composition~ according to the invention.

Even though the compositions according to the i~vention have an excellent herbicidal activity against monocotyle-don and dicotyledon weeds, crop plants of economîcally important crops, such as, ~or example, beets, oil~eed rape, field beans, so~eans, flax and others, are damaged not at all, or only to a negligible exten~. For these reasons, ~he compoæition~ are highly ~uitable fox selec-tively controlling undesired plant growth in plantings for agricultural use or in perennial cultures or in the non-selective sector. The area of use depends on the range of action or on ~he selçc~ivi~y of the individual active substances and can be roughly estimated from the known data on the individual actiYe substances.

The active substance combinations according to the invention allow, for example, a herbicidal action to be achieved which exceeds what would have been e~pected a~
an additive action of the individual componen~s. Such , improved actions allow the application rates o:E the ; individual active substances to be ~ubstantially redluced.
: 30 ~t comparable application rates, the synergistic e~fects make the controlled broad-leaved weed/grass weed range considerably wider. At the ~ame ~ime, p.roperties, which are of utmost importance in practical use, ara con~ider-ably improved in most combinations. This includes, for example, the speed of action, the long-term action, the flexibility in use, and others. This permits comprehen-sive, rapid, long-lasting and economical control of grass .~
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weeds and broad-leaved wee~s. Such properties ara econom-ically progressive because ~hey allow the us~r consider-able advantages in practical weed control by enabling him to control weeds more economically or faster or over a long period of time or with a lower number of individual applications to be carried out, and therefore to obtain higher yield~ in a stand of crop plants.

The mixing ratios A : B can vary within wide limits and are generally 100 : 1 to 1 : 1000, based on weight. The mixing xatio is selected as a function of, for example, the component in the mixture, the development stage of the weeds, crop species, grass weeds, range of weeds, en~ironmental factors and climatic conditions. It is preferred to use mixing ratios of from 15 s 1 to 1 : 700, in particular A : Bl from 10 : 1 to 1 5 : A : B2 ~rom 1 : 8 to 1 : 200 A : B3 from 5 : 1 to 1 : 700 A : B4 from ~5 : 1 to 1 : 400 2n A : B5 from 2 : 1 to 1 : 200 A : B6 from 1 : 4 to 1 500.

The application rates of herbicide A in the active sub~tance mixtures are prefexably between 5 and 120 g/ha, the application rates of the active substance~ fr~m groups Bl~B6 from 5 to 4000 g/ha, in particular, in the case of B1, from 5 to 120 g/ha, of B2, from 100 to 1000 g/ha, of B3, from 100 to 4000 g/ha, of B4, fr~m 5 to 2000 c3/ha, of B5, from 100 to 2000 g/ha~ and in the case of B6 from 500 to 1700 g/ha.

: 30 The acti.ve sub6tance combinations according to the invention can exist either as mixed formulations of the two, or of more, componen~s, and these are then applied in the customary fashion, namely diluted with water, or they can be prepared in ths form of so-called tank mixes by conjointly diluting the separately formulated :
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components with water.

The compounds A and B or the combinations t~ereof can be formulated in a variety of W8ys, as predetermined by the biologi~al and/or chemico-physical parame~ers. The following possibili~ies are there~ore ~uitable for formulation: wettable powders ~WP), emulsifiable concen trates (~C), aqu~ous solu~ion~ (SL), emul~ions ~EW~ ~uch as oil-în-water and water-in-oil emulsions, ~pr yable solutions or emulsions, di~per6ions on an oil or water base, suspoemulsions, dusts (DP), gramlles such as water-disper~ible granules ~WG), ULV fonmulations, micro-capsules or waxes.

These ahovementioned ~ormula~ion types are known in principle and are described, for example, in:
Winnacker-Kuchler, ~Chemische Technologie" rChemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Ed.
1986; van Valkenburg, IlPe~tioides Formul~tions~, Marcel ; Dekker N.Y., 2nd Ed. 197~-73; K, Martens, "Spray D~ying ~-~ Handbook", 3rd Ed. 1979, G. Goodwin Ltd. ~ondon.
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The formulation au~iliaries required, such as inert materials, surfactants, olvents and other additives, are ~: also known and are described, for example, in: Watkins, "Handbook of In6ecticide Dust Diluents and Carriars", 2nd Ed., Darland Books, Caldwell N.J.; H.~.Olphen, "Introduction to Clay Colloid Chemi~try", 2nd Ed., ~. Wiley & Sons, N.Y.; Mar~den, ~Solvents Guide"~ 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents ; and Emulsifiers Annual", MC Publ. Corp. Ridgewood N.J~;
Sisley and Wood, "Encyclopedia of Surface Active Agents~, Chem. Publ. Co. Inc., N.Y. 1964; Sch~nfeldt, "Grenz~l~chenaktive ~thylenoxidaddukte~ [Sur~ace-active Ethylene Oxide Ad~ucts]~ ~i83. Verlag~gesell~ Stuttgart 1976; Winnacker-K~chler, ~Chemische Technologie"
~Chemical ~echnology]~ Volume 7, C. Hau6er Verlag Munich, 4th Ed. lg86.

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g Combinations with o~her pesticidally ac~i~e substances, such as other herbicides, fungicides or insec~icides, and also safeners, fertili~ers and/or growth regulakors may also be prepared on the basis of the~e formula~ions, for example in the form of a readymix formulation or as a : tank mix.

Wettable powders are preparations which are uni~ormly di~persible in water and which, besides ~he active substance, also contain wetting a~ents, for example polyoxethylated alkylphenols, polyoxethylated fatty alcohols or fatty amine8 ~ ~atty alcohol polyglycol ether sulfates, alkanesulfonates or alkylbenzenesulfonates, and dispersing agents/ for example sodium lig~insulfonate, ~odium 2/2'-dinaph~hylme~hane-6,6'-disulfonate, ~odium dibutylnaphthalenesulfonate, or ~lternatively sodium oleylmethyltaurinate, in addition to a diluent or inert ~ubstance.

Emulsifiable concentra~e~ are prepaxed by di~solving the ~: active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, ~ylene and ~ also higher-boiling aromatic compounds or hydrocarbons, : with the addition of one or mor~ emulsifiers. ExamplQs of emulsifiers which can be used are: calcium salts of an alkylarylsulfonic acid, such as Ca dodecylbenzene-: 25 sulfonate/ or non-ionic emulsifiersJ such as ~atty acid polyglycol esters, alkylaryl polyglycol ethers, fatty . alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, ~orbitan ~at~y acid esters, polyoxyethylene sorbitan fa~ty acid esters or polyoxyethylene sorbitol esters.

~u~t~ are obtained by grinding the ac~ive ~ubstance with fi.nely divided solid substances, for example talc or : nakural clays, such a~ kaolin, bentonite and pyrophyllite or diatomaceous earth.
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Granules can be pxoduced either by spraying the active , .
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substance onto adsorptive, granulated inert material or by applying active substance concentrates onto the surface of carriers, such as sand, kaolinites or granulated inert material, by means of binders, for example polyvinyl alcohol, sodium polyacrylate or, alternatively, mineral oils. Suitable active substances can also be granul~ted in the manner which is conventional for the production of fertili~er granules, if desired in a mixture with fertilize:rs.

The a~rochemical preparations generally contain 0.1 to 99 percent by weight, in particular 2 to 95 % by wei~ht, of active substances ~ + B~ The concentrativns of the active ~ubstances A + B can vary in the formulations.

The concen~ration of active substance in ~ettable powders is, for example, about 10 to 95 % by weight; the remain-der ~o ~00 % by weight is composed o con~entional formulation components. In the case of emulsifi~ble concentrates, the concentration of active substance can ba about 1 to 85 % by weight, preferably 5 to 80 ~ by 2~ weight. Formulations in the form o~ dusts contain about : 1 to 25 % by weight, usually 5 to 20% by weight o~ active substance, sprayable solutions about 0.2 to 25 ~ by weight, preferably 2 to 20% by weight. In the case of granules such as water-dispersible granule~, the active substance content depends partly on whether the active compound is liquid or solid and on which granulation auxiliarie~ and fillers are used. As a rule, tha content : in the water-dispersible granules is be~ween 10 and 90 %
by weigh~.

In addition, the active substance ormulations mentioned contain, i~ appropriate, the adhesives, wetting agents, dispercing agen~s, emulsifiers, penetrants, solvents, fillers or carriers which are conventional in each case.
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For use, the formulations, present in commercially available form, are diluted, if appropriate, in a :
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customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusts or granules for soil application and for broad-:~ 5 casting and also sprayable solution~ are usually nnt further dilut~d with other inert sub~ances before use.

The application rate required for the compounds of the formula I varies with the ex~ernal condi~io~s, s~ch a~, inter alia, ~emperature, humidity, ancl the nature of the herbicide used.

The examples which follow 6erve to illustrate the inven-~ tion:

;~ A. Foxmulation Example~

a) A dust is ohtained by mixing 10 parts by weight of an active ~ubstance combination according to the : invention and 90 paxts by weight of talc as inert :~ sub~tance and comminuting the mixture in a hammer miIl.
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b) A wettable powder which i~ readily dispersible in water is obtained by mixing 25 parts by weight of active substan~e A + B, 64 parts by weight of kaolin-containlng quar~z a6 the inert substance, 10 parts by weight of potassi~m lignin~ulfonate and 1 part by weight oF ~odium oleoyImethyltaurinate a6 ;` 25 the wetti~g and dl~persing agent, and grinding the mixture in a pinned disk mill.

c) A dispersion concentrate which is readily di~pers-ible in water i~ obtained by m.i~ing 20 parts by weight of active sub~tance A + B with 6 pa.rts by weight of alkylph nol polyglycol ether (Triton X
; 207), 3 parts by weight of isotridecanol polyglycol : ether (8 E0) and 71 parts by weight of paxaffinic : mineral oil (boilin~ range, for example, about .~ .
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255 to above 277C~, and grinding the ~i~ture in a ball mill to a fineness of below 5 microns.

d) An emulsifiable concentrate is obtained from 15 parts by weight of active substances A~B 75 parts by weight of cyclohexanone S as the solvent and 10 parts by wei~ht of oxethylated nonylphenol as the emulsifier.

e) Water-di~persible granules are obtained by mixing 75 parts ~y weight of active substances A ~ ~, 10 " of calcium ligninsulfonateJ
5 ~ of sodlum lauryl su}fat2, 3 " of polyvinyl ~lcohol and 7 " of kaolin, grinding the mixture o~ a pinned disk mill, and ; granulating the powder in a fluidized bed by spray-1~ ing on water as the granula~lon li~uid.
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f) Water-dispersible granules are al~o obtained by homogenizing and prec~mminuting on colloid mill, 25 parts by weight of active sub~tances ~ ~ B, 5 " of sodium 2,2'-dinaphthyl-mathane-6~6'-disulfonate, : 2 " of sodium ole~ylmethyltaurinate~
1 part by weight o~ polyvinyl alcohol, 17 parts by weight o~ calcium carbonate and " of water, ~ubsequen~ly grinding the mixture on a bead mill, an~ at~izing and drying ~he re~ul~ing ~uspen~ion in ~ a spray tower by mean~ of a single-compound noz~le.
,, For example, the active substance combinatione from Table 1 below are formulated ~ollowing the formulations ~:
de~cribed under a) to f):

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Table 1 ~ctive substance A Active subs~ance B Ratio AqB

(I) Fenoxaprsp~P-~thyl 10:1 1:1 1:5 tI ) Glufo in~te- 10:1 ammo~ium 1:1 1:5 tI) Phenmedipham 5:1 1:1 1:10 ~I) Lactof~n ` 15:1 ,: 5:1 ': ' 1: 1 1:100 (I~ Bromoxy~

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2~0 enazoli~-ethyl 5:1 2:1 -:~, 1:10 . .
B. Biological Exampl~s :
Under ~ield ~onditions, trial fields with sandy loam 80il were seeded with ~in~er oilseed rape (BRSNW) ~ollowing customary a~riaultural practices (seediny time August, seed den~ity 5 kg/ha, fertilization ~ollowing customary agricultural prac~ices?~ ~fter the crop plants had emerged, a high degree of infestation with A~ropyron repens ~AGRRE) and volunteer barley (HORVW) became ,, ~

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apparent. When these grass weeds were in the 1- to 3-leaf stage, or when tillering began (21), the active substance combinations accQrding to the invention which had been formulated in the form of wettable powders or emulsion concentrates and, in parallel trials, the corre~pondîngly formulated individual active substances (~ee Table 2~
were then applied in the form of aqueous ~uspen~ions or emulsion~ to the surface of the trial area, using an application rate of 300 to 800 l of water/ha ~converted) in various dosages.

40 days after application, ~he Aerbicidal effects were determined by visual scori~g o~ ~he damage to the plant~
compared with untreated plant~. In all cases, the ex~eri-menter dis~inguished between the calculated and the ~ound degree of effec~i~eness in th~ combinations. ~he calcu-lated degree o effectiveness of a combination, which was to be expected ~heoretically~ is determined by S.R. Colby~ formula: Calculation of ~ynergi~tic and antagonistic response~ o herbicide combination~, Weeds 15 (1967) 20~
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;:- This formula read~:
,~ , X Y
E = X + Y - -; 25 where X is % damage by herbicide A at an application rate of x kg/ha;
Y i6 ~ damage by herbicide B at an application rate of y kg/ha;
E = damage by herbicide~ A + B to be expected at a rate of x ~ y kg/ha.

If the ~ctual damage is greater than the damage to be expected following calculations, then the action of the combination i8 ~up~radditive, i.e. a synergis~ic effect . , .

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of action exists.

The active substance combinations according to the invention have a herbicidal action which i~ greater than would have been expected based on the actions of the individual component~ ob~erved when u~ed by ~hemselYe~.
The active substance combination~ therefore ~how synergistic behavior (cf. Table 2).

Table 2: Active substance combination UBI-C 4874 (I~
plu~ fenoxaprop-P-ethyl % damage 40 days after application tstage of application]
Active Dosage AGRRE HORVW BR5NW
~ubstances rat~
Cg of ai/ha~ tll-2~ ~13] [1 -- .

5& 86 0 4~ 67 ~8 ~S 0 ~: .Bl.1 lS 0 20 0 - 30. 0 2V 0 '45 3 27 0 IIBl.l lS~lS 77 (43) 58 (48) 0 15~307a (~6) 80 (4~) 0 15~5 ~3 (~S) 87 ~53~ 0 30+1573 (43) 89 (88) 0 30~308~ (56) 92 (88~ 0 30+~588 (~7) g5 (8g) 0 45+15~6 (43) 95 ~90) 0 ~5~30g2 (56~ 97 (90) 0 ; _ 45+4S 94 (64~ _ 98 ~

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Table 2, abbreviations:

I = UBI-C 4874 as a 12 % emulsion concentrate (EC
120) and 5 l/h oil s1.1 = fenoxapxop-P-ethyl as a 7.5 % oil-in~watsr emul~ion ai = active ingredient (based on pure ac~ive ~ub-stance) ( ) = expected value an according to Colby Table 2 ~hows that the herbicidal activity of UBI-C 4874, applied a~ mi~ture with oil/ i5 markedly increased when applied together with fenoxaprop-ethyl. I~ the case of :~ Agropyron repen~ ahd ~olun~eer barley, there exi~t synergistic increases in action. In the case of Ayropyron ~, repens, the action o the herbicide combination~ even exceeds the formal sum of the action of the indivi~ual active substances. In the case of volunteer barley (HORVW), the expected values of the herbicide . combination~ calculated theoretically by COLBY'~ formula, ~ are also clearly exceeded in the trial. ~`

:~ 20 The crop compa~ibility in the csse of winter oilseed rape (B~SNW) is nei~her impaired by the individual ac~ive substances nor by~he herbicide combinations.

Example 2 Under natursl field conditions, annual grass weeds had emerged on uncultivated land.

When developmen~ stages 25 to ~9 (middle to end of tillerin~ phase) had been reached, the he~bicides given ;~ in Table 3, on their own and in combination, were applied ~i to parts of plots of size 10 m2 u~ing plo~ sprayers (analogously to Example 1). 28 days ater application, the herbicidal activity of the treated parts of plotc was recorded by visual scoring (analogously to ~xample 1~ in comparison wlth ~he untreated control plots. Plant ;. .~
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damage, and plant growth and development, were evaluated in percentage~.

The result~ are compiled in Table 3.

Table 3: Active ~ubstance combina~ion UBI-C 4874 (I) plus glufo~ina~e-ammonium % damage 28 day~ after applica-tion [~tage of application]
Active Do~age PHAMX PHAPA HORV5 BRVDI
~ubstances rate [~ of ai/ha] E2s~ [25~~29] ~9]

: ~ 30 15 0 ~2 65 B2.1 . 300 50 40 27 35 600 97 g~ 65 ~5 , .
I +B2 .1 30t300 95 94 100 100 ` :
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, Table 3, abbreviations-I = UBI-C 4874 as a 1~ ~ emulsifiable concentrate B2.1 a glu~osinate-ammonium as a 20 % aqueous solution : ai = active ingredient based on pure active substance .~ .
The activity o the herbicide combination .i8 clearly above the action of the individual active substances ~nd iR comparably good, or even bett0r, than the action of twice the application rate o glu~o~inate ammonium on its own. ~he synergistic e~fects allow a better and broader activity to be achieved with ~maller amounts o~ active sub tance.

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Example 3 Sugar beets were grown on trial :Eields following c:usto-mary agricultural practice ~ When the sugar beet~ ( BE~W ) had emerged, a high degree of infesta~ion with cockspur grass (~chinochloa crus galli - ECGCR) and wild oat~
~Avena fatua = ~VEFA) became apparent.

In the develo~ment ætage mid-tillering ~E 25~ to end of tillering (E 29), ~he herbicides on their own and their combination were applied analogously to Example 1 using plot sprayer~ (300 litexs of w~ter/ha~. 14 days, or 28 days, after the applicAtion, the herbicidal effects on : the grass weeds or crop plan~s were determined by visual scoring.
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: 15 Table 4s Active æubstance combination UBI C 4874 (I) ' pIus phenmedipham " .
~ damage at [~tage of application]
., Active Do~age ECGCR ~VE~A BEAW
: ~ub~tance~ rste : 20 development in g o~ [6-8 ;~ stage at ai/ha ~25-29] t25-29] leaves3 ` application ~5 0 :B3 . 1 ~42 10 25 0 1256 15 . 75 0 I~B3.1 30+942 75 (23) 85(74) 0 ~ _ _ 60~g42 98 ( 91 ) g7 ( 89 ~

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.

. .
. . .

:
:

2~3~

Table 4, abbreviations:

I - UBI C ~874 together with 2 l/ha oil B3.1 = phenmedipham together with 2 l/ha oil I~B3.1 = UBI-C 4874 ~ phenmediph~m + 2 l/ha oil ( ) = expec~ed value according to Colby The resul~s show that in ~he case of ~oint application - the herbicidal activity is marXedly above the effects of ~he herbicides on their own, even at higher application rates. The expected values according to COLBY are clearly exceeded.

Besides, both grass weeds are controlled with equally good activi~y, in contrast to khe application of the individual active substances, which allows the synergis-tic effects to broaden the r~nge of action while simul-taneously reducing ~he active ~ubstances.

~: The crop plants are damaged neither by the harbicides on their own nor by the combination thereof.

Claims (10)

1. A herbicidal composition having a herbicidally effective content of A) the compound of the formula (I) (I) and B) one or more compound(s) from the group comprising the compounds B1) 2 [4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propionic acid (B1) and the esters thereof, preferably lethyl ester, (B1) B2) glufosinate and the salts thereof, (B2) B3) herbicides which are mainly selective in Beta beats and are selected from amongst the group comprising phenmedipham, desmedipham, ethofumesate, metamitron, clopyralid and chloridazon, B4) herbicides which are mainly selective in agri-culturally cultivated species from the legume family and which are selected from amongst the group comprising nitrodiphenyl ethers, imidazolinones, bentazone and sulfonylureas, B5) herbicides which are mainly selective in the agri-cultural crops flax and linseed and which are selected from amongst the group comprising hydroxy-benzonitriles and phenoxyacetic acid derivatives and B6) herbicides which are mainly selective in the agri-cultural crops from the crucifer family and which are selected from amongst the group comprising carbetamide, dimefuron, benazolin and its esters, metazachlor and propyzamide.

2. The composition as claimed in claim 1, which contains a compound of the formula (I) and a compound from amongst the groups B1 to B6.

3. The composition as claimed in claim 1 or 2, which contains 0.1 to 99 % by weight of the active substances A and B, besides customary formulation auxiliaries.

4. The composition as claimed in one or more of claims 1 to 3, which contains the active substances A and B in a ratio by weight of 100 : 1 to 1 : 1000.

5. The composition as claimed in claim 4, in which the ratio by weight is 15 : 1 to 1 : 700.

6. A process for preparing a composition as claimed in one or more of claims 1 to 5, which comprises formulating one or more compounds A with one or more compounds B analogously to a customary crop protection agent formulation from the group comprising wettable powders, emulsifiable concentrates, aqueous solutions, emulsions, sprayable solutions (tank mix), dispersions on an oil or water base, suspoemulsions, dusts, water-dispersible granules, ULV formulations, microcapsules and waxes.

7. A method of controlling undesirable plants, which comprises applying a herbicidally effective amount of one of the combinations of active substances A +
B, defined in one or more of claims 1 to 5, to these undesirable plants or their cultivation areas.

8. The method as claimed in claim 7, in which weeds in crops of useful plants are controlled selectively.

9. The process as claimed in claim 8, in which the crop of useful plants is from amongst the group of the dicotyledon crop species or perennial crops.

10. The use of the herbicidal agent as claimed in one or more of claims 1 to 5 for selectively or non-selectively controlling weeds.