SE446928B - AGENTS WITH HERBICIDE EFFECTIVE CONTAINING 0- / 3-PHENYL-6-CHLORPYRIDAZINYL- (4) / - S- (N-OCTYL) THIOCARBONATE IN MIXTURE WITH 4-HYDROXY-3,5-DIODEBENZONITRIL-OCTANOATE AND / OR 4 -3,5-DIBROMBENSONITRIL-OCTANOATE AND USE - Google Patents

Description

446 923 1 hicidn properties and is characterized by a good contract harhët'Tör many nyltovñxtur, bl n südcskulturvr. In particular, the compound O- [E-phenyl-o-chloro-pyridazinyl- (4L / ~ S- in-octyl-thiocarhonal ("Pyridate") has been shown to be an active agent for controlling weeds in southern and maize crops (Diskus o. 'mcdarh., Proc. 9th British Weed Control Conf. 1976, Vol 2, 717) and comprises a hrctt spectrum of weeds.

In practical use in the open air, however, it turns out that some weed species such as Stellaría media and Polygonum convolvulus could only be controlled with relatively high doses of active substance or, as Papaverrhoeas was generally difficult to control. This is especially the case when weeds are in a state of advanced development. It is further known that compounds of the group 3, S-dihalo-4-hydroxyhensonitriles show good properties as contact herbicides (Nature, London, 1963, Vol. 200, p. 28). In particular, octyl esters of the compounds 4-hydroxy-3,5-diiodobenzonitrile ("Ioxynil-octanoate") and 4-hydroxy-3,5-dibromobenzonitrile ("Bromoxynil-octanoate") were used in molten, broadleaf weeds after treatment. germinating (H. Martín, CH. R. Worthing, "Pestícíde Manual" 5th edition 1977, pp. 293 and 54). However, a number of weeds with increasing age become more resistant, so that for their control must be used These weeds include Galium aparine and Galeopsis tetrahite (H. Kurth, "Chemische Unkrautbekämpf- ung", Fischer Verlag Jena, 1975, p. 170).

It has now been found that mixtures of active substances belonging to the group of phenylpyridazines of the general formula I, in particular the compound O- [ε-phenyl-6-chloro-pyridazinyl * (41] -5- (n-octyl) Pyrotate, with active substances from the group 3,5-dihalo-4-hydroxyhensonitriles, in particular the compounds 4-hydroxy-3,5-diiodobenzonitrile octanoate ("Ioxynil-octanoate") and 4- hydroxy-3,5-dibromobenzonitrile octanoate ("Bromoxynil-octanoate") gives a herbicidal efficiency which is significantly above the efficiency which could be expected due to the exclusive additive action of the two components. thus of a genuine synergistic effect, which to that extent could not be foreseen in any way and which must be considered as particularly surprising.

The object of the present invention is thus an agent with a hydride action, which is characterized in that it has as active ingredient dininyl in the compound O- / E-phenyl-h-chloropyrid ß-sinin-4,446,928 (4X7-S- (n-octyl) thiocarbonate in admixture with the compound 4-hydroxy-3,5-diiodobenzonitrile octanoate and / or 4-hydroxy-3,5-dibromobenzonitrile octanoate in a mixing ratio of from 1: 1.6 to 110.1, the amounts in the hydroxybenzonitriles are given in phenol equivalents.

Through this, in addition to a purely additive effect extending, increased herbicidal efficiency of these mixtures of active ingredients, significant technical advantages are obtained, since it is thereby possible to significantly reduce the amounts used and thus the costs of the individual components used. per treated surface.

The compound O- [E-phenyl- 6-chloropyridazinyl- (4I7-S- (n-octyl) -thiocarbonate ("Pyridate") gives significant increases in efficacy in combination with the compounds 4-hydroxy-3,5-diiodobenzonitrilobctanoate ("Ioxynil octanoate ") and / or with 4-hydroxy-3,5-dibromobenzonitrile octanoate (" Bromoxynil octanoate "), whereby good results are obtained.

The compositions of the invention may be converted into conventional preparations, such as solutions, emulsions, dispersions, powders, pastes and granules. These are prepared in a known manner, for example by mixing the active substances with fillers, ie liquid solvents and / or solid carrier materials, possibly using surfactants, ie emulsifiers and / or dispersants. As solid carrier material, essentially rock flours, such as kaolin, clays, talc, chalk and synthetically produced rock flour products, such as highly dispersed silicic acid and silicates; Suitable emulsifiers are nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, alkyl sulfonates, aryl sulfonates and alkyl aryl sulfonates; lignin sulphite liquors, methylcellulose and Na-oleyl-methyltauride are suitable as wetting and dispersing agents.

The proportions of the compound of the formula I in the mixture to compounds of the formula II (phenol equivalents) may vary within a certain range, for example in the ratio from 1: 1, 6 to 1: 0, 1, mixtures in which the proportion compounds of the formula I consider, in particular, to be preferred- The combination of active substances according to the invention can, for example, be formulated according to the following recipes as a spray powder or as a c-emulsion concentrate: 14-50% by weight 3-20% by weight (calculated on fe- Active substance of the formula I Active substance of the formula II nol equivalents) -15% by weight ad 100% by weight Hydrogen or dispersant inert fillers or carrier materials.

This composition is suspended or emulsified when used in water. It may also contain other known active substances, such as herbicides, fungicides or growth regulators. Particularly favorable is a combination with active substances from the group of phenoxycarboxylic acids, such as "MCPA", "GMPP", "2,4-DP" and "2,4-D" and their saline or esters, respectively, since with them also perennial weeds can be combated in a work operation.

The agents of the present invention are used in post-emergence treatment procedures. The amounts of active substances used in the combination can also be varied within a certain area. They depend on the composition of the combination of active substances and the type of weed. Usually the active substance of the general formula I is used in an amount of 0.25 to 1.0 kg / ha and the active substance of the general formula II in an amount of Q, to 0.4 kg / ha.

Particularly preferred is a use of the compositions according to the invention in cereal or maize cultures, wherein the active substance of the formula I is introduced in an amount of 0.5 to 1.0 kg / ha and the active substance of the formula II is introduced into a amount of 0.2 to 0.4 kg / ha. 'To determine whether a mixture has additive or synergistic effects, the following formula is usually used E' = x + Y -% ¿š (according to LE Limpel, PH Schuldt, D. Lam0nt, .l962, Weed control by dimethyltetrachloroterephthalate al flfl ë in d in Ceft fl í fi C0mbiHa "tions, Proc. NEWCC 16: 48-53, based on DP Gowing 1960, Comments on tests of herbicide mixtures, Weeds 8: 379-391).

E = (in case of additive effect) expected herbicidal efficiency (% herbicide destruction) after use of A + B at p + q kg consumption / ha. s 446 928> <II efficiency (%) when using the active substance A with p kg / ha. efficiency (%) when using the active substance B at q kg / ha.

If the experimentally obtained value for E is above the value calculated above the above formula, then there is a synergism, and if the value is below it, there is an antagonism.

From the results in Tables 1-S it is clear that in practically all cases when combining the active substances I '+ II' resp. In '+ III' the herbicidal efficiency (% killing) is significantly above the expected (calculated) values with pure additive effect. The practical benefits of a synergism to the extent documented here are extremely great. As is known, the "EWRC" herbicidal efficacy assessment scheme is based on an approximate exponential function between the efficiency (% killing) and the actual value number in such a way that in the practically usable range between 85 and 100% killing a significant more differentiated registration takes place than in the economically uninteresting area between 0 and 85% killing (see "EWRC" assessment schedule).

An increase in efficiency in the upper area is therefore significantly more significant than in the lower area. An improvement in efficiency from eg 95% to 100% (+ 5%) corresponds to an improvement with two evaluation steps, whereas an increase in efficiency from eg 70% to 80% (+ 10%) only corresponds to a rating step and also practical is of little importance (both 70% and even 80% killing still applies as insufficient).

As can be seen from the following examples, however, in the area between 85% and 100% killing in particular, synergistic increases in efficacy can be determined to a economically significant extent.

The example further shows that even at a used amount of 0.2 kg / ha of compound I '("Pyridate") and of 0.1 kg / ha of compound II' ("Ioxynil-octanoate") the herbicidal efficiency is at all weeds tested significantly exceed the effect of the sum of the individual components. The synergistic effect in this case is extremely clear; thus it is, for example, at the weeds Galeopsis tetrahit, Lamíum purpureum and Veronica hederífolia at +26, +27 and +29 r.

Lfl 015 zn _Lamium purpureum - 4460928 6 Of great practical importance, when combining 0.25 kg / ha of compound I * with 0.2 kg / ha of compound II ', the increase in efficiency compared to the heavy-duty Galium aparine is 98% killing, which already corresponds to a very good effect according to the "EWRC" scheme. In a combination of 0.5 kg / ha of compound I 'with 0.2 kg of compound II', with the exception of Polygonum convolvulus, all weeds, and in particular Galium aparine up to 10oa%, are already killed. "'Compound III' (" Bromoxynyl-octanoate ") is very similar in its chemical, physical and biocidal properties to compound II '(" Ioxynil-octanoate "). Accordingly, the synergistic effects are also very similar, as shown in Tables 4 and S.

Examples Rectangular small plastic boxes (35 X 38 X 7 cm) were used as survey units, in which the weeds in question were planted. The following, consistently economically significant arable weeds were used in the surveys.

Chenopodium album a 7 - Galeopsis tetrahit ~ Galium aparine _ '- Lapsana communis Lithospermum arvense I a Matricaria chamomílla - Papaver rhoeas - Polygonum convolvulus - ll w »a: av w rn U cw uø \> Stellaría media - Veronica Leder _oleder weeds have reached the state of development at which they are usually treated in seed crops with herbicides according to the post-emergence treatment procedure (Galium aparíne eg branched, with 3-6 wreaths / side shoots, Lapsana communis in 6- to 8-leaf stage, Matricaria chamomilla in 8- to 10-leaf stage, Stellaria media already branched with 4 to 6 leaf pairs per side shoot, Galeopsis tetrahite with 2 to 3 developed leaf pairs, etc.), active substances or combinations of active substances were sprayed in specified dosages on weeds. The amount of spray preparation was uniformly 500 l / ha. 4 weeks after spraying, the herbicidal efficacy 70.0 1 446 928 was determined. The remaining weeds were harvested — separated by weeds — and their fresh weight was determined. In the same way, weeds are fed into the comparison boxes that have been left untreated.

The remaining weed growth after treatment was set in relation to the weed growth in the untreated boxes and in this way the current herbicidal efficiency (% killing) was determined.

These values were then examined in the case of product mixtures based on the formula according to Límpel for the presence of possible synergistic effects.

The compound "Pyridate" was used in the following composition: In% active substance 7.5% alkylarylsulfonate-polyoxyethylene emulsifier mixture zz, s r solvent The compounds "Ioxynil-octanoate" resp. is used as the following preparation: "Bromoxynil-octanoate" Active Emulsifier Mixture of aromatic hydrocarbons "Ioxynil-octanoate" 47.2% 4.38% 100% (equivalent to 400 g / l phenol equivalents) "Bromoxynil-octanoate" 51 .08% 4.38% 100% (corresponding to 400 g / l phenol equivalents) The data regarding kg / AS / ha in the tables refer to "Ioxynil-octanoate" resp. "Bromoxynil-octanoate" to current equivalents of free phenol. .mß oo fl oo fl wo mm ow NN oo fi oo fi .HHH u ~: Hmo: muuo | HNc> xoEowm: v «.o mm Nm Nm mm Nm ON mm cm mm No N« ° = «» N ° NN mN om NN Nm NN om om NN N. ° »NNN» N = om = w @ soN @ -N @ -mm-Nx0N @ Nn- «.HH n mm QQN NQN mN mm mN mm QQN AND m. @ N = ~ mo = @ @ N ° -NN = NxQN = V mN Nm mN Nm om mm Nm mm NN N. ° N «°: m» N0-NNNNN = @ m = @@ Nm Nm ON mN NN om mm CN mm N. = - @ QNNw «mm-Nx0N @ N; -N .EU mZQUUNÜHHXQ-L, mN mm mm .DON DON OON mm QON OQN oN Nm = ° @ N ~ N mm mm Nm mm NN mm mN NN mm mo -om» -NN> NM ° - = Vw | cm GN Cm Nm mm mm Oø mm mN mN.Q -NNNU1NN = NNmwNNN @ -NoNz-m-NN = @ N-mN-o 446 928 N = o NNQUN <@: Nm <NN N wc fl hmmon .NN mmwwc> w wdm : wæm> <øcsm uEmmxHm> fi fifl mnææ 446 928 _g_ m + m + m + 1 | m + 1 ß + m + 1 | mconowm fi u ßm _ßm Hm oo fi cc fl Nm oo fi mm wo oo fi oo fl uwnxmmmn oc fi oo fl oc fi oc fi oc fi oo fi oc fi oo fl oo fl co fi oc fi uo fi cßm v «om + ß + m + m + m + m + w + m + w + mm No mo Mm mm wc ææ Nm Hm ßm uw fl xwhøß oo fl oo fi mm oo fi co fi oo fi cc fi oo fi oc fl co fl oo fl uo fi cäw No + <+ m + cH + w + H ~ + m + m + ß fi + c + oH + m + m ßwom Nm mæ mo mo mo mo vw do mm uwaxmhun. , _ om oc fl co. oc fl cc fi wo oo fi oc fi om co fl oo fi umnc fi m fl c + m o m + w + w + 1 | v + 1 N fi + «+ 1 | møwnømu fi w mm om om co fi oc fl om oc fi ww om oo fl oo fl pw fl xmnon oc fl cow cow oo fi co fi cc fi oo fl co fi coq oo fl com uoznñw «.o + w + m fl + w + ß + m fi + m + m + mH + H + H + H Nm oo fl mm cow co fi wo con oc fi wo oc fl oc fl wwønäw N c + mm + flfi + oH + o fi + ma + w + m + ßm + w + oN + HH + wcouoom fl o om fw ww mw ßw mm mn mn mn om wøcmmnwß mm co fl wo cc fi mm wa oo fi ßw wo oo fl wvzczm fi. c + mN.o 4 1 H: 0 wm QU m <m @ \ m <wc wc fl nwmow w M wmuwo> mw: fi: ooo>% .conëm wEEmmM @ w> _10 .. 446 928 H + H + ~ + .i C f | | 1 | 1 I mcwhmww fi w CC CC OO AND AND AND AND AND COH AND AND OOOHOHOO AND AND AND AND AND AND COH AND AND AND H @ C == H O.O + m + m + o m + H + 1 | | n | | mcwnmmm fi w OC HC CC HC OO AND AND AND AND AND AND AND HOCHOHOO AND AND AND AND AND AND AND AND AND AND HOCCCH HHC + OO + O + _ HH + OH + a - - H + - - OOOHOHHHC HC OC HO OC CC AND AND AND CC AND AND HOCHOHOO AND AND AND AND AND AND AND AND AND AND HOCCOH HO + CH H H. H: COHOOC <.HH + .H OH \ w <OH m: HHwmou w M mmnwo> m wG fl C fi wU> <fl wñäm dEEmmMh0 > m H fl osmh. 446 928 _11 ..

N + m + a + | a m + .T O. + o + | .. mcwhwmm fi w CO Om HO CCH AND mm OC Om OC AND CCH ~ m = HwHw @ A _ CCH CCH CCH CCH CCH CCH CCH CCH CCH CCH CCH CCH ~ @ ==: HOO + C + N f OH + O + O + O + m + CH + C + HH + O + m = m »@wOHO NO _ NC HC NO OC OC OC CC. CC OC OO H «= HmC @@ CO OC CCH CCH CCH CCH CCH CCH CCH CO CCH CCH H @ ==:« ~ .C + O + C + NH + m + O + w + O + CH + O + O + H + mn @ H @ wHHO OC OO mO WO OC OC OC HC WO OC OO OCCHWHÜC MC OC OC Om CCH Om CCH HO OO mm OO Hwuøsm HC + mC N + m + CH + | | w + H + HH + O + - 1 mn @ H @@ wHO CO mm CC CCH CCH OC CO OC HO AND CCH ~ mcHmH @@ AND AND CCH CCH AND CCH AND AND CCH CCH AND H @: = aH OC + O- ~ H + O + HH + O + O + O + OH + OH + CH + C + mø @ H @ «HHC OC CO OO OC CC NC OO CC OC OC NC HC: Hw» @@ NO CCH OO CCH CCH mm OCH CCH OO CCH CCH Hwøcsw NHC + OH + CH + C + C + CH + O + HH + m ~ + C + OH + ~ H + MCCHCHHHC OO OC OO CO CO OO CO CO NO OO OC HCCHOHQQ _.

Om OO CO OC CCH N CCH Om OO OC OC Hwqn = H H C + m ~ .O H H H: C O O C C C <HH ~ H + .w HO H mmuuo> m HHHJHHHOQHCOCHH mHÉmHH. u; wcfwv. . cwcëm mšämw fl ë, 446 928 H + .N +, @ + 1 1 1 1 1 1 1 1 mcmæwww fifl mm wo wa oo fi oo fi oo fi oo fi Qo fl oo fl oo fl oo fi »æcxmswn. oo fl oø fl oo fi oo fi oø fi ooñ oo fi oo fi oo fi co fi ao fi wmcøsm wo + m + w + mm om om wa oo fi oo fi oo fl oo fl mm oo fl oo fl pmcxmpmn _ cø fi oo fi oø fi oo fl oo fi m m m fi fi fl fl fi fi fi fi fi fi ø ø fi fi fi fi fi fi fi fi fi fi fi fi fi ~; + ~ + 1 1 1 fl1 1 1 mcwwmww fl v om ma om wæ mm oo fi oø fl oø fi mm QQH oo fi pwczmuon. .

N N Nm mm oo fl QQH oo fi QQH. wa: OH oo fl gepccnw H Q + Q H A M H I w .A ... M: _ U w <.E11 w Q mwumo> m mc fi awmw> <. m; \ w <mg w: «puwov 1w Hñwßmw ß fi üüåm GE§ flfi Ahü> 13" EWRC "assessment scheme: Värdetal Killing of weeds 446 928 Effect of a preparation IQO%" * O \ lw: W f _ Jifâßïírë .-- very good 3.9.4 ko 'O: (too u: * ån (Il <, \ ° - = ~ °' @ n U1; i IPI - u O \; \ I uuu-x u fi gn-f- _ , _4. -Vi __ »...._......« -_ - ...._.....__- -> ~, ._.._ «w» ~ _ _ - __, n __- -_ _w, __ ~, h_ I 7 rlnga 8 32.5% É very little none. åliziàsïäääëšälíe_ yet sufficient nod sufficient "446 928 14 Comparison of the herhicidal vorknn nv a mixture of O- / 3 ~ Fcny1 -o-chloropyriduzinyl- (4) [-5- (n-octyl) -thiocarbonate ("Pyridute") with 4-hydroxy-3,5-diiodonsononitrile octunoate ("loxynyl) -octonoate" 1 or 4-hydroxy-3 5-Dibrombsononitrile octanoate ("Bromoxynil octanoate") having the herbicidal action of a mixture of "Pyridate" with Ioxynil-Na-salt or Bromoxynil-Nn-salt.

Rectangular small plastic boxes (35 x 38 x 7 cm) were used as experimental units, in which the weeds in question were planted.

The following economically significant acergrass was used in the surveys: Ä I Chonopndinm album = 'Galeopsis tetrnhít = Galíum aparíne = Remium purpureum = THÜFDW> Lapsana communis = Lithospermum arvense = Mntricaría chamomilla = Papaver rhovol nia = Hia> Vernica hederífolia = L Since the weeds had reached the state of development at which they are usually treated in seed crops with herbicides according to the treatment procedure after germination (Galium aparine eg branched, with 3-6 wreaths / side shoots, Lapsana communis in 6- to 8- leaf stage, Matricaría chamomilla 1 8- to ln-leaf stage, Stellaría media already branched, with 4 to o leaf pnr per side shoot, Galeopsis tetrahite with 2 to 3 developed leaf pairs etc.), the active substances were sprayed resp. combinations of the active substances in specified dosages on weeds. The amount of spray preparation was uniformly SOU l / ha. 4 weeks after spraying, the herbicidal efficacy was determined. The remaining weeds were harvested - separated by weeds - and their fresh weight determined. In the same way, weed in the comparison boxes that have received their ohehnnlladu. 446 928 The nterftnendc weed plant after treatment was added in advance to the weed plant in the ohehnndlude boxes and on such a lust the current herhicidal efficacy lä nvdödningen was dropped. These values were then examined in the case of product inventory using the Limpcl formula for the presence of any synergistic effects.

The compound "Pyridate" was used in the following formulation: 70 Z of active substance f, 5 ulkylarylsulfonate-polyoxyethylene-emulsifier mixture 22.5 3 solvent The compounds "Woxynil-octanoate" or "ßromoxynil-octanoate" were used as the following preparation: Active Emulsifier Mixture of aromatic hydrocarbons "L-xynil-nctanoate" (equivalent to 400 g / l 47.02% 4.38% to 100% phenyl equivalent) "L; 100 g / l 51.08 4.38% to 100% {-n ~ lekvivulentl f luxynil-Na-salt was used as an aqueous solution in- h2; luie yet g phenol equivalent / 1, Bromoxynil-Na salt likewise sw »nm fatty solution containing 35 g phenol equivalent / l.

The information regarding kg / AS / ha in the tables refers to loxynil- resp. Bromoxynil-octanoate and in the case of Oxynil-Na re n. Üronnxynil-Na to current equivalents of free phenol.

Explanation to Tables 1 to 5: II-O-β-phenyl-6-chloropyridazinyl- (4 [7-S- (n-octyl) -thiocarbonate {"flyrila: e" I il f 4-hydroxy-3,5- diiodobenzonitrile octanoate ("Ioxynyl-1-octanoate") lll = 4-hydroxy-3,5-dibromobenzonitrile-octanoate ("Bromoxynil-octane" l ll = lvxynil ~ Na-salt V = Bromoxynil-Na ~ salt om om ON mm Nm Om om No 446 928> om 0. om m «om mm om _.o. Mm om mm mm mm mm mm No> N cm mN mm Cm m. Mm mm _.o mm om om ON mm om mm No Hmm om ON Nm mm NN mm om _.o GN Nm Nm om ON Nm mß No NN NN om mN mm cm Nm om _.o om mm mm mm GN mß om om.o H Nm om Nm Nm mm mm NN mN.o O mm QUN < «: \ M <mm m wcmmomø fi mm mmhwø» nm: m: @s fl> <Qcem wEæwzNæ> E H fl oßmm 446 928 17 m + ß + æ + m + N_ + w + ~ + «_ + m + m + N + m fi øwwww fifi N ... 2 . ä å ä ä ä å å S ä »Ešssws 29 09 ä 9: 9: 09 09 09 9: 99 09 ubsssm Nå + m6 TT wï 9+ .ZTT 9+ I + E + T wsms fifi s sm Nm ss om mm om mm qæ ms sw mm pmcxmnmß å 09 3 9: 9: R, o9 09 9. G9 09 Éss fi io + m6 o + m + m + 07+ í + o ... m + mN + OT .. NT .. ß ... m fl mhmmw fifi å å ä â å ä EI om S ä Äsšwsws 2. 09 om 09 09 ä 09 09 99 G9 99 Essä NS + 26 I + E + s? m? 99+ T n + E? o: s? í + wsmswmfåw 2 3 9 3 å å ä i 2 .q å smsfmsms ä 9: å. 09 9: ä ä .G9 3 09 09 Éssi is + Ra .siss .wsss Q s <12+ Su z .o wmpw: > w mcsswæ @> <osšm ßxxwd wa wc fi nnmcø ~ äæw4æu> m H fi wßmh J .. 1.111 wvws-wvvuun-.ïïmr 18 446 928 T w + E + E + ~ + T T. E + E + E + E + T mcmhwäwo mm Nm No mm mm »W om Nm umcxmnmn 2: oE 09 oo. 2: oo. oo. oo .. oo. oo. E: »wcš fi Nä + m6 E + E + E + T w + E + w + E + T, o + o + wcw fi šw fi, .ä om 2. mo Nm wo Nm E oß mm .om Hwcvšawn å oo. 3 om oo. oo. å. 8. 3 3 oE Essä to + m6 T E + i ... E + m: E + T. E + E + E + m + wcokwïwo om mo f mo om om mm mo å No .m oåšwü fi wn om oo_ om mm mm oo. and oo, about oo- oo. wwccüm ~ .o + 2.0 E + mi. E + o + E + E + I + om + o + E + E + wcmnmww fl o i fw om m »om .å mm wo .R om om pmcmmnøn i om om mo oE oE oE om om om om» oacsw io + mïo .E x _ H zoomooo <: So + IT § ß. 4 motion> m. mšcw fi š / .o mcffwmoo ocam oEnmxwo> m H fi onnfo 446 928 19 - @ + || m1 wn T m: _: f T. mcwhwwwïq om ä. å cm .ä å å mm E mw S pwcxmnms ä on 3 3 3 2 02 ow om 2. S. ÉQEG Ná +. m6 .T @ | f ß; .T P + Tf m: || _ + n: wcwhwww fi v E Ä. .R É å mw .å mw mß .Nm mm Pscšwhms mm mm ow om om om mm om 2 mm mm poccøm Éo + mo ff '_ + .TN: w: ~ + wa N + T . f msnåwww fi ø å .ä É EQ ææ mm f 2 ow om pmcvšhwn om. om om mm mm om oc? on 2 Nm om. pmccsw ~ .o + m fi o | » Tf T .T N ... m: Nu .ï N: T Tf mcmamwwï. 3 å 02 mm .w å Nm å 2. K mm wmcšv fi mn 3 mm S om mm E ow 3 ww oß .Ww woc fi šw íc + mïc 4 x H cumma U mc \ i TCM + ff m fl fâw / fl .i V. _ s fl pøwçc , w. .Amwmo> mw: T:., s fi _> /. Jcsm fi = dnxw .. fi_ »w: M wnwh 446 928 Q! ® + m ...

N ...

NI Q ... I! o .. miwHm- fl w fifi S å .ä 8 ä 8 8 B å 8 å Énš fi wß o? ä å 2 .. ä R 2 3 E .. ä 8 »Råå Nä + m6 || _ + f i? ~ | m .. 9. T m + I .T wcmïšw fi m. 3 3 i 2 ä ä å S 2 å ä BNEEQQQ 2 om S 3 2 .. om å ä S om 8 »wššm ío + m6 m1 @ + m | N »n +« + m + _ + m: ~ | _ + mcmwmmm fi w 3 i 2 B 2. å 9 .. 3 å S å p fl šmpoß om cm oß oæ oo. Om mm om ow om 00 pwannw NQ + w ~ .o mn w: q + m + m + mn N: ~ + _: sf ~ + mcohmww fl w 2 S å 2 â â B 3 2 3 2 Éëmïrš 2 om 2 8 å ... w .ä 2 2 3 .u pïë flfl * iQ + 3.0 .._ v * H = U .__ .mn n. m <S5 + S, @; \ w <M1 mc fi æwmoa w mmnmo> cm; m: umc> < UCER v52., MÄH 0 ..) m.HH @@ fl ~

Claims (2)

Zl 446 928_ Putenïäïgv 1. An agent having a herbicidal action, characterized in that the total active ingredients contain the compound O- [B-phenyl-0-chloropyridaziny1- (4l] -S- (n-octyl) -rio- Lcnbwnate 1 mixture with the compound 4-hydroxy-3,5-diiodobenzone-11-octane® and / or 4-hydroxy-3,5-dibromobenzonitrile-octane-1 in a conversion ratio of from 1: 1, b to 1: 0.1, the amount of of the hydroxybenzonitriles are indicated in phenolequiviranes. Use of an herbicidal agent according to claim 1 for controlling weeds, characterized in that the cultures after the emergence of the plants are treated with the agent that the compound O- [β-phenyl-6-chloropyridazinyl] bi [7-S- (n-octyl thiocarbonate is given in an amount of use of 5, 5 to 1 kgfhu and the compound 4-hydroxy-3,5-diiodobenzonyl) in carbon or 4-hydroxy-3,5- dibrumhensonitrile] -octane in an application rate from 0.1 to 0.4 kg / ha.