DD201637A5 - SYNERGISTIC AGENT AND METHOD FOR SELECTIVE WEED PREVENTION - Google Patents

Abstract

An agent which comprises on the one hand a 4- (3 ', 5'-dichloropyridyl-2'-oxy) -alpha-phenoxy-propionic acid propargyl ester of the formula in which Z is oxygen or sulfur and, on the other hand, 4-amino-3-methyl-6 contain phenyl- (4H) -1,2,4-triazin-5-one or methyl-3-m-tolyl-carbamoyloxyphenylcarbamat in mixture with each other, show in sugar and Futterruebenkulturen synergistic herbicidal activity.

Description

3 1 A 3 O «AP A Ol M / 231 438/1

Synergistic agent and method for selective weed control

Area of application of the invention

The present invention relates to a synergistic agent, which contains a herbicidal active ingredient combination, which is extremely suitable for selective weed control, especially in sugar and feed beet crops. The invention also relates to a method of controlling weeds, especially in sugar and fodder beet crops using the new agent.

Currently the most common and important weeds in sugar and fodder beet crops are species of the genus Amaranthus (Foxtail). Chenopodium (goosefoot), Sinapis (mustard), panicum (millet) and certain Avena species (wild oats),

Characteristic of the known technical solutions

As excellent postemergic selective herbicides against monocotyledonous we have 4- (3 ', 5'-dichloropyridyl-2'-oxy) - <^ -phenoxypropionsäurepropargylester of formula I.

, Cl CH_

λ A / * * \ I 3

Cl · "\\ -0-. * -0-CH-CO-Z-CH ₀ -C ^ CH (I). \ / \ / ²

where Z is oxygen or sulfur.

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The two compounds of the formula I which is 4- (3 ', 5'-dichloropyridyl-2'-oxy) - oL -phenoxyp ropionsäu rep roρa rgylester (Ia) and 4- (3', 5'-dichloropyridyl-2 ' -oxy ) -cL -phenoxypropionthiolic acid propargyl ester (Ib), their preparation and use as selective herbicides are described in European Patent Publication No. 3114

Dicotyledonous weeds are often successful with 4 ~ amino-3-methyl-6-phenyl 4HL £ ~ l ,, 2 _f .4 ~ t ~ 5 ~ riazinetrione one (metamitron) of the formula Ha

or with methyl S-m-tolyicarbamoyloxyphenylcarbamate (Phenmedipham) of the formula Hb

I Il .11 ^ό (Hb)

in postemergent use fights »

Metamitron and its herbicidal activity has been found, for example, in the 3rd ,, Int. Meeting of Selective Weed Control described in Beet CropSj, Paris, 1975, ..

3 1 4 3 8 I 9.11.1981

AP A Ol N / 231 438/1 - 2a - 59 354/12

About phenmedipharn and its herbicidal properties is described in Abstr. 5th Int. Congr, Pl. Prot ,, Vienna, 1967 ,. P. 433 reports.

Object of the invention

The aim of the invention is das.Bereit position new herbicides with increased effectiveness. which are suitable, the most important and z. Z * to selectively destroy the most common weeds in feed and sugar beet crops.

Explanation of the essence of the invention

The invention has for its object to use for weed control mixtures of certain known herbicides and thereby to achieve a biological effect that is stronger than the additive effect of the individual components.

It has now surprisingly been found that a quantitatively variable within certain limits combination of the two classes of active agents 1 and Il unfolds a synergistic effect that is able to combat the majority of all important weeds in sugar and fodder beet crops, without damaging these crops. The main weeds of the crops, such as the dicotyledon gattuna Amaranthus, Chenopodium and Sinapis, and the monocotyledon genera Panicum and Avena, are selectively destroyed in the accumulated sugar and fodder beet crops. »

It is surprising, that the combination of an active ingredient of the formula I with an active ingredient of the formula II not only a principle

\ "4 V ^ W *

The composition according to the invention with the new combination of active ingredients contains, in addition to the active substances mentioned, suitable carriers and Xodors other additives. These may be solid or liquid and correspond to the usual in the formulation art materials such. natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. Emulsion concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, also encapsulates in e.g. polymeric substances. The application methods such as spraying, misting, dusting, scattering or pouring. Like the type of means, they are chosen according to the desired goals and the given circumstances.

The formulations, i. Compositions containing the active substance of the formula I and, if desired, a solid or liquid additive, are prepared in a known manner, for example by intimately mixing and / or grinding the active compounds with extenders, such as, for example, with solvents, solid carriers, and optionally surface-active compounds (surfactants).

Suitable solvents may be: Aromatic hydrocarbons, preferably fractions C to C ₁₀ , such as xylene mixtures or substituted naphthalenes, phthalic acid esters such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, Aethylenglykolmonomethyl- or -äthyläther, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, and optionally epoxidized vegetable oils such as epoxidized coconut oil or soybean oil; or water.

O! 4 <? O I

As solid carriers, e.g. for detergents and dispersible powders, ground natural minerals are generally used, such as calcite, talc, kaolin, montmorillonite or attapulgite. To improve the physical properties, it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. As granular, adsorptive granule supports, porous types, such as e.g. Pumice, broken brick, sepiolite or 3-tonon, as non-sorptive support materials e.g. Calcite or sand>: in question. In addition, a variety of pre-granulated materials of inorganic or organic nature, in particular dolomite or crushed plant residues can be used.

As surface-active compounds are nonionic ,. cationic and / or anionic surfactants having good emulsifying, dispersing and wetting properties. Surfactants are also surfactant nits to understand.

Suitable anionic surfactants may be both so-called water-soluble soaps and water-soluble synthetic surface-active compounds.

Suitable soaps are the alkali, alkaline earth or optionally substituted ammonium salts of higher fatty acids are (C _1n to C _72), ^w ^ ^e eg the sodium or potassium salts of. OeI- or stearic acid, or of natural fatty acid mixtures, which may be obtained, for example, from coconut or tallow oil, called. Furthermore, the fatty acid methyl taurine salts should also be mentioned.

More often, however, so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates.

The fatty sulfonates or sulfates are generally as alkali metal, alkaline earth metal or optionally substituted ammonium salts

O- I 4 O O 1

before and have an alkyl radical having 8 to 22 carbon atoms, wherein alkyl also includes the alkyl moiety of acyl radicals, e.g. the Nacdar Ca salt of lignosulfonic acid, of the dodecylsulfuric acid ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids. This subheading also covers the salts of sulfuric acid esters and sulfonic acids of fatty alcohol / ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2-sulfonic acid groups and a 8-22 fatty acid residue. C-Atom alkylarylsulfonates are 2.3. the Na-j Ca or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or a naphthalenesulfonic acid-formaldehyde condensation product.

Furthermore, corresponding phosphates, e.g. Salts of the phosphoric acid ester of a p-nonylphenol (4-14) -ethylene oxide adduct in question.

Suitable nonionic surfactants are, in the first place, polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, 3 to 30 glyceal ether groups and 8 to. 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols may contain.

Further suitable nonionic surfactants are the water-soluble, 20 to. -250 ethylene glycol ether groups and 10 to 100 propylene glycol. Polyäthylenoxidaddukte containing ether groups to'Polypropylenglykol, Aethylendiaminopolypropylenglykol and alkylpolypropylene glycol having 1 to 10 carbon atoms in the alkyl chain. The compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Examples of nonionic surfactants are nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene / polyethylene oxide adducts, tributylphenoxypolyethoxyethane1, polyethylene glycol and octyl

J 1 4 O O I

- 7 phenoxypolyäthoxyäthanol mentioned.

Also suitable are fatty acid esters of polyoxyethylene sorbitan, such as the polyoxyethylene tributyl tri-oleate.

The cationic surfactants are, above all, quaternary ammonium salts which contain at least one alkyl radical having 8 to 22 carbon atoms as N-substituent and lower, optionally halogenated alkyl, benzyl or lower hydroxyalkyl radicals as further substituents are preferably in the form of halides, methylsulfates or ethylsulfates, for example Stearyltrimethylammbniumchlorid or Benzyldi (2-chloroethyl) ethylammonium bromide.

The surfactants commonly used in formulation technology are i.a. described in the following publications:

"McCutcheon's Detergents and Emuslifiers Annual" MC Publishing Corp., Ringwood, New Jersey, 1979.

Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc. New York, 1964.

The active ingredient content in marketable agents is between 0.1 to 95 weight percent, preferably 1 to 80 weight percent.

In particular, preferred formulations are composed as follows: (% = weight percent)

solutions

, Active ingredient: 5 to 95% ,. preferably 10 to 80%

Solvent: 95 to 5% ,. preferably 90 to 0% surfactant :. 1 to 30% ,. preferably 2 to. 20%.

L J! 4 OO I

Smulgable concentrates

Active ingredient: Surfactant: Liquid carrier:

to 50%, preferably 10 to 40% 5 to 40%, preferably 10 to. 20% to 95%, preferably 40 to 80%.

dusts

Active ingredient:

solid carrier:

Q, 5 "to 10%, preferably Z to 8% 99.5 to 90%, preferably 98 to 92%.

Suspension Concentrates Active Ingredient: Water: Surfactant:

5 to 75%, preferably 10 to 50% to 25%, preferably 90 to 30% 1 to 40%, preferably 2 to 30%,

Wettable powders Active ingredient:

Surfactant: solid carrier:

5 to 90%, preferably 10 to 80% and

in particular 20 to 60% 0.5 to. 20% ,. preferably 1 to 15% 5 to 90%, preferably 30 to 70%.

granules

Active ingredient:

solid carrier:

0.5 to 30%, preferably 3 to 15% 99.5 to 70%, preferably 97 to 85%.

While more concentrated products are preferred as the commercial product, the end user will typically use diluted products. The forms of application may be diluted to as low as 0.001% of active ingredient.

The described inventive compositions can be mixed with other biocidal agents or agents. Thus, the new Mittelausser the said compounds of the general formula I and the formula II, for. Insecticides, fungicides, bactericides, fungistatics, bacteriostats or nematicides to broaden the efficacy

9.11.1981 AP A Ol N / 231 438/1 - 9 - 59 354/12

Spectrum included ».

A synergistic effect is always present in herbicides if the herbicidal action of the active ingredient combination I + II is greater than the sum of the effect of the individually applied active ingredients *

The expected plant growth E for a given combination of two herbicides can be calculated (see * Colby, S, R., "Calculating synergistic and antagonistic response of herbicidal combinations", Weeds 15, pages 20-22, 1967) as follows:

r- X. Y

100th

Where:

X = percent growth (compared to untreated plants) when treated with a herbicide I with ρ kg application rate per hectare *

Y = percent growth in treatment with a herbicide II with q kg application rate per hectare,

E = Expected growth in percent to the control plants after treatment with herbicide mixture I + II at an application rate of ρ + q kg of active ingredient per hectare

If the actually observed value is lower than the expected value E ,, then synergism is present.

Working Example

The invention will be described below. some examples explained.

JI II 8 I

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The synergistic effect of the combinations of agents I and II is demonstrated in the first of the following examples

Example 1:

The test plants are sown in plastic containers containing 30 1 sterilized garden soil * in the greenhouse. After emergence, the plants are sprayed in the 2- to 3-leaf stage with an aqueous dispersion of the active ingredient combination. The application rate of dispersion

2 _

wears 50 ml per m, after 15 days at temperatures of

17 to 23 C, a relative humidity of 50 to 70 % and

Ö Q I

- 10 -

Daily irrigation of the container is the evaluation.

The degree of damage of the plants is assessed linearly according to the following scale: 1: plants, died 5: medium effect 9: normal state.

For different mixing ratios and total active ingredient

the following results are obtained:

a) Table 1: Tolerance and activity of 4- (3 ', 5 ^T-2 -Dichlorpyridyl ^r oxy) -a-pheno: xypropionsäurepropargy ester (verb Ia) and Metamitron (verb Ha) and mixtures thereof with postemergence he!.. Application:

Metamitron (verb Ha) kg AS / ha 1.0 0.5 12:25 0 Connection. Ia. kg. AS ^ ia. , ... m vT! ; n • o d d to u-i CN o · d d m iN o σ 0.5 0.25 Sugar beet 'Kawemono' Turnip 'Corona' Panicum crus-galli Avena fatua Amaranthus retroflexus Chenopodium album Sinapis arvensis 9 9 9 9 9 9 9 11 2 11 2 11 6 11 9 4 3 9 9 9 9 9 9 9 11 91 1 6 '1 1 9 2 2 9 9 9 9 9 9 9 9 1 9 1 9 3 9 3 9 9 9 9 9 9 1 1 1 1 9 9 9 9 9 9

If the values calculated according to the method Colby for additive effect are compared with the results from Table 1, then it is recognized. one can see that the observed growth rates in Amaranthus retr., Chenopodium alb. and Sinapis arvensis are smaller than the calculated effects. This is. demonstrated the synergistic effect of the mixture of 4- (3 ', 5'-dichloropyridyl-2'-oxy) -α-phenoxypropionic acid propargyl ester with Metamitron (see Table 2).

S ar

u "

tr o

αϊ η M <J (U O rt I tsi measured _< : <J ' Η · pi (D 0 O rt B P value (D (D £ 3 It) H jj H- ii O (D 0 η • i (D rt IU η fu H O expected CT Ό O 0 Rüb (D value * Η · Ό thu fat O (D to odi (A ti O ^J measured value M M H (U W F ^ to OQ Φ <] H • O (D (D rt O expected PT * PI* 0 (A H O value OQ (W Η · tr * O _t _ _A measured (α O O value > 1-· expected fu fu H- ¹ * - * O O 0OT value I- ¹ O 0OT measured Ui Ι-ι I- ¹ N) t " H- H- ¹ value .00 NJ O O expected H- ¹ k- ¹ H- ¹ I · value O NJ Ui 8th O O measured O Λ t- ¹ value NJ O O O O Ui ι- · NJ I- ¹ I- ¹ K- ¹ expected value NJ O O I- ¹ * - M M O O O O tr- ⁴ NJ r * H-* O t * NJ »- * I- ¹ O O O O Ui O O O O H ¹ O O O O O Ui t- ¹ _M O I O H- "NJ O O 100 years O H-" I-> h- ¹ NJ Ui   ο, ο O O 0OT I- ¹ NJ Ui O ^; O NJ Ui O O 100 V · ivj ivj 100 100 Ui Ui

(D NJ

C C

L J 1 4 OO I

- 12 -

Phenmedipham (Verb.lib) kg AS / ha 1.0 0.5 12:25 0 Verbindung.Ia.kg.AS/ha. LH U-I CN • o do , u-i u-l es) ο d α m CN o d 0.5 0.25 Sugar beet 'Kawemono' Turnip 'Corona' Panicum crus-galli Avena fatua Amaranthus retroflexus Chenopodium album Siaapis arvensis 9 9 9 9 9 9 2 1 1 91 1 9 6 6 3 j 3 ¹ 2 2 1 9 9 9 9 9 9 3 1 1 9 11 9 7 9 4 ·· J 3 7 2 4 9 9 9 9 3 '1 9 1 9 9 9 3 9 7 9 9 9 9 1 1 1 1 9 9 9 9 9 9

If the values calculated according to Colby for additive effect are compared with the results from Table 3, it can be seen that the growth values in Amaranthus retr., Chenopodium aIb. and Sinapis are less aryan than the calculated effects. This proves the synergistic effect of the mixture of 4- {3 ', 5'-dichloropyridyl-2' '- oxy) -p-phenoxypropionic acid propargyl ester with phenmedipham (see Table 4).

Table 4 ; Values Calculated by Method Colby to Demonstrate Synergism between 4- (3 ', 5'-Dichloropyridyl-2'-oxy) -a-phenoxypropionic acid Propargy! Ester' (Compound Ia) and Phenmedipham (Compound Hb)

ΙΛ H- O Ϊ % PI P TM P (D bf (D Ö rt η H rt | u £ j H 0 H- rt K " CT * fu ti O | u M η W (D H- H- (A O CJ rt Wed. ^ j 3 ^: E * rt p: ti: rj H (U H- P rt η tr he O | 1 ω P (U H C (D OQ 0 (D ^ ₁ I 1-1 , - ^ 0 P) (D OQ Ω he (η H ⁴ rt O tt> H- he H I- ¹ rl *: (A O H- O OQ he Wed H ⁴ 0 IU 8th * (D 0 H O H -J SL (A tu OQ nl VO Iu VO OA N) t- ⁴ VO VO 0 ^ I- ⁴ I- " I- ¹ VO VO 0.5 O OQ H ⁴ t-> VO VO VO VO 12:25 VO VO CN ⁴ VO VO 0 00 i-i l · - ⁴ VO VO 0.5 O H- ¹ H ⁴ ln - J nl NJ VO vo VO vo 12:25 VO VO VO VO vo 0 O I- ¹ I- ⁴ N) VO N) NJ I · I- ⁴ VO VO 12:25 ln VO VO VO VO VO 0.5 I- " I- ¹ O VO VO VO VO VO 12:25

OQ (D.

rt

(D

ft

OQ

He does

Ό 0 B ο O (0 P. ⁴ ft Π) (D i mead ί ran

rt H O CJ

He

H in

(D H

H-

(A

(W (D

3 I

H-rt (u: rt

Sin Che I Ave B ο Fut I CJ Zuc measured <i iD (D  ο O H [u S H · O orona ' rt (O O (D value α * it he H- (A (U ti O P. Hg rt B * IA fatua i O (IQ rrübe rrübe I-h tu He (D 0 Ui ret expected OQ OQ H- tr H value il> fr * (A O I I O O measured value di (U ι V- * N) α \ O N) t- ⁴ H ⁴ I- ¹ O H- ⁴ O O expected Ui _ _ O O value I- ⁴ NJ N) Ln 8th h- ⁴ t- ⁴ ; 100 measured 100 value ο I- ⁴ nl expected O a * ,. N) H ⁴ O O value Ui Η · O O t- ⁴ N) N) U) Q O H-· H ⁴ H- ¹ O O measured O O I- ¹ value Κ- ⁴ N) N) Ln ul h- ⁴ K- ⁴ I- ⁴ O expected O h- ⁴ O O value Ui LO O O measured value ul -J O t- ⁴ J- ⁴ »- expected O O value Ui t- ¹ 8th t ' N) Ln O ρ I- ⁴ j> O O O 1-' O O 100 Ui UJ LJ O O J- ⁴ 100 t- 'O a N) Ui 100 I · O O O O O H- ⁴ O O O Ui N) Ui O O O

Lo I

in η te- i> pl O O £ 1 P η I measured j ι <t < H- tr B <i H- H rt J * value expected i ID (D ti (D h> (C η O rt (D (D H value > t tu Ρ " H pl pl (D H B ä expected measured! he he ti H- 0 β | u IU D pl he value Value j a ta ο rt hl η O (D ! i H P- tr tu * OQ tr  * measured J J M (U H- pi rt » (D value expected; Cf tu 3 (A 0 | u value (D expected ir * tA (D rt O I- 'O value OQ OQ H- he HJ O O measured Ui value I ι- * H-" * - * expected | u UJ O O 8th value "-J H- ¹ H- ¹ O H- ¹ HJ HJ measured ul 8th 8th value O O ON K) H- ¹ KJ H- ¹ HJ H- ¹ HJ O O O O O OO Η- · HJ H-" H- ¹ HJ O O O O O KJ Η- · HJ cn 8th ON K) H- ¹ Kj ^ H ^ O O 8th 00 t- ¹ H-* Η- · HJ HJ O I- ¹ 8th O O Ui O O O O kj l · - * O Ui ) -I 8th O O ul KJ K) ¹ HJ HJ O HJ O O 8th K)! I- ' H-* Ln ^; O O O O kj H-* _ _ H- ¹ HJ O HJ O 8th H ¹ K) H- 'K) H- ¹ O O o; O •! K>! Ki H- ¹ Ui Ui O ε h- ¹ O O O O H- ¹

rt OQ tr ti I H- cn P- Λ φ tr H- (D H- O ta H- (u H H H- (A 1-* (B rt S Ui rt P- O ti HJ (A * ^? to (D Φ (D (D T P- H- pi tA (A pl  i (D (A P- H- P- Cl pr H § H- ro rt P- H- Φ xe-p see (D syn Φ P? Φ H η η 4 G φ {j r> O pr tr H (A pr • d H I OQ H- tA ία η ft) »j s; ti Η · (A rt φ 0 · rt he 11 o ul ci (A Ε " (D t ι ti rt tJ · HJ u \ HJ η ^ * I- ¹ H- r ^ la Φ H- jj rt ο (THERE ° i (D m O η tr PJ H rt he rt cn 0 Φ ro rt Φ (D Ui η rt (D pj For H O • tr pi I H- Hi (A he P) A ^^ ^ ö he D Hi H- Φ (S A H <^ H- (A (D Ö H- (A rt (D η (D lu: P. < ' H 0 ^ urepr rt spring- Yes Φ ll Η ** O rechn O P- P) fu he H (D ^r d Φ Is di H Hurry Η G pyrid rt ti r mis (D anthu Ui Ν 0 (D ο (a ί P- t-i £ 3 * ^ he Φ N Φ OQ t K3 (D (THERE B H Φ H ID rt (D. rt OQ Φ r \ it OQ t ..ι about rt i * (D I J pr H | - H- η (D H- H O PI φ - pr η ρΤ rt rt η Φ φ H I H- • P- (D. pl rt O rt I pl φ P pr PJ U) ac; Pl O (A ./-""N (D O mead H' * 0 O y I fu H O (D O H- rt Ui ί P. ork He (A H £ (M ium φ Per (D O H- s. nnt H H (A n- be chi alb H- Syn I O ο • • on- (D H rt on, pyri and P-

- 15 -

d) TABLE 7 Tolerance and activity of 4- (3 ' , 5'-dichloropyridyl-2'-oxy) -α-phenos-7-propioathiol acid propargyl ester (Verb.IB) and Phenmedipham (Comp. lib) and their mixtures in postemergence Application.

Phenmediohan (verb.lib) ^ks AS / ha 1.0 0.5 12:25 O Compound Ib kg AS / Tia u-i o d U-I UI SN O O O U-, O O 0.5 0.25 Sugar Beet 'Xaweaono' Fodder Beet 'Corona' Panicum crus-galli Avena fatua. Amaranthus ratroflexus Chenopodium album Sinapis arvensis 9 9 9 9 9 9 2 1 1 9 1 1 9 7 8 '3 2 2 2 2 2 9 9 9 9 9 9 3 1 1 9 11 9 7 9 4 2 2 7 3 4 9 9 9 9 8 1 9 1 9 - 9 9 9 9 9 9 1 1 1 1 9 9 9 9 9 9

If the values calculated according to Colby for additive effect are compared with the results from Table 7, it can be seen that the growth values in Amaranthus retr, Chenopodium alb. and Sinapis arvensis are smaller than the calculated effects. Thus, the synergistic effect of the mixture of 4- (3 ', 5'-dichloropyridyl-2'-oxy) -a-phenoxy-propionthiolsäurepropargy! Ester with phenmedipham proved (see Table 8).

Table 8 : Values calculated by Method Colby indicate the synergism between 4- (3 ^f, 5 ^f -dichloropyridyl-2- ^f -oxy) -c-phenoxy-propionthiolic acid propargyl ester (Comp. Ib) and Phenmedipham (Comp. Lib).

- 16 -

Verb. Lib. kg AS / ha 0.5 1.0 12:25 expected value 0th 0.5 5 0th 25 0th 25 expected value Verb. I b kg AS / ha. measured value measured value measured value expected value measured value expected value 0th 25 expected value 100 measured value 100 sugar beet 100 100 100 100 100 100 'Kavemono' 100 100 100 100 mangel 100 100 1 100 100 100 100 1 'Corona' r-l 100 r-l 1 1 1 1 1 100 r-l anicum, e.g. 1 1 1 100 1 1 1 r-l , ι 100 Avena fatua 25 1 87 _y 25 75 100 100 100 r-l 100 Amaranthus retr. 12. 100 12 12 12 37 25 37 100 100 Chenopodium alb. 12 25 12 25 75 37 75 37 Sinapis arvensis 12 100

Foraulierungsbeispiele

Example 2: a) b) O). the d) 10% 2Q% 5% 30% 10%., 40% 15% 30% 5% 5% 5% 5% Fonnulierungsbeispiele for synergistic mixtures of active ingredients 3% - 3% - Formulas I and II (% by weight) - 6% _ 6% a) spray powder Active ingredient Ia or Ib Active ingredient Ha or Hb Na ligninsulfonate Na lauryl sulfate iTa-diisobutylnaphthalenesulfonate

Octylphenolpolyethylene glycol ether 7-8 mol AbO)

Highly dispersed silica kaolin

- 2% - 2% 5% , 27% 5% , 27% 67% 67%

- 17 -

The active substance mixture is mixed well with the additives and ground well in a suitable mill. This gives spray powders which can be diluted with water to: suspensions of any desired concentration.

b) emulsion concentrate active ingredient Ia or Ib active ingredient Ha or lib

Octylphenolpolyethylene glycol ether (4-5 moles of AeO) Ca-dodecylbenzenesulfonate Ricinusölpolyglykoläther (36 moles of AeO) cyclohexanone xylene mixture

a) b) c) 5% 5% 12% 5% , 20% 13% 3% 3% 3% 3% 3% 2% 4% 4% 4% 30% 30% 31% 50% 35% 35%

From these concentrates, emulsions of any desired concentration can be prepared by dilution with water.

c) dusts

Active ingredient Ia or Ib active ingredient Ha or Hb talcum kaolin

a) b) c) d)

Currently: 4% 2% 4%

• 3% 4% 4% 8%

95% - 94%

92% - 88%

Ready-to-use dusts are obtained by mixing the active ingredient mixture with the carrier and grinding on a suitable mill.

d) extruder granules active ingredient Ia or Ib active ingredient Ha or Hb sodium lignin sulphonate carboxymethyl cellulose kaolin

a) b) c) 5% 3% 5% 5% 7% 15% '2%. , 2% 2% 1% 1% 1% 87% 87% 77%

- 18 -

The active substance mixture is mixed with the additives, ground and moistened with water. This mixture is extruded and then dried in a stream of air.

e) serving granules a> b) Active ingredient Ia or Ib 1.5% 3% Active ingredient Ha or Hb 1.5% 5% Polyethylene glycol (MG 200) 3% 3% kaolin 94% 89%

The finely ground active substance mixture is applied uniformly in a mixer to the kaolin moistened with polyethylene glycol. · In this way you get dust-free coating granules.

f) · suspension concentrate active ingredient Ia or Ib.

 Active ingredient Ha or Hb ethylene glycol

Nonylphenolpolyethylene glycol ether (15 moles of AeO)

Na ligninsulfonate

Carboxymethylcellulose 37% aqueous formaldehyde solution

Silicone oil in the form of a 75% aqueous emulsion

water

The finely ground active substance mixture is intimately mixed with the additives. This gives a suspension concentrate, from which by dilution with water suspensions of any desired. Concentration can be made.

a) b) 20% 20% 20% 40% io% 10% 6% 6% 10% 10% 1% 1% 0.2% 0.2% 0.8% 0.8% 32% 12%

Claims (3)

1. Synergistic agent for selective weed control, characterized in that, in addition to carrier and / or other additives as an effective component, on the one hand, a 4- (3 ', 5'-dichloropyridyl-2'-oxy) -o-phenoxypropionsäurepropargylester of the formula I * _ * '. , · - _t CH ₃ -Y- Y-O-C-CH-CO-Z-CH-C = CH (I), W ν- wherein Z is oxygen or sulfur, and on the other hand, 4-amino-3-methyl-6-phenyl - / "4Hj7-l, 2,4-t riazin-5-one (lla) or methyl-3-m-tolyl-carbamoyloxyphenylcarbamat (Hb) contains. 2, Composition according to item 1, characterized in that in said agent, the component (II) over the component (I) in approximately the same weight ratio or in excess is present. 3, agent according to item 2, characterized in that the weight ratio between component (I) and component (II) is 1: 1 to 1: 4, preferably 1: 1 to 1: 2. 4, A method for selective weed control in sugar and fodder beet crops, characterized by treating weed sugar or feed beet crops postemergence with an effective amount of an agent according to item 1. 9,11.1981 AP A 01 N / 231 438/1 - 20 - 59 354/12 5. The method according to item 4, characterized in that one sugar and feed beet crops, which as weeds dicotyledons of the genus Chenopodium, Amaranthus and Sinapis and Monocotyledon unglas of the genus Panicum-. and Avena, treated with the said agent. 5, process according to the items 4 and 5, characterized in that the sugar and feed beet crops are treated with said agent in an amount of 0.2 to 4 kg, preferably 0 to 5 to 3 kg of total active substance per hectare correspond. 7. Use of an effective amount of an agent according to item 1, characterized in that it is used for postemergent weed control in sugar and feed beet crops.