DE1642367A1 - Herbicides - Google Patents

Description

DR. WG PFEIFFER
PATE NTAN WALTE
MONCHEM 23
UNGEtIKSTKASSI ZS

75 800

Velaiool Chemical Corporation, Chicago _t Illinois, V. St. A. Herbicides

The invention relates to new herbicidal agents for the Control a wide range of weeds are effective. "

Many organic and inorganic substances have been proposed and used for weed control. Although some of these substances are partially successful, but there is more to apfen he k the Probleia.die extensive Anaahl kinds of unwanted Pflaneenwachstums. The W "her vogeaehlagenen substances are effective for Beküapfung certain weeds, but · wurd not have a compound or composition found, along with 11 cha types of weeds effectively belcämpfen ver-MQG, without his zn excessively toxic and unterechiedcloa a σ * ο hl . desired as undesirable plant growth

105811/2095

destroy.

In particular, compounds have effective herbicidal activity following groups I bia VH against certain weed species all proven to be effective, but are relatively ineffective compared to others "

Group I - compounds of the general formula:

wherein X ₁ , Xg _f X », X * and Xc independently of one another halogen atoms, in particular chlorine and bromine, lower alkyl radicals, in particular methyl, ethyl, propyl, sec-butyl and sec-amyl, lower alkoxy radicals, in particular methoxy and ethoxy, Nitro groups, amino groups, phenyl radicals or hydrogen atoms, with the proviso that at most 2 of the radicals X ₁ , X ₂ PX », Xj and Xc are hydrogen atoms, and Y is -OH or -COOH, in which η is an integer

109821/2095

8AD OFIiGiNAL

- 3 tone 1 to 3 1st, as well as their Salse ,. Amides and esters.

Group II - carbamates and thiocarbamates Group III - s-triasins, ureas, Benson! Trile,

2 _r 6-dihalo-4-cyanophenylQQter lower aliphatic acids and thiobeneamides "

Group IT - compounds of the formula:

Cl CEl

CSR ₂

Cl

wherein R _{2 is} a lower alkyl radical which preferably contains 1 to 3 carbon atoms;

Group V - compounds of the formula: ™

Cl Cl O

C-O-R »·

egg egg '*:

109821/2095

164236?

where B "" Inen denotes a lower alkyl radical; Group YI - 3 »4-dichloropropionanlide
Group VII - 4-amino-3,5,6-fcriohlorpiooline acid.

For example, the compounds of Group I have generally been found to be effective in controlling certain weeds, for Example dock, mustard, foxtail, curmudgeon, rush and The like have been shown, but are generally unable to destroy other weeds. Hit various of these Herbicides have been tried to control the entire broad SpektBums carried out by weeds in quantities suitable for Cultivated plants are harmless, but the attempts failed and the weeds continued to grow and thereby lead to considerable economic losses as a result of competition with cultivated plants, to harvesting difficulties, low yields and the like.

The invention aims at herbicidal agents for control a wide range of weeds that can be applied to crops in kengen that co-exist with the crops are compatible.

109821/2095

6AD ORIGINAL

The invention relates in particular to herbicidal agents, the • a first compound of the general formula

U)

in which Λ hydrogen, chlorine, substituted lower alkyl groups or unsubstituted lower alkeny groups; D hydrogen "halogen", unaubatitized alkyl groups or uneubatituated lower alkenyl groups and S hydrogen or chlorine "with the hate that at most one of the radicals A and D signifies hydrogen, A only signifies chlorine if D signifies chlorine and £ signifies chlorine only if A and D both represent chlorine, R * hydrogen or an alkyl group _f . R denotes an alkyl group and Z denotes an unsubstituted alkylene group it 1 to 4 carbon atoms., And the alkali metal salts of those compounds in which R * denotes hydrogen (hereinafter referred to as group A), and at least one other compound of the groups I to mentioned above VII included.

109821/2095

The herbicidal agents according to the invention contain the general combinations of two compounds, however, more than 2 compounds can in general within the scope of the invention and / or an inert carrier can be contained in the agents according to the invention.

The invention also relates to a method of destruction Tone unwanted plants, after which these plants with one herbicidal agents as defined above in a slope in Ee-

stirred for the plant ?! harmful is.

Surprisingly, it has now been found that by using combinations of a first compound from group (A) with one or more compounds from groups I to VII herbicidal agents are obtained which are effective for controlling a broad spectrum of weeds and provide results with separate compositions of the individual herbicides at comparable amounts are not achievable.

For example, the control of weeds in crop plants often sets in more quickly and yet the combinations have a remaining herbicidal activity over a longer period of time than the individual herbicidal components in equivalent amounts. Furthermore, these combi -

109821/2095

BATH ORIGINAL

*

- 7 nationeη Surprisingly well tolerated by cultivated plants.

The following are examples of compounds of the group Λ called for use as components in the invention Compositions or agents are suitable

N-methoxy-2-methyl-4-chlorophenoxyacetamia H-methoxy-H-methyl-2-methyl-4-chlorophenoxyacetamide H-methoxy-2 _t 4-dichlorophenoxyaeetaaid H ^il ethoxy-N-N-ethyl-2,4-dichlorphenoxyacetamid I-methoxy-2 _v 4 »5-trichlorophenoxyacetamide H-Kethoxy-H-Biethyl-2,4,5-trichlorophenoxy acetamide

H-IIethoxy-4-chlorophenoxyacetamide H-methoxy-4-broaphenoxyacetamide

H-methoxy-ir-methyl-4-chlorophenoxyacetamide N-methoxy-K-methyl-> 4-bromophenoxyacetamide o- (N-M «thoxy-H-methyl-2-methy1-4-chlorophenoxy) propionamide

H-ethoxy-2-methyl-4-chlorophenoxyacetamide lί-ethoxy-H-methyl-2-methyl-4-chlorophenoxyacetamide N-ethoxy ^^ - dichlorophenoxyacetamide N-ethoxy-N-methyl-2,4 ~ diehlo: rphenoxy acetamide N «ethoxy-2,4,5-trichlorophenoxyacetamide Ä ^ e ¹ ! , 5-trichlorophenoxyacetanide

109821 / 209S

: I ^ Xthoxy-li-iiethyl-4-chlorophenoxyacetaniid

H-methoxy ~ 2-methylphenoxyacetamide N-methoxy-N-methyl-2 "inethylphenoxyacetamide H-methoxy-4-ethylphenoxyacetamide N-methoxy-methylphenoxyacetamide NM« thoxy-2,4 ~ dimethylphenoxyacetamide F-methoxy »H-methyl -2 _t 4''dimethylphenoxyacetamide N-methoxy-N-methyl-2- äthylphenoxyacetomid H-HethLOsy-H-Bethyl-2-isopropylphenoxyacetamide N-isopropoxy - ^ - methylphenoxyacetamide and lf-methoxy - W-nethyl-2-ally " ! phenoxyacetamide

The alkali metal salts of those compounds from group A in which R * in the formula «1 (Λ) denotes hydrogen are particularly advantageous in the agents according to the invention, since they are soluble in water.

Examples of suitable alkali metal salts are: the potassium salt τοπ H ~ methoxy-2-methyl-4-chlorophenoxyacetanide, the sodium salt τοπ N-ithoxy-2-methyl-4-chlorophenoxyacetamide, the potassium salt clay N-methoxy ^^ - dichlorophenoxyncetaraide, the colium salt clay N-methoxy-4-chlorophenoxyacetamide, fiae N-ethoxy-2 _t 4-dichlorophenoxyacetanide _{f the} colium salt of N-methoxy-2 _f 4-diinethyl-phenoxyacetamide and the like.

109821/2095

BATH ORIGINAL

Exemplary for the Hsrfeiciden τοη Srapp® X * §% ® see sur V * rwenäuufi i »Combination with the compounds of irüpps (A) all components of the arfindnsigsg @ iaäSsn agents are;

2,3 f6 - ^? Iöhlorbeaaoesäure, 2 _β 3 «5« 6-2βtraohlarleasooeäiire, 2 " Msth © xy« »3 _f 6 ~ ätchlor ^ Gago @ säur @ ₉ 2» M @ thosf »3g5s6 - = 'trieh

Qsäiire "t ° -Kethox3f-" 3 "-ni'Sff0" = -5 ' ^: -etelö2' ^ Qßs @ © Bä "i ^> e _t 2,4

5rie

I flex

SS ₄ χ «clQßQS s £ q iiüiBi Ki * s. feia mi S! © lalQaiatef

old

LzMc Jini 'ii% [Yes

isd] Ssalsg Clei *

eii © * lky

isiaä aie ülfearw

fe 5! Τ0ΙΪ

iac

miü

^. ^? ü1-3 sii 10

ileFe? g 3ο \; ο? ί ₅ i

- ίο -

la 4 · η · η 41 · leaving a group a converted alkyl group « «It is 1 to 10 carbon atoms.

For the preparation the compounds of group are often used in the form of their alkali metal salts, amine salts and AlamonluBSslie and ia sail of the acid in the form of their amides and ethers * because thee Ssl ^ e * aöicie and esters in general loalie & er slo ate ¥ erbindttngen in For-a their acids are = piping Salsa, Aeiäg and Esters generally have an activity _P di © üen @ ntsg ^ eGkien50i! S £ Liira? I wJqt Phenolen SquiTclent is " Examples of (suitable Älkolimetallsslse, AmmoniMSiealze _f Aaiiieolses Amid3?; Ai ester, the bti des? 3uba? Si-? Uag the hsrbieldsn means ascfct" Sisae? TteSinStins

EÄPs 5, hat

Hetticisy «?: δ-ϋί

10SS21 / 20S5 -

BATH ORIGINAL

- ti -

2,4- <iinitro-6- »to-butylpheno * yd,
butylphenoxide, Aa * onium ~ 2,4-dinitro-6-ββο -butylphenoxide, £ thanolaein-2,4-dinitro-6-eec.-butylphenoxide _β IeopropanolaBin-2,4-dinitro-6-eec.-butylphenoxide, Colium 2,4-dinitro-6 ~ aec.-aaylphenoxxdp Iatriu «-2,4- <3ini-bro-6-eeo.-aaylphenoxide, AaaonLua-2,4-dinitro-6-aec.-anylphenoxide _t Ä .thanolemin-2,4-diuitro ~ 6-aecaaylphenoxide, Ieopropenol-a ^ -dinitro-e-eec.-amylphinoxide and

dtrglaiohan. *

Baiapiel "for the harbieid wirlceamen carbamates and Thioearbaaata ▼ on group II, dlt for the use in the agents according to the invention Tortallhaft aiad, alndt Ieopropyl-N-phenylcarbaaat, Ieopropjl-H- (3-ohlophenyl) oarbaaiat, methyl 4-dichlorpbeuyl) oarb "Ba fc _t 4-Ohlor-2-butiny1-1- (3-chlorpheayl) oarbanat _v 2,6-di-tert-butyl-p-tolyleethyloarbaeat; 2-chloroallyl-dittthyldithioearbaaet, ■ atriua-H-Qethyldithiocerbaaat, Xtnyl-H _t H-dir n-propylthioloerbeeat, n-propyl-di-n-propylthiolcarbanate, 2,3-di-chloroallyl-I _t I-diieopropatylthioloarbeaate n-butylthiolcarbasat and propyl-ethyl-n-butylthiolcarbasat "

the herbioid virlcaaaen e-Triaeine, Urnatoffe, Beneonitrile, 2,6-J> ibLalogen-4-oy8nphenylester of lower aliphatic acids and Ihiobensamide τοη group III, the e ^ r use in Cttk vrfinäung3g (male heft; i-Chlcr ^^ - MBCdi &thylamino'i-ij-triarins 2-Οήϊοι * -4 »6-1> 1β-

1C9821 / 2095

(ethylamino-8-triasin, 2 ~ chlorine «4 ~ ethylamino ~ 6" iEopropylainino-8-triasin, 2-chloro-4-ethylamino-6 ~ diethylaoiino ^ s-1; riasin _> 2-chloro-4-diethylamino ~ 6 --i8i> propylamino - 8-triazine, 2-methoxy-4,6-bie (ethylamino) -8-triaain, 2 "methoxy-4 _t 6" Mß (ißopropylaaino) «B-triazine, 2-chloro-4 »6 ~ bia (diisopropyleniino) -8-triasjin» 2-thio- ■ ethyl-4-öthylaDino-6 ~ ieopropylaraino-s - triaain, 2-4-bie (isopropylamino) -6 ™ methoxy-fi "triazine, 3-phenyl-1, i-diKethylharnetoff, 3- (p-chlorophenyl) -1,1-dimethylurea, 3- (3 * 4- "Bichlorpbenyl) -1,1-dimethylur8tuffp 3- (3 _f 4-dichlorophenyl) - 1-ri2etho3fy-1-oetbylurea ρ 1-n »Du1; yl-3- (5t4 ~ dichlorophenyl) -ne1: hylh3rn- Btof t, 1-phenyl-3- (2-ethylcyclohexyl) urea, p-chlorophenoxy- phenyl- N _{f N-dieethylharnetoff%} 1- (Tetrahydrodicyclopen1; adienyl) -3,3-dimethylharnetoff, 1,3-Bie (1-hydroxy-2,2,2 trichloroethyl ~) - 'urea, H ^ -CChlorphenoxyJ-phenyl-N 'H'-dimethylurea? 2,6-chlorobensonitrile, 3ί5-diiodo-4-hydroxybeneπl! OnitΓil _t diphenylaoetonitrile, 3,5-dibromo-4-hydroxybensone itril; 2,6-Diioö-4-cyanopheiiy lace fact, 2,6-dibromo ~ 4-cyBnophenylaceta t, 2.6 ~ 3) ii od-4-oyanophenylpropionat, 2,6-dibromo, "4" and Cyanophenylpropionat 2 _e 6 Chlorothiobenzamide.

Regarding the connections of group IV »dAe sturdy Yervrewdung in Combination with the compounds τοη group A cut formation

suitable
the means according to the invention include, for example; Methyl-S-ethyl-2,3e5 _? 6 "tetrachloromonothioterephthalate;methyl-S-ethyl-2; 3» 5 ₀ 6-tetx ^> achlormonothioterephthalat, methyl.-S - r-

1098 ^ 1/2095

ORlGiNAi * ί

propyl-2 _t 3f5p6-tetrachloromonothioterephthalate _f methyl-S-leopropyl-2 _t 3.5t6 "tetrachlorinonothioter9phthala1;, and methyl ~ S ~ nI} utyl2 ₉ 3 (5ff6-tetrachloraonothioterephthalate>

Exemplary fti? the compounds from group V ₉ which are suitable for use in combination with the compounds from group A to form the gowns according to the invention are: dimethyl-2,3,5-6 "-fcetrachlorotereph1;halai; _f methylethyl-2,3 , λ 5f6- tetrachlorterephthalat, Hethyl-n-propyl-2,3; 5 * tetrachlorterephthalat -6- 14ethylisopropyl and _2-t 3t5i6- "tetrachlorterephthalat.

According to one embodiment of the invention, the rate compound is from the group of compounds of the formula (A) ₉ in which A is chlorine or substituted lower alkyl groups, D is chlorine and £ is hydrogen and R% R and Z are defined above Alkali metals selected from those dietary compounds in which R 'Waseeretoff iet. In a further, preventive embodiment, the "wide connection" forms a connection of the poreel (I), in which Y COOL _P X ^ is hydrogen and X ₁ , X _2, X ^ and X ^ are chlorotones, bronzes, and thoxy groups independently of one another. n, Nitre ^? uppen »Aaiso groups or wise men- |

ι • toffatom "mean, ait der ÜsSgab";, d @ · Höcfestsns one of Beate X ₁ , X ₂ ^ X ^ and Xe Waseerstaff and their Salee, Aaido and Beter. The second variable βαβ of the Srupp

10 21/20 β

-u-

5t5t6-trieaXorbenso * acid, whose Beter, in which dl · rereeternde Group up to BU 10 contains carbon, the alkali of which grows <stt their Aainsalse, in which the Aainkoaponente up to su 10 Carbon atom · contains, and their amides, in which the Aainkoaponente contains up to BU 10 carbon stone, selected ·

For practical use as herbicides, the invention is used Combinations of active ingredients generally prepared as herbioid additives that are inert Carrier and an htrbioid toxic amount of the combination contain · Such herbioid additives or oils that suoh as rescue rescues can be received, enable one swetkaälige application of the Koablaatlon to the place of the Unkrauibeftlls in every desired «tight. This means kJtaaen solids, so «Example ftlubeaittel, Orunulste ocar beastsbsre Powder, or liquids, ia examples of Luauagea, aerosols or desulphurable contents.

leütpleltweitt kOnnea dust unit iuroh Teraahlen «ad Teraiaohen «Tr sctiren terbindongen old an essentially inert carrier, stta example Tslktai, clays, quarry earth, pyrophyllite mad of the » equally manufactured. Granular «preparations ktinaen duroh Iapregnierea green carrier, see example the Attepulgitea odtr dtß Vtraiouliten, usually old of a small size range

101121/2095

SAD ORiQINAL

of about O _# 3 Ms 1.5 mm, with the active compounds in the combination, usually as a solution in a suitable solvent or by coating an inert carrier with a preparation of the combination in the form of a wettable powder. Wettable powders, which can be öispergiert in water or oil to any desired to Konsentration of the combination can, parts by introducing Netaaitteln in Stäubeaittelkonzentrate or by Veraisehen the Erstand- ^ as in the case of the de Alkaliiaetallsalae: <r active ingredients are prepared.

In some cases the active compounds are in similar combinations In water or the usual organic solvents « sum for example kerosene or xylene, sufficiently soluble so that they can be used directly as solutions in these solvents. Often, solutions of herbicides under overpressure can be used as Aerosols are dispersed. Preferred liquid herbicidal agents are, however, emulsifiable concentrates that contain the invention · ι f Combination and as an inert carrier a solvent and in the case! an emulsifiable consume containing an emulsifying agent. j Such consensus rates can be applied as sprinkles to the Make the weed infestation with water and / or oil up to any desired Concentration of the combination can be stretched. The emollients most commonly used in these concentrates j and non-ionic cross-saxon agents or mixtures from non-ionic to anionic surface-active

109821/2085

■ - 16 -

Means, By using some Baulgieriaittelayateae can «ine inverted · emulsion (Vfasser / in oil) sub direct application on ron Weed infested areas are produced.

The compositions according to the invention can ala herbicides can be used in any known manner. Sin method of combating τοη weeds is that one of the The location of these weeds treated with a herbicidal agent, one inert carrier and, as an essential bed end part, a composition according to the invention in one for these weeds

contains herbicides toxic ifenge. The concentration of the new the

Means according to / invention In the preparation changes greatly with the type of preparation and for the purpose for which it is intended; in general, however, the herbicidal compositions contain from about 0.05 to about 95% by weight of the active combination according to the invention. In a preferred embodiment of the invention, the herbicidal agents contain about 5 to 75% by weight of the current combinations. The compositions könntn f "rn" r * "- sätällche materials, like other Pesticide, Insecticide gB, Bfe" o _^:> .- toclde, fungicides and the like, stabilizers, Spreit-, medium, Desaktiratoren, Adhesives ·, adhesives, Containing fertilizer activators, synergistic agents and the like

Weeds are undesirable plants in their location without economic scoops »which produce ron cultivated plants or the health of the cattle tanda impairiijeri. Number-

109821/7095

"'■■ 6AD ORIGINAL

rich species of weeds are known, including annuals, sun Beiapiel foxtail, white goosefoot, foxtail grass, wild mustard, field purseeds Engll6ch ~ ryegrass ₉ Knuterich? ndkraut ordinary S, wild oats "velvetleaf, Portuleäc, HUhnerhlree, knapweed, cocklebur" wild buckwheat, kochia ₉ alfalfa and Wa.eeerpfeffer, zweijähige, f.am as wild carrot, burdock, mullein, round-leaved shark _τβ ν common Natternkopf , common thistle, dog's tongue; Mrtten ~ woolly herb, matricaria and purple diet knapweed or perennial, sum Beiapiel dagger, dandelion? Bellflower, perennial raigraa, Ackerquec.ke, Sudan grass, Saudietel, bindweed, dog tooth grass, yarrow ₀ curled dock, cyprus grass, hordweed and barbara. Such weeds can also be classified as sessile or grassy weeds. For economic ör And s, it is desirable, "insudistnen the growth of such weeds," without Ifutspflansen or livestock suffer damage.

. ■■■ · ■■. ■ '■■■. ■ ■

The new agents according to this invention are for weed control special because they are used for many weeds and groups toxic, on the other hand for the urgent useful plants The contents are non-toxic «You have the exact amount of the agent. depends γόη of a number on factors, including for example the persistence of the individual weed species, the weather, tob The type of soil, the type of order and the type of sttn in the same area ·. So while the application of

bia zn only about 70 or 140 g of the · Korabination rön active

109821/2095

Compounds per hectare (1 or 2 ounces per acre) for good harvesting a slight infestation with weeds that grow under unfavorable conditions are sufficient, good control heavy infestation with resilient perennial weeds that grow under favorable conditions require the application of 11 kg of the combination of active compounds per hectare (10 lbs. per acre) or more.

The following examples illustrate some typical herbicides Means according to this invention. All quantities are given in Gewientstellen.

example 1 Manufacturing University; a wettable powder

The following ingredients are mixed thoroughly until one homogeneous «mixture is obtained. This powder is instant mixed with water to form an aqueous solution before application, which the desired concentration of the combination active * Contains compounds for use as an aerosol.

Potassium ae from MethQxy-4-chloro-2-methylphenoxyacetamine 80

Potassium ~ 2-methoxy- "3,6 ~ dichlorobeneoate 20

109821/2095

SAD ORIGINAL

Example 2 H first Settin g a J) enetgbaren powder ·

The following ingredients are mixed in a standard mixer Mix thoroughly and then grind to a powder having an average particle size of less than about 50 microns. The finished powder is in Viasaer with the desired Concentration of the combination of active compounds dispersed.

Sodium 2,3,6 "trichlorobenzoate 35 H-methoxy "2" methylphenoxyacetainide 40 Puller earth 22 _? 75 Sodium Lauryl Sulphate 2 Hethylocllulcse 0.25 Example 3 Manufacture of a wettable powder

The following beatand parts are mixed in a usual way direction intimately mixed and then ground to a desired particle size. Immediately before the order is placed the finished powder in the desired concentration of

109821/2095

- 20 combination of active compounds dispersed in water.

H-methoxy-2-methyl-4 ~

chlorophenoxyacetamide 50

Dimethylaminsala from

2- "fethoiy-3,6 ~ dichloro-

benzoic acid 20

Puller earth 25 Sodium lauryl sulfate, 3 Methyloelluloea 2 Example 4

1.

Production of a wettable pulver

The following ingredients are in a common mix device intimately mixed and then a powder with an average particle size of less than about 50 Klkron marry. The finished powder is placed in the water you want Consentration of the combination of active compounds dispersed.

Hethyl-S-ethyl-2,3 # 5 »6-1 · traohlor bonothioterephthalate 10

N-methoxy-N-ethyl-2 * methyl ~ 4-chlorophenoxyacetamide 15th

Attapulgite 70.5 Colloidal silicon dioxide 0.5 Oleic acid ester of sodium ethionate 2 Sulphonates of Pichtenhol «lignin 2

109821/2095

“AD ORIGINAL

Betapiel 5 Manufacture of a Cldleper ^ edible Powder

The following components are as in the previous example mixed and ground to a powder that can be diapered in oil to form a spray, which the desired concentration of the combination of active twists contains.

N-methoxy-H-methy1-4-chloro »

phenoxyacetaaid 40

3,4-dichloropropionic anilide 30

Cd deneation products from Diamly

phenol with xethylene oxide 4

Puller earth 26 Example 6

of a dusting agent8

The following ingredients are mixed thoroughly and then ground to a particle size of less than about 50 microns, resulting in a dusting agent suitable for application with conventional dusting equipment.

1ÖS821 / 2095

BATH

N-methoxy ~ 2 ~ methyl-4-chloro

phennxyacetaaid

2-methoxy-3, G-dichlorofcenzoic acid

Talc

Division of a granulate

The following are Beatandteile with enough water? .U a paste "mixed, which is then dried extrucJiert * urea milled, whereby grains are obtained which predominantly have a diameter about τοη O _r 79 to 6.35 na (1/32 1/4 ") to have. The grains are applied with fertilizer spreaders or other common equipment. «Pas dextrin in this preparation serves as a binding agent»

Dimethylamine salt γρη 2-methoxy 3,6 dichlorobenzoic acid

yyy

chlorophenoxyacctamide 5

Puller earth 66

Dextrin 20

Iiatrium lignin sulfonate 3

Kerosene i

109821/2095

BATH ORIGINAL

SI · Surprising herbicidal effectiveness of the invention Combinations became through unions to defeat detected by yogelknotweed. In these experiments, small pots made of plastic * those with dry earth were used filled were sown with bird knot terioh. 24 hours or less after sowing the pots were sprayed with water until the earth was damp and the test connections became in ports of aqueous emulsions of acetone solutions containing emulsifying agents "in the specified concentrations" applied to the surface of the floor. After spraying the pots were placed in the greenhouse, supplied with additional heat as required, and daily or watered more often. The plants were kept under these conditions for a period of 15 to 21 days. to At this point in time, the condition of the plants and the HqS of the damage to the plants on a scale from 0 to rated as follows:

0 * no damage

1.2 * slight damage ~

3.4 - moderate damage

5.6 * normal severe damage

7,8,9 * «no severe damage

10 ■ - * mortification

1Q9821 / 20S5

The unusual effectiveness of these combinations IbComparison on the individual components is based on the

the following results of these experiments:

Teetve oil bonds dosage, evaluation of the

actual cons., damage to former verb.

DMA 0.23 (1/5)

Connection A 0.28 (1/4) 8

DMA * 0.23 (1/5) '2

Connection A 0.28 (1/4) 3.5

/ ■

DltA-dimethylamine salt of 2-methoxy-3,6-dlchlorobenzoic acid.

Compound A «H-methoxy-2-methyl-4-chlorophenoxyacetamide.

The combinations according to the invention are also unusually effective as herbicides in comparison with other combinations of known herbicides. Example catfish were carried out in an experiment field tests to control bluebells. With these solid the combinations listed below were sprayed in the form of aqueous emulsions of emulsifying agent-containing aoeton solutions in the specified dosage amounts on several places where the lawn weeds were. 43 days after application, the treated areas were examined and the weed control compared to untreated areas was determined. In the following bind some results of these experiments are given:

109821/2095

BATH ORIGINAL

Test-
come mnat ions dosage
kg / ha (Ib./aere) DHA
Connection A 0.56 p / 2)
1.13 (1) DMA
Connection Λ 1.13 (1)
1.13 (1) BHA
2,4-D 0.56 (1/2)
1.13 (1) 2.4 - D
2 ₉ 4.5-T 1.13 MJ
1.13 (1)

100

100 0

2 »4-D 2.26 (2) 50

DÄAaDimethylaminealz of 2-methoxy-3,6-dichlorobenzoic acid Compound A-N-Methoxy-2-methyl-4-chlorophenoxyacetamide.

The above-described teet was repeated in places where there was yarrow. "The combinations of compounds listed below, which were prepared as aqueous emulsions of acetone solutions containing detergents, were sprayed onto the places at the concentrations indicated" for 32 days after application, the sites were unterauoht, and the fight against .Schafgarbe t was evaluated according to the following scale:

excellent control, - ..:

little control or no «control.

109821/7095

In the table below are some of the results of this Attempts listed:

Test-
coabinations dosage
keAa ( ib./acre) control DMA
Connection A Pf ⁴ J excellent DMA
Connection A H DNA "
2 _# 4-D Ιϊ ^{/ 2} 1 no no 2.4 ^ D (2) small amount

DIlA * Diaethylamine as ron 2-methoxy- * 3 »6 ~ dichlorobens; oe-

acid.

Compound A * 3J-Methoxy-2-methyl-4-chlorophenoxyacetamide.

The compounds of group A old of the poreel (A) can by setting the corresponding acyl halides according to the Methods can be made which are detailed in US Pat 5 027 407, 3 166 589, 3 166 591 and 3,168,561.

109821/2095

8AD ORIGINAL

The alkali metal salts of those compounds τοπ group A, in which fi · in formula (A) denotes Voseeretoff, all of which have been referred to above particularly partially, can be obtained from the corresponding, suitably white II-alkoxy-ring substituted phenoxyalkylaaides by treatment with an equivalent amount jilkalimetallhydroxyd urSd ErwÜraaen - if necessary - are produced. The reaction can be carried out by heating - if necessary - in a solvent, for example an alcohol or an alcohol-ketone mixture, for example an ethanol-dioxane mixture. Get noticed desired 3al "can consist of Reaktionsaischung by evaporating the solvent ·· * mittete, if one was used by extraction ^': and the like are obtained.

109821/2095 _BAD

Claims (8)

■ - 28 - P a t, S1 η. t ^ a η S1P rite h s 1. Herbicidal agents containing a first compound of the formula OR H Π 'if where A, hydrogen, chlorine, unsubstituted lower alkyl groups or unsubstituted lower alkenyl groups, D is hydrogen, Hslögenatome, unsubstituted alkyl groups or unsubstituted lower alkenyl groups and £ hydrogen or chlorine, with the proviso that at most one of the radicals A and D is hydrogen, A only for chlorine, if D is chlorine and £ only chlorine, wc in both of a and D is chloro, R 'is a Wasseret "ff atom or an alkyl group R' is an alkyl group and _f ^ Z is an unsubstituted alkylene group ■ it 1 to 4 carbon atoms, or the alkali metal salts of those compounds in which Ji * denotes hydrogen and at least one other compound is selected from the following group of compounds, see: 109821/2095 BAD ORtGiNAU (i) Connections of the poreel ⁵ ffi ⁱ where X ₁ , Xg ₁ , Χ, _β Xj and X- independently of one another halogen atoms, lower alkyl groups, lower alkoxy groups, nitro groups, amino groups, pheaylsets or hydrogen atoms, provided that at most two of the radicals X ₁ , and Xc is hydrogen atom aind, and Y is -OH ₉ or -COOH, in which 21 is an integer from 1 to 3 and its SalsQß, amides and esters; ; X3 * (II) herbicidally active carbamates and shiocarfcamats; (III) herbicidally active a-Triasifi®, ureas, bensonitriles, 2,6-dihalo-4-cyanophenyleate, lower aliphatic acids and thioben-amides; _t (2Y) compounds of the formula Gl Cl where R "means a lower alkylreet? (V) compounds of the formula C-O-R " Gl Cl
wherein R "represents a lower alkyl radical; (VI) 3i> 4-I) iohlorpropionanilid and (VII) 4 ~ Afäino-3,5,6-triohlorpicolinic acid. 2 «means according to claim 1, characterized in that A Chlorine or an unsubstituted lower / alkyl group, D means chlorine and E means waaeeretoff. 3. Composition according to claim 1 or 2, characterized in that the second compound is a he ^ biciö active compound of the formula of group I «wherein Y -GOOHp X, H and X ₁ - X ^, X ^ and Χ- independently of each other Chiorstom ·, Bromate n ie 109821/2095 ÖAD ORIGINAL - 51 - HetUoxygruppen, nitro groups, amino groups or Wasserstoffa "tame mean, with the proviso ,, AEAI most one of the residues X ^, X * _r Xg and Xk is hydrogen, or a string, amide or ester thereof. 4. Composition according to claim 1 _f, characterized ₉ that it is the second compound 2 "methoxy-3« 6 ~ dichlorobenzoic acid, 2-methoxy-3f5 »6-triohlorbenzo @ acid _s their esters, in which the esterifying group Ms to 10 Contains carbon atoms whose alkali metal sols, their amine salts, in suitable the amine component contain up to 10 carbon atoms, or their amides, in which oils contain amine components, contain 10 carbon atoms. 5. Means according to claim 1, characterized in that; The first compound was an alkali metal salt of Hethoxy-2-methyl-4-chlorophenoxyacetamide and the second was an alkali metal salt bond an alkali metal salt τοη 2 - ^ 'lethoxy ~ 3,6-diochlorobenzoic acid contains. 6. Composition according to claim 1, characterized in that it is the first compound N-methoxy-2-methyl-4 ^ chlorophenoxyacetamide and the second compound is Me thy IS-me thy 1-2,3, Sea-tetruehlormonothioterephthalat, Kaliua ~ 2 -me'choxy-3t6-dichlorobenzoate _: Egg that contains dimetarylamine and 2 -ethoxy-3-6-dichlorobenzoic acid. 109821/2095 BATH 7. Herbicidal compositions containing an inert Carrier and a herbicidally toxic amount of an agent according to any one of claims 1 to 6. ■ 8. A method for killing unwanted plants, characterized in that the plants are nit one herbicidal agent still one of the claims. «1 to 7 In brings into contact with a quantity which is harmful to the plants. 109821/2095 BAD ORJGfNAL