DE3110523C2 - 2'-Trifluoro-methyl-2-chloroacetanilide and herbicides containing them - Google Patents

Abstract

The invention relates to a group of N-hydrocarbyloxymethyl-2-haloacetanilide compounds, herbicide preparations which have these compounds as active ingredients, and methods for using these herbicides in various crops of useful plants, in particular maize and soybeans, but also other crops such as cotton, peanuts, rape, French beans, wheat and sorghum. The herbicides according to the invention are particularly effective against perennial weeds that are difficult to kill, such as couch grass and cyper aceae, but they are also effective against annual weeds.

Description

The invention relates to new 2'-trifluoro-methyl-2-chloroacetanilides of the general ones given below

Formulas which have herbicidal properties and herbicides containing them as active ingredients.

2-chloroacetanilides, which are substituted on the nitrogen atom by alkoxy or alkyl radicals and have various ring substituents, are from BE-PS 8 10 763, US-PS 39 66 811 and 41 52 137, DE-OS 24 02 983, GBPS 20 13 188 and ZA-PS 74/0 767 known. However, none of these known 2-chloroacetanilides is _{substituted in O-slope by CF 1} or the alkylene portion of the alkoxyalkyl group contains at least 2 carbon atoms. Detail-

Lated information on the herbicidal effectiveness of the known 2-chloroacelanilide can be found in the above Patents not, it is only stated therein that some of the known compounds

are effective on a large number of weeds without further details regarding their herbicidal active

to be found in it.

An extremely useful and desirable property of herbicidally active compounds is their ability to

Keeping weeds under control for a longer period of time, the longer their effect is, the better it persists during the growing season. With many of the known herbicides one will be sufficient Weed control only reaches two to three weeks before the compound reaches its phytotoxic effectiveness loses. Accordingly, a disadvantage of most of the known herbicides is their relatively short lifespan in the soil. Another disadvantage is that their effectiveness is impaired by heavy rains, which many

inactivate the known herbicides. Also, the known herbicides are only available on certain types of soil applicable. While some known herbicides are only effective in soils with a low organic matter content others are only effective in soils with a high proportion of organic matter. A disadvantage of the vieter known herbicides also consists in the fact that they can only be applied in a very special way, for example by applying it to the surface before emergence or by working it into the ground,

w) by application before or after planting. Furthermore, some of the known herbicides are extremely toxic, so that special precautions must be taken in handling them.

Aulgahe tier invention was therefore to add new compounds with a pronounced herbicidal effective wedge linden that can be used on all types of soil and incorporated into the soil using any method or can be applied to the surface of the soil and the surface of the / u controlling plants,

(.5 without endangering the environment, and their effectiveness over periods of up to Lasts 12 weeks without being adversely affected by heavy rains that have fallen in the meantime.

It has now been found that this object can be achieved according to the invention by means of special 2'-trifluoromethyl-2-chloroacetanilides the general formula

where mean:

either R _{1 is} hydrogen and R is isopropyl

or R, methyl and R Ci-5-alkyl, alkoxyalkyl, alkenyl or alkynyl with up to 5 carbon atoms

or R | Ethyl and R ethyl, n-propyl or isopropyl.

The compounds according to the invention have a pronounced herbicidal activity, up to Lasts 12 weeks and is not affected by heavy rains that have fallen in the meantime. she have only a low toxicity, so that no special precautionary measures whatsoever are required for their handling must be taken and they can be handled safely. They are effective against those that are difficult to kill perennial and annual weeds, especially couch grass, yellow or purple sedge (Cyperaceae) and against a wide range of annual weeds, including those that are so difficult to kill annual weeds such as Sorghum halepense seedlings, Sorghum bicolor, Brachiaria plantaginea, Panicum species (texanum and miliaceum), Oryza sativa and Rottboellia exaltata. Besides, they are also suitable to control other harmful perennial and annual weeds, such as. B. Herbstpanicum, Polygonum sp., Chenopodium album, Amaranthus, foxtails (e.g. Setaria faberi and lutescens), Digitaria sanguinalis, Echinochloa crus-galli, Ipomoea sp., Abutilon theophrasti, Xanthium pensylvanicum, Portulac, Sesbania exaltata and Sida spinosa.

Preferred compounds of the general formula given above are those in which R | Means methyl or ethyl and R represents a C ₂ j-alkyl radical. Individual particularly preferred compounds of the invention are as follows:

N-ethoxymethyO ^ '- trifluoromethyl-o'-methyl ^ -chloroacetanilide; N-yn-propoxyrnethyO ^ '- trifluoromethyl-o'-methyl ^ -chloroacetanilide; N-isopropoxymethyl ^ '- trifluoromethyl-o'-methyl ^ -chloroacetanilide;

N-Osobutoxymethyö ^ '- trifluoromethyl-o'-methyl ^ -chloroacetanilide;

N-ethoxymethyO ^ '- trifluoromethyl-o'-ethyl ^ -chloroacetanilide; N-yn-propoxymethyl ^ '- trifluoromethyl-o'-ethyl ^ -chloroacetanilide; N-UsopropoxymethyD ^ '- trifluoromethyl-o'-ethyl ^ -chloroacetanilide; N-OsopropoxymethyO ^ '- trifluoromethyl ^ -chloroacetanilide;

NHAllyloxymethyl ^ '- trifluoromethyl-o'-methyl ^ -chloroacetanilide;

N- (propargyloxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide; N- (2-methoxyethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroac.; Tanilide;

The invention also relates to herbicides which are suitable for controlling undesirable plants in Crops of useful plants, especially in maize crops, soybean crops, cotton crops, rapeseed crops and French bean cultures containing at least one 2'-trifluoromethyl-2-chloroacetanilide of the above Type contained in a herbicidally effective amount and at least one conventional additive.

The herbicides of the invention are useful on all types of soil, from light organic soils to heavy clays and peat soils. They can be applied in any way, for example by applying on the surface of the soil or by working it into the soil. With their help it can be difficult to kill control and / or push back perennial and annual weeds of the abovementioned species, while they are harmless to a wide variety of crops, particularly corn and soybeans, however also for others, including cotton, peanuts, canola, French beans, wheat and / or sorghum. Your herbicidal Effectiveness in the soil lasts for periods of up to 12 weeks and they are against leaching or dilution resistant to high humidity, for example heavy rainfall. You are flexible in yours Application, d. that is, they can be applied, for example, to the surface of the soil prior to emergence or worked into the ground.

An essential property of the herbicide preparations according to the invention is their ability to produce a broad Keeping spectrum of weeds under control. This includes weeds caused by common herbicides can be controlled, as well as a variety of weeds that individually or collectively so far Missed control by a single class of known herbicides. At the same time they are harmless to cultures one or more crops, including in particular corn and soybeans, but also others such as Cotton, peanuts, canola, sorghum, wheat, and French beans include. While the well-known herbicides useful for controlling a range of weeds and occasionally certain resistant weeds are, the unique herbicides of the invention have been shown to be capable of a variety of resistant To control perennial and annual weeds or to push them back to a large extent, according to the perennial Weeds couch grass, yellow and purple sedge (Cyperaceae), annual broad-leaved weeds such as Sida spinosa, Sesbania exaltata, Polygonum sp., Chenopodium album, Amaranthus, and annual grasses such as

Sorghum halepense seedlings, Sorghum bicolor, Brachiaria plantaginea, Panicum texanura, Panicum miliaceum, Oryza sativa, Rottboellia exaltata, as well as other harmful weeds such as autumn panicum, foxtails, Echinochloa crus-galli and Digitaria sanguinalis. An improved weed reduction also became resistant to weeds like Ambrosiaceae, Abutilon theophrasti, Ipomoea sp., Xanthium pensylvanicum and Portulac.

The compounds according to the invention can be prepared as described in Example 1 below are by N-alkylation of the anion of a suitable secondary 2-haloacetanilide with a Alkylating agent under basic conditions. A modification of the N-alkylation procedure is that in situ production of halomethyl alkyl ethers, which are used as starting materials in the aforementioned N-alkylation process can be used. This modification is described in more detail in Example 2 below.

example 1

In this example the preparation of N - (EthoxymethyD ^ '- trifluoromethyl-o'-methyl ^ -chloroacetanilide described.

4.02 g (0.016 mol) 2'-trifluoromethyl-6'-methyl-2-chloroacetanilide, 3.02 g (0.032 mol) chloromethyl ethyl ether and 2.0 g of benzyltriethylammonium bromide (phase transfer catalyst) were dissolved in 75 ml of methylene chloride in a 500 ml flask with a round bottom, equipped with a mechanical stirrer and thermometer was. 15 ml of 50% sodium hydroxide was added all at once with vigorous stirring, resulting in led to an exothermic heat build-up of up to 26 ° C. After about 5 minutes, gas chromatography indicated that the Response was complete. After 15 min, ice and water were added, the layers separated, and the organic Layer washed out with 2.5% sodium chloride, dried, filtered off and stripped. The dark one The residue was Kugelrohr distilled, and 3.4 g of a yellow oil fraction, boiling point 110-115 ° C. at 13.3 Pa, were obtained collected. This fraction was taken up in cyclohexane and purified by HPL chromatography, using 20% ethyl acetate in cyclohexane. Further Kugelrohr distillation of the peak fraction gave 3.2 g (65% yield) colorless oil, boiling point 100-110 ° C / 13.3 Pa, a white dye crystallized on standing, Mp. 41-43 ° C, from.

30 Elemental analysis door C |, H, X1F, NCM%): Calculated: C, 50.41; H 4.88; N 4.52; Found: C, 50.02; H 4.81; N 4.38.

Example 2

This example describes the use of an improved alternative method according to which the compounds according to the invention can be prepared. A peculiarity of this process is that in situ Preparation of the alkylating agent, which makes the process more effective, more economical and simpler.

A slurry of 7.3 g (0.096 mol) ethylene glycol monomethyl ether and 1.44 g (0.048 mol) para

formaldehyde in 100 ml of methylene chloride solvent was cooled in an ice water bath and 5.9 g (0.048 mol) of acetyl bromide was added. After stirring for 45 minutes, 4.0 g (0.016 mol) of 2'-trifluoromethyl-6'-methyl-2-chloroacetanilide and 2.0 g of benzyltriethylammonium chloride were added. Then 50 ml of 50% NaOH were added all at once. Gas chromatography indicated that the reaction was complete in about 5 minutes. Ice and water were added to the mixture to cause phase separation, the organic phase was then separated, dried, filtered off and stripped. The residue was distilled in vacuo to give 4.2 g (77% yield) of a clear colorless oil, bp. 150-160 ⁰ C / 13.3 Pa.

50 Elemental _{Analysis Door C M} H, ₇ C1F, NO.! (%): Calculated: C 49.49; H 5.04; N 4.12; Found: C, 49.33; H 5.04; N 4.08.

The product was identified as N- (2-methoxyethoxymethyl) -2'-trifl'jormethyl-6'-methyl-2-chloroacetanilide.

If the N-alkylation process allows temperatures to develop that are too high or too low, then different Impurities arise, e.g. B. sec.-anilide, the corresponding imidate, a-alkoxyamide or Diketopiperazine. Such impurities can be removed by washing out the organic layer with a Remove dilute aqueous hydrochloric acid solution, e.g. B. 2-3% NaCl or 5% HCl.

Examples 3 to 13

Virtually the same procedures, reactant amounts and amounts described in Example 1 or 2 were used general conditions were used, but the appropriate secondary starting anilides and were used in each case Alkylating agents used to make the final product, namely further compounds of the invention of the above Make formula; these compounds are listed in Table 1.

Table I.

At connection

Empirical
formula

Bp. ⁰ C
(Pa)

LIemenl

Elemental analysis

calculated the

3 N- (isopropoxymethyl) -2'-trifluoromethyl-2-chloroacetanilide

4 N- (n-Propoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide

5 N- (isopropoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide

6 N- (isobutoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide

7 N- (methoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide

8 N- (n-Butoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide

9 N- (sec-Butoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide

10 N- (allyloxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide

11 N- (Propargyloxymethy0-2'-trifluoromethyl-6'-methyl-2-chloroacetanilide

12 N- (isoamyloxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide

13 N- (ethoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide

14 N- (n-Propoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide

15 N- (isopropoxy methyl) -2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide

The secondary used as starting material for the preparation of the compounds according to the invention Anilides are best made with conventional chlorination of the appropriate primary amine, as described in Example 16.

C ₁₁ H ₁₅ F ₁ CINO, 100-101 C. 50.41 50.52 (6.7) H 4.88 4.89 N 4.52 4.46 C ₁₄ H ₁₇ ClF ₁ NO ₂ 110-120 C. 51.94 51.80 (13.3) H 5.29 5.17 N 4.33 4.28 C ₁₄ H ₁₇ CIF ₃ NO ₂ 110-120 C. 51.94 51.69 (13.3) H 5.29 5.23 N 4.33 4.22 C ₁₅ H ₁₁₁ ClF ₃ NO ₂ 130-140 C. 53.34 53.07 (13.3) H 5.67 5.61 N 4.15 4.01 C ₁₂ Hi ₃ ClF ₃ NO ₂ oil C. 48.47 49.94 H 4.43 4.44 N 4.74 4.70 C ₁₅ H ₁₁₁ CIF ₃ NO ₂ 135-138 C. 53.34 53.32 (6.7) H 5.67 5.68 N 4.15 4.14 C ₁₅ H ₁₁₁ CIF ₃ NO ₂ 135-142 C. 53.34 53.23 (6.7) H 5.67 5.67 N 4.15 4.13 C ₁₄ H ₁₅ ClF ₃ NO ₂ 123-125 C. 52.27 52.11 (13.3) H 4.70 4.74 N 4.35 4.34 C ₁₄ H ₁₃ ClF ₃ NO ₂ oil C. 52.59 52.44 H 4.10 4.14 N 4.38 4.34 C ₁₆ H ₂ , C1F ₃ NO ₂ 150 C. 54.63 54.66 (6.7) H 6.02 6.03 N 3.98 4.00 C ₁₄ H ₁₇ ClF ₃ NO ₂ 133-135 C. 51.94 51.32 (2.67) H 5.29 5.26 N 4.33 4.39 C ₁₅ H _n CiF ₃ NO ₂ Colorless C. 53.34 53.74 oil H 5.67 5.77 N 4.15 4.16 C ₁₅ H _n CIF ₃ NO 100-105 C. 53.34 53.43 (1.33) H 5.67 5.74 N 4.15 4.18

Example 16

The production of the secondary anilide is described here, which is used as the starting material for the production a compound of the invention, d. H. the compound of Example 13 is used.

6.0 g (0.03174 mol) of 2-trifluoromethyl-6-ethylaniline were dissolved in 75 ml of toluene and 3.77 g (0.033 mol) of chloroacetyl chloride were carefully added. The resulting slurry was heated to reflux temperature and held there for 4 hours. Then the mixture was diluted with an equal amount of hexane, then the mixture was allowed to stand. The product crystallized out and the solid obtained was filtered off and air dried; it yielded 5.8 g (69% yield); the filtrate was stripped to give an additional 2.7 g of white solid, mp. 121-124 ⁰ C (sealed tube).

Elemental Analysis for C ,, H,, CIF ₃ NO (%): Calculated: C, 49.73; H 4.17; N 5.27; Found: C 49.36: H 4.09: N 5.38.

The product was identified as 2'-trifluoromethyl-6'-ethy! -2-chloroacetanilide.

Primary amines of the type used to make secondary anilides by haloacetylation as described above are known in the literature; compare z. See the aforementioned U.S. Patent 39 66 811 and GB-PS 20 13 188.

The herbicidal preparations according to the invention, including the concentrates, before use Must be diluted, contain at least one active ingredient and a customary additive in liquid or solid form. The preparations are made by mixing the active ingredient with a customary additive, for which purpose

Diluents, extenders, carriers and conditioning agents are manufactured so that accessories i

preparations in the form of finely divided solid particles, granules, pellets, solutions, dispersions or emulsions

sions arise. The active ingredient can thus with a customary additive such as a finely divided solid, a |

Liquid of organic origin, water, a wetting agent, a dispersing agent, a j |

Emulsifying agents or a suitable combination thereof can be used. Ü

The herbicide preparations according to the invention, in particular liquids and wettable powders, contain

th preferably one or more surface-active agents (surfactants) in sufficient form as conditioning agents

appropriate amounts to make a particular preparation easily dispersible in water or oil. The on- ii

adding a surface active agent to the preparations significantly enhances their effectiveness. Under; | j

the term "surfactant" includes wetting agents, dispersants, suspending agents

and emulsifying agents. Anionic, cationic and nonionic agents can be used equally ||

will. S |

Preferred wetting agents are alkylbenzene and alkylnaphthalene sulfonates, sulfated fatty acid alcohols, ΐΙ

Amines or acid amides, long-chain acid esters of sodium isothionate, sodium sulfosuccinate esters, sulfated wj

or sulfonated fatty acid esters, petroleum sulfonates, sulfonated vegetable oils, ditertiary acetylenic glycols, $

Polyoxyethylene derivatives of the alkylphenols (in particular isooctylphenol and nonylphenol) and polyoxyfe

ethylene derivatives of the higher fatty acid monoesters of hexitol anhydrides (e.g. sorbitan). Preferred dispersion ξ

agents are methyl cellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkyl naphthalene sulfop ,

nate, sodium naphthalene sulfonate and polymethylene bisnaphthalene sulfonate. : ^; j

Wettable powders are preparations that are dispersible in water and contain one or more active ingredients, a; Vi

contain inert extender and one or more wetting and dispersing agents. The inert ||

Extensive solids are usually of mineral origin, e.g. B. natural clays, diatomaceous earth and synthetic | 'ΐ

Table minerals made from silica gel and the like. Such extenders include kaolinite, attapulgite clay and syntheti- i-jj

magnesium silicate. The wettable powders of the present invention usually contain about 0.5 to; |

60 parts (preferably 5 to 20 parts) active ingredient, about 0.25 to 25 parts (preferably 1 to 15 parts) ^

Wetting agent, about 0.25 to 25 parts (preferably 1.0 to 15 parts) dispersant, and 5 to | j

about 95 parts (preferably 5 to 50 parts) of inert stretch solids, all parts based on the weight of the 3rd

related to the entire preparation. If necessary, about 0.1 to 2 parts of the inert stretch solid K

be replaced by a corrosion inhibitor or foam inhibitor, or both. |

Other formulations contain dust concentrates that contain 0.1 to 60% by weight of active ingredient on a suitable stretch

agent included; these dusts can be used in concentrations of about 0.1 to 10% by weight; 1

be thinned. S.

Aqueous suspensions or emulsions can be prepared by adding an aqueous mixture of

a water insoluble active ingredient and an emulsifying agent until uniform and then i

homogenized so that a stable emulsion of very finely divided particles is obtained. The case entste- y rising concentrated aqueous suspension is characterized by its extremely small particle size, so that;.

after thinning and spraying the coating is very uniform. Appropriate concentrations of these Ϊ;

Preparations contain about 0.1 to 60% by weight, preferably 5 to 50% by weight, of active ingredient, the upper limit being £

is determined by the solubility limit of the active ingredient in the solvent. '. *

Another type of aqueous suspension encapsulates a water-immiscible herbicide, see above;

that a microcapsule phase dispersed in an aqueous phase is formed. In one embodiment, ä

very small capsules formed by adding an aqueous phase containing a lignosulfonate emulsifier, g

brings together a water immiscible chemical and polymethylene polyphenyl isocyanate that are not g

water-miscible phase dispersed in the aqueous phase and then a polyfunctional amine |

admits. The isocyanate and amine compounds react and form a solid urea shell around particles of the y < Chemical immiscible with water, so that microcapsules of the same are formed. In general, the ff

Concentration of the encapsulated material at about 480 to 700 g / liter, preferably 480 to 600 g / liter of the U

entire preparation. ij

Concentrates are usually solutions of the active ingredient in water that is immiscible or only partially miscible with water

Solvents, along with a surfactant. Suitable solvents for the active ingredient according to the invention i |

are i.a. Dimethylformide, dimethyl sulfoxide, N-methylpyrrolidone, hydrocarbons and not with water ijj

miscible ethers, esters or ketones. However, other strong liquid concentrates can also be dissolved by dissolving ^

the active ingredient in a solvent and subsequent dilution, e.g. B. with kerosene, for spray concentrate; j ?,

tration can be prepared. §

The concentrate preparations generally contain about 0.1 to 95 parts (preferably 5 to 60 parts) of | i

Active ingredient, about 0.25 to 50 parts (preferably 1 to 25 parts) surfactant and, if necessary, about 4 to 94 parts fi

Solvent; all parts are parts by weight and based on the total weight of the emulsifiable oil. G;

Granules are physically stable, particulate preparations that contain an active ingredient that acts on a W

Matrix of inert, finely divided, particulate extender adheres or is distributed in the same. Around 5;

To support leaching of the active ingredient from the particles, a surface-active Ά can be used in the preparation.

Means as listed above must be available. Natural clays, pyrophyllites, hats, and vermiculites are; j _:

Examples of useful types of particulate mineral extenders. Preferred extenders are porous, absorptive, preformed particles, such as preformed and sieved particulate attapulgite or Particulate vermiculite expanded by heat, as well as finely divided clays such as kaolin clays, hydrogenated attapulgite or bentonite clays. These extenders are used to produce the herbicidal granules the active ingredient sprayed or mixed. 5

The granule preparations according to the invention can contain about 0.1 to 30 parts by weight, preferably about 3 up to 20 parts by weight of active ingredient per 100 parts by weight of clay and 0 to about 5 parts by weight of surfactant per Contains 100 parts by weight of clay particles.

The preparations according to the invention can also contain other additives, e.g. B. fertilizers, other herbicides or pesticides or protective substances which are used as additives alone or in combination with one of the above io listed additives are used. Chemicals suitable for combination with active ingredients according to the invention are useful include Triazines, ureas, carbamates, acetamides, acetanilides, uracils, acetic acid or Phenol derivatives, thiol carbamates, triazoles, benzoic acids, nitriles and biphenyl ethers, such as. B.

Heterocyclic nitrogen / sulfur derivatives 15

2-chloro-4-ethylamino-6-isopropylamino-s-triazine 2-chloro-4,6-bis- (isopropylamino) -s-triazine 2-chloro-4,6-bis (ethylamino) -s-triazine

3-Isopropyl-1H-2, 1,3-benzothiadiazin-4- (3H) -one-2,2-dioxide 20

3-Amino-1,2,4-triazole 6,7-dihydrodipyrido (1,2-a: 2 '-, 1'-c) pyrazidiinium salt 5-Bromo-3-isopropyl-6-methyluracil l, r-Dimethyl-4,4'-bipyridinium

Ureas

N '- (4-chlorophenoxy) -phenyl-N, N-dimethylurea N, N-dimethyl-N' - (3-chloro-4-methylphenyl) -hamea

3- (3,4-dichlorophenyi) -1, l-dimethylurea. 30th

1,3-Dimethyl-3- (2-benzothiazo! y!) -urea 3- (p-chlorophenyI) -1, l-dimethylurea i-Butyl-3- (3,4-dichlorophenyl) -l-methylurea

Carbamates / thiol carbamates 35

2-chloroallyl diethyldithiocarbamate S- (4-chlorobenzyl) -N, N-diethylthiol carbamate isopropyl N - ^ - chlorophenyO-carbamate

S ^ .S-Dichloroallyl-r ^ N-diisopropylthiol carbamate 40

Ethyl N ^ -dipropylthiol carbamate S-propyl dipropyl thiol carbamate

Acetamide / Acetanilide / Aniline / Amide

2-chloro-N, N-diallylacetamide N, N-dimethyl-2,2-diphenylacetamide

N ^^ - Dimethyl-S-KitrifluormethyO-sulfonyl-aminol-phenylJ-acetamid

N-isopropyl ^ -chloroacetanilide

2'-6'-Diethyl-N-methoxymethyl-2-chloroacetanilide 50

2'-methyl-6'-ethyl-N- (2-methoxyprop-2-yl) -2-chloroacetanilide ff, ör, ir-trifluoro-2,6-dinitro-N, N-dipropyI-p-toluid! N N- (1,1-Dimethylpropynyl) -3,5-dichlorobenzamide

Acids / Esters / Alcohols 55

2,2-dichloropropionic acid, 2-methyl-4-chlorophenoxyacetic acid 2,4-dichlorophenoxyacetic acid

Methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propionate 60

3-Amino-2,5-dichlorobenzoic acid, 2-methoxy-3,6-dichlorobenzoic acid, 2,3,6-trichlorophenylacetic acid N-1-naphthylphthalamic acid

Sodium 5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate 65

4,6-dinitro-o-sec-butylphenol

N- (phosphonomethyl) -glycine and its C 1-6 monoalkylamine and alkali metal salts and combinations the same.

2,4-dichlorophenyl ~ 4-nitrophenyl ether
2-chloro-ii, u ', fl ^r -trifluor-p-tolyl-3-ethoxy-4-nitrodiphenyl ether

various

2,6-dichlorobenzonitrile!
Monosodium acid methanar sonate
Disodium methanar sonate

Fertilizers that can be used in combination with the active ingredients are ζ. Β. Ammonium nitrate, urea, potash and superphosphate. Other useful additives include Substances in which plant organisms take their roots and grow, e.g. B. compost, manure, humus and sand.

For herbicidal preparations of the type described above, various examples are given below Embodiments indicated.

I. Emulsifiable concentrates% by weight

A. Compound of Example No. 1 50.00

Calcium dodecylbenzenesulfonate / polyoxyethylene ether mixture 4.85

Calcium dodecylbenzenesulfonate 0.15

C ₉ aromatic solvent 45.00

100.00

B. Compound of Example No. 4 85.0

Calcium dodecyl sulfonate / alkylaryl polyether alcohol mixture 4.0

C ₉ aromatic hydrocarbon solvent 11.0

II. Liquid concentrates

100.0

30th

C. Compound of Example No. 6 5.0

Calcium dodecylbenzenesulfonate / polyoxyethylene ether mixture 1.0

Xylene 94.0

100.0

A. Compound of Example No. 4 10.0

Xylene 90.0

100.0

B. Compound of Example No. 5 85.0 dimethyl sulfoxide 15.0

100.0

C. Compound of Example No. 6 50.0 N-methylpyrrolidone 50.0

100.0

50

D. Compound of Example No. 7 5.0 Ethoxylated Castor Oil 20.0 Rhodamine B 0.5, dimethylformamide 74.5

100.0

III. Emulsions

A. Compound of Example No. 12 40.0

Polyoxyethylene / polyoxypropylene block copolymer with butanol 4.0

Water "'56.0

100.0

B. Compound of Example No. 13 5.0

Polyoxyethylene / polyoxypropylene block copolymer with butanol 3.5

Water "'91.5

100.0

IV. Wettable powders

A. Compound of Example No. 1 Sodium Ligna.-Jlfonate Sodium N-methyl-N-oleyl taurate Amorphous silica (synthetic)

Compound of example no.12

Sodium dioctyl sulfosuccinate

Calcium lignosulfonate

Amorphous silica (synthetic)

C. Compound of Example No. 13 Sodium Lignosulfonate Sodium N-methyl-N-oleyl taurate Kaolinite gate.

Wt%

25.0

3.0

1.0 71.0

100.0

80.00 1.25 2.75

16.00 100.00

10.0

3.0

1.0 86.0

100.0

V. Dusts

A. Compound of Example No. 7 Attapulgite

B. Compound of Example No. 8 Montmorillonite

Compound of Example No. 9 Bentonite

D. Compound of Example 10 Diatomaceous Earth

VI. Granules

A. Compound of Example No. 1

Granulated attapulgite (20/40 sieve)

Compound of Example No. 6 Diatomaceous Earth (20/40)

Compound of Example No. Bentonite (20/40)

D. Compound of Example No. Pyrophyllite (20/40)

2.0 98.0

100.0

60.0 40.0

100.0

30.0 70.0

100.0

1.0 99.0

100.0

15.0 85.0

100.0

30.0 70.0

100.0

0.5 99.5

100.0

5.0 95.0

100.0

VI. Microcapsules

A. Compound of Example No. 1 encapsulated in a polyuret shell Sodium lignosulfonate water

49.2

0.9

49.9 100.0

Wt%

B. Compound of Example No. 12 encapsulated in polyurea cup 10.0

Potassium Lignosulfonate 0.5

Water 89.5

100.0

C. Compound of Example No. 13 encapsulated in polyurea shell 80.0

Magnesium salt of lignosulfate 2.0

Water 18.0

100.0

Effective amounts of the acetanilides of the invention are applied to the soil containing the plants or taken up in an appropriate manner in aqueous media. The application of the preparations as Liquids and solid particles on the earth can be done using conventional methods, e.g. with motorized atomizers, Tank and hand sprayers or spray atomizers. The preparations can because of their effectiveness can also be distributed in small doses by airplanes as dust or spray. Applying herbicidal Preparations in the case of aquatic plants are usually carried out by adding the preparations to the aqueous one

20 Medium in the area where control of aquatic plants is desired.

The application of an effective amount of the herbicide preparations according to the invention at the site of the undesirable weeds is essential and critical for the application according to the invention. The one to use The exact amount of active ingredient depends on various factors, e.g. the type of plant and its stage of development, Type and condition of the soil, the amount of rain and the specific acetanilide used. In the case of selective pre-emergence application to plants or soil, an application rate is usually required from 0.02 to 11.2 kg / ha, preferably from about 0.04 to 5.60 kg / ha, or 1.12 to 5.6 kg / ha acetanilide is used.

In some cases larger or smaller quantities may be required. The skilled person can based on the Description, including examples, easily determine the optimal amount for each case.

The term "soil" is used in the broadest sense of the word and includes all common types of soil one as described under "soils" in Webster's New Internationa! Dictionary, Second Edition, Unabridged (1961) are defined. The term refers to any substance or medium in which plants take root and can grow, and includes not only soil, but also compost, manure, dung, humus, and sand Like. One that can sustain plant growth. The compounds of the invention were found to be effective herbicides, particularly as pre-emergence herbicides, although post-emergence activity has also been demonstrated could be. The pre-emergence tests referred to here include both greenhouse and greenhouse tests Field tests. In the greenhouse tests, the herbicide is used either after the seeds or cuttings are planted applied to the surface or incorporated into a certain amount of soil that acts as a top layer over the Test seeds are spread in sown test containers. In the field tests, the herbicide can either be used before the Plants are incorporated into the soil ("P.P.I."), d. i.e. the herbicide is applied to the surface of the earth, then mixed in, then the cultivation seeds are sown, or the herbicide is applied to them Surface applied ("S.A.") after the crop seeds are planted out.

The surface test method ("S.A.") used in the greenhouse is carried out as follows: Container, z. B. aluminum pans with about 24x13x7 cm, or plastic pots with about 9.5x9.5x8 cm, with drainage holes in the soil, are filled to the brim with Ray silt loam, which is then up to a height of 1.3 cm is knocked down below the edge of the pot. The pots are then sown with a plant species to be tested and covered with a 1.3 cm layer of the test soil. The herbicide is then applied e.g. B. with a belt sprayer applied to the earth's surface (187 l / ha, 2.11 bar); each pot then receives 0.64 cm of water from above. then the pots are placed on greenhouse tables and watered from below as required. Another possible one Irrigation from above can also be dispensed with. The assessment of the herbicidal effects

50 takes place about 3 weeks after treatment.

The herbicide treatment by working into the soil (»S.I.«) is carried out in greenhouse tests as follows: Good topsoil is placed in aluminum pans and up to 1 to 1.3 cm below the edge knocked down. A number of seeds or cuttings of various kinds of plants are placed on the earth. The for Complete filling of the pans after sowing or planting soil is necessary in a pan weighed. The earth and a known amount of active ingredient in the form of a solution or suspension of wettable Powders are mixed thoroughly and used to cover the prepared pans. After Treatment, then the pans receive an initial watering from above corresponding to 0.64 cm of rain they are watered from below as needed, so there is adequate moisture for germination and growth is. Irrigation from above can also be omitted. Observation takes place about 2 to 3 weeks after

60 seeds and treatment.

In Tables II and III the results of the tests are compiled which were carried out to the to determine herbicidal yeast activity of the compounds according to the invention; in these tests were the herbicides worked into the soil and watered only from below. Evaluation of herbicidal activity was obtained using a fixed scale based on the percentage of damage to each plant species. the

65 ratings are defined as follows:

10

% Control

valuation

0-24
25- 49
50- 74
75-100
indefinite

The plant species used in a test series for which the data are summarized in Table II, are marked with letters according to the following legend:

A. Canada Thistle Field thistle Cirsium arvense B. Cocklebur Xanthium pensylvanicum C. Velvetleaf Abutilon theophrasti D. Momingglory Winch Ipomoea sp. E. Lambsquarters Report Chenopodium album F. Smartweed Polygonum sp. G Yellow nutsedge Cyperus esculentus H Quackgrass Couch grass Agropyrum repens I. Johnsongrass Sorghum halepense J Downy Brome downy bristle Bromus teciorum K Barnyardgrass Echincchloa crus-galli Table II Pre-emergence test

Verb, from
Example no.

kg / ha

Plant species
ABC

11.2 5.6

11.2 5.6

11.2 5.6

11.2 5.6

11.2 5.6

11.2 5.6

11.2 5.6

11.2 5.6

11.2 5.6

11.2 5.6

11.2 5.6

11.2 5.6

11.2 5.6

5 3 3 3 3 3 3 3 3 3 3 5 2 2 3 3 3 3 3 3 3 3 2 1 1 3 2 2 3 3 3 3 3 3 2 1 3 2 3 0 2 2 3 3 3 1 2 3 3 3 3 3 2 3 3 2 0 2 3 3 2 3 3 1 3 3 5 3 2 3 3 3 3 3 3 3 3 5 2 1 2 3 3 3 3 3 3 3 5 3 2 3 3 3 3 3 3 3 3 5 0 0 3 3 3 3 3 1 3 3 5 2 1 3 3 3 3 3 3 3 3 5 2 0 1 3 3 3 3 3 3 3 3 1 2 2 3 0 2 3 1 3 3 1 0 1 1 3 0 1 3 1 3 3 3 2 0 2 3 3 3 3 3 3 3 3 1 0 3 3 3 3 3 2 3 3 3 2 2 3 3 3 3 3 3 3 3 3 2 1 2 3 3 3 3 1' 3 3 3 2 1 3 3 3 3 3 3 3 3 3 1 1 2 3 3 3 3 0 3 3 3 1 1 3 3 3 3 3 0 3 3 3 1 1 2 3 3 1 3 1 3 3 3 2 0 2 3 3 3 3 0 3 3 3 1 0 2 1 2 3 3 3 3 3 3 2 2 3 3 3 3 3 3 3 3 3 2 2 3 3 3 3 3 2 3 3

45 50

65

The compounds were also tested on the following plant species using the above procedure:

L. Sybean Soybeans Xanthium pensylvanicum M. Sugarbeet Sugar beet Polygonum convulvulus N Wheat wheat Ipomoea sp. O Rice rice Sesbania exaltata P. Sorghum Sorghum Chenopodium album B. Cocklebur Polygonum sp. Q Wild Buckwheat Bindweed knotweed Abutilon theophrasti D. Morningglory Bromus tectorum R. Hemp sesbania Panicum spp. E. Lambsquarters Report Echinochloa crus-galli F. Stnartweed Digitaria sanguinalis C. Velvetleaf J Downy brome downy bristle S. Panicum species K Barnyardgrass T Crabgrass

The results are shown in Table III.

Table III kg / ha Plant species M. N O P. B. Q D. R. E. F. C. J S. K T Pre-emergence test L. 2 3 3 3 0 3 3 3 3 3 2 3 3 3 3 Verb, from 5.6 1 1 1 2 3 0 1 2 2 3 2 0 3 3 3 3 Example no. 1.12 0 1 0 2 1 0 1 0 3 3 3 0 2 3 3 3 1 0.28 0 0 0 0 0 0 0 0 1 1 1 0 0 2 2 3 0.056 0 0 0 0 0 0 0 0 0 1 1 0 0 1 2 2 0.0112 0 3 2 3 3 1 2 3 3 3 3 0 3 3 3 5 5.6 1 3 2 3 2 0 1 3 1 2 2 0 3 3 3 5 1.12 0 2 0 1 1 0 0 1 1 1 0 0 3 3 3 5 2 0.28 0 1 0 0 0 0 0 0 0 0 0 0 1 1 3 5 0.056 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 5 0.0112 0 3 3 3 3 1 3 3 3 3 3 I. 3 3 3 3 5.6 0 1 1 3 3 1 0 3 1 3 0 0 3 3 3 3 1.12 0 0 0 2 2 0 0 0 0 3 0 0 1 3 3 3 3 0,.?, 8 0 0 0 1 0 0 0 0 0 2 3 0 0 3 3 3 0.056 0 0 0 0 0 0 0 0 0 1 0 0 0 3 3 3 0.0112 0 0 0 0 0 0 0 0 0 3 0 0 0 1 0 1 0.0056 0 3 3 3 3 2 3 3 3 3 3 1 3 3 3 3 5.6 2 3 2 3 3 1 3 2 3 3 3 1 3 3 3 3 1.12 1 1 2 2 1 0 1 0 1 3 3 0 2 3 3 3 4th 0.28 0 1 1 1 2 2 1 0 2 1 1 0 0 2 2 3 0.056 0 1 0 0 0 0 0 0 0 1 0 0 0 3 3 3 0.0112 0 2 3 3 3 1 3 3 3 3 3 1 3 3 3 3 5.6 1 2 2 J 3 0 2 0 2 3 3 0 3 3 3 3 1.12 0 2 1 3 3 2 2 3 2 3 3 0 3 3 3 3 5 0.28 0 1 0 1 2 1 2 0 1 3 1 0 2 3 3 3 0.056 0 1 0 0 0 1 1 0 0 3 1 0 1 2 3 3 0.0112 0 3 3 3 3 2 3 3 3 3 3 1 3 3 3 3 5.6 1 1 0 3 3 1 3 3 1 3 3 0 3 3 3 3 1.12 0 2 0 2 2 2 2 1 3 3 3 0 3 3 3 3 6th 0.28 0 2 0 1 2 1 2 2 2 3 1 0 2 3 3 3 0.056 0 2 0 1 0 2 2 2 2 3 1 0 1 1 3 3 0.0112 0

12th

continuation

Verb, from kg / ha plant species

Ex. No. LMNO

5.6 0 3 2 2 3 0 2 2 2 3 0 0 3 3 3 3 i. 1.12 0 1 0 0 1 0 1 0 0 2 0 0 0 2 3 3 0.28 0 0 0 0 0 0 1 2 0 0 0 0 0 2 2 3 0.056 0 1 0 1 0 0 0 0 0 3 2 0 0 0 2 3 5.6 2 3 3 3 3 2 3 3 3 3 3 1 3 3 3 3 2 ( 1.12 1 2 3 3 3 0 2 0 I. 3 3 0 3 3 3 3 0.28 0 1 2 1 2 0 2 0 2 1 1 0 2 3 3 3 0.056 0 0 1 1 1 0 0 0 0 I. 1 0 1 3 3 3 00112 I. 0 Λ 0 f \
\ J 1 0 0 1 0 0 0 i 0 2 3 5.6 2 2 3 3 3 2 3 3 3 2 3 1 3 3 3 3 25th 1.12 1 2 3 3 1 1 3 1 2 2 2 0 3 3 3 3 0.28 1 2 2 3 2 0 1 1 2 1 1 0 3 3 3 3 0.056 0 0 0 0 0 0 0 0 0 2 1 0 2 3 3 3 0.0112 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 3 30th 5.6 3 3 3 3 3 2 3 3 3 3 3 0 3 3 3 3 1.12 1 2 3 3 3 0 3 3 2 2 3 0 3 3 3 3 0.28 0 2 2 2 2 0 1 0 2 3 2 0 3 3 3 3 0.056 0 1 0 1 C. 0 0 0 1 0 0 0 0 3 3 3 0.0112 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 3 35 5.6 0 3 3 3 3 1 3 3 3 3 3 1 3 3 3 5 ', 12 0 3 1 3 1 1 1 2 1 2 2 0 3 3 3 5 0.28 0 2 1 2 1 0 0 0 1 1 1 0 3 3 3 5 0.056 0 1 0 0 0 0 0 0 5 0 0 0 1 2 3 5 40 0.0112 0 1 0 0 0 0 0 0 0 0 0 0 0 1 3 5 5.6 1 2 2 3 3 1 2 2 0 2 1 0 3 3 3 3 1.12 1 2 1 2 3 0 2 2 1 2 2 0 3 3 3 3 0.28 0 1 0 1 0 0 1 0 0 1 0 0 1 2 3 2 0.056 0 5 0 0 0 0 5 0 0 0 0 0 0 0 2 0 5.6 2 3 3 3 3 2 3 3 3 3 3 2 3 3 3 3 1.12 1 2 3 3 3 0 2 2 3 2 3 0 3 3 3 3 0.28 2 2 3 3 1 0 1 0 3 1 3 0 3 3 3 3 0.056 0 1 1 1 0 0 1 0 C. 0 0 0 2 3 3 3 0.0112 0 0 0 0 0 0 0 0 1 5 5 0 0 0 2 2

The herbicides of the invention have been found to have unexpectedly superior properties as pre-emergence herbicides especially for the selective control of difficult to kill perennials and annual weeds, including perennial weeds such as couch grass, yellow and purple sedge (Cyperaceae), annual broad-leaved weeds such as Sida spinosa, Sesbania exaltata, Polygonum sp., Chenopodium album, Amaranthus and annual grasses such as Sorghum bicolor, Brachiaria plantaginea, Sorghum halepense, Panicum texanum, Panicum miliaceum, Oryza sativa, Rottboellia exaltata, foxtails (e.g. Setaria veridis, lutescens and faberi), Echinochloa crus-galli and Digitaria sanguinalis. Also with other resister.ten Species a reduction in weed populations has been achieved, e.g. B. in Ambrosiaceae, Abutilon theophrasti, Ipomoea sp., Xanthium pensylvanicum, Portulac.

Selective control and increased suppression of the above-mentioned weeds with the aid of the invention Herbicide has been found in a wide variety of crops of useful plants, some of which are of particular interest Interest corn and soybeans, but also others such as cotton, peanuts, rapeseed, French beans, wheat and sorghum; these last two crops are usually less tolerant of those of the invention Herbicides as other of the crop plants mentioned; this reduced tolerance can be achieved by using of protective agents, e.g. B. herbicidal antidotes are improved.

In the following discussion of the data, reference will be made to herbicide application rates represented by "GR, 5" and "GR _g5 "; these quantities are given in kg / ha.

GR _{] 5} defines the maximum amount of herbicide that will cause damage to 15% or less of the crops, while GR _{85 is} the minimum amount necessary to achieve 85% weed inhibition. The GR15 and GR ₈₅ quantities are used as a measure of the possible performance of commercially available products, although suitable commercially available herbicides can of course have greater or lesser damage to plants within reasonable limits.

Another indication of the effectiveness of a chemical as a selective herbicide is the “selectivity factor” (“SF”) for a herbicide on certain crops and weeds. It is a measure of the relative

Degree of harmlessness to crops and harmfulness to weeds, and is called the ratio GR | _5/85 expressed GR, ie GR, ₅ quantity for the crop divided by the quantity GR ₈₅ for the weed, both quantities in kg / ha. In the tables below, the selectivity factors are given in brackets after the GR ₈₅ amount for each weed; "NS" means "non-selective"; insignificant or indeterminate selectivity is indicated with a dash (-).

Since crop tolerance and weed control are related, there is a brief discussion this ratio, expressed as the selectivity factor, is appropriate. In general, it is desirable that the Harmfulness factors for the crop, d. H. the herbicide tolerance values of the crop are high, because, for one reason or another, higher herbicide concentrations are often desired. Vice versa should limit the amounts for weed control for economic and possibly ecological reasons be small, d. that is, the herbicide should have a high unit activity. Small application rates of a herbicide however, they may not be sufficient to control certain weeds, and a greater amount will be needed. The best herbicides are therefore those that have the greatest number with the lowest application rate control of weeds and the greatest possible harmlessness for the crop, d. H. Crop tolerance, Offer. The selectivity factors (defined above) are thus used to calculate the relationship between To quantify the harmlessness to the crop and control of the weeds. For those in the The following applies to the selectivity factors given in the tables: the higher the numerical value, the greater the selectivity of the herbicide for weed control in a given crop.

To the unexpectedly superior properties of the compounds according to the invention both on absolute as well as on a relative basis, comparative tests with known compounds were carried out in the greenhouse carried out, which in their chemical structure most closely related to the compounds according to the invention are. These known compounds are identified as follows (using the same nomenclature as for the compounds according to the invention used):

A. N-methoxyethyl ^ '- trifluoromethyl ^ -chloroacetanilide.

B. N- (ethoxyethyl) -2'-trifluoromethyl-2-chloroacetanilide.

Tables IV and V summarize data for the pre-emergence herbicidal activity with which the relative effectiveness of the compounds according to the invention and the known compounds as selective Herbicides against the resistant and annoying perennial weeds couch grass and Cyperus esculentus in Soybeans and corn are compared. These weeds usually go with such larger crops as Corn and soybeans go hand in hand. The test data in Tables IV and V were made under identical conditions and represent the average of 2 runs (excluding compound of Example 13, the was only used in a comparative test). The test procedure was the same as for Tables II and III, one modification consisted of an initial irrigation from above that received 0.64 cm of rain corresponded to; the subsequent irrigation took place from below. "NS" means non-selective within the test limits.

Table IV URiä crowd GRgs set Cyperus esculentus link (kg / ha) (kg / ha) 1.13 (1.98) Soybeans Couch grass 0.44 (4.45) > 2.24 > 2.39 (NS) 0.17 (15.6) A. 1.96 0.61 (3.21) 0.19 (8.84) B. 2.67 0.17 (15.6) 0.17 (6.59) Example 1 1.68 0.27 (6.22) 0.26 (5.62) Example 3 1.12 0.13 (8.62) 0.17 (12.53) Example 4 1.46 0.26 (5.62) Example 5 2.13 0.20 (10.65) Example 13

From Table IV it can be seen that each compound of the invention was effective against both couch grass and Cyperus esculentus showed significantly higher selectivity factors (values in brackets) in soybeans than known connections. In particular, it should be noted that the unit activities (relative phytotoxicity per herbicide unit) of the compound according to the invention was noticeably higher than that of couch grass and Cyperus esculentus, as those of the known compounds, while harmless to crops remained. The extraordinarily high selectivity factors of the compounds are particularly noteworthy of Examples 1 and 13.

Further comparative data showing the effectiveness of the compounds according to the invention in comparison to the The above known compounds against couch grass and Cyperus esculentus in maize are in

(i5 Table V compiled.

14th

CiR ^ quantity 31 10 523 Cyperus esculentus Table V (kg / ha) 1.13 (1.98) link Corn (iRxs quantity 0.44 (1.84) > 2.24 (kg / ha) 0.17 (4.47) 0.81 Couch grass 0.19 (10.2) A. 0.76 > 2.39 (NS) 0.17 (4.47) B. 1.94 0.61 (1.33) 0.26 (7.04) Example 1 0.76 0.17 (4.47) 0.17 (13.18) Example 3 1.83 0.27 (7.19) Example 4 2.24 0.13 (5.85) Example 5 0.26 (7.04) Example 13 0.20 (11.2)

From Table V it can be seen that each compound of the invention has significantly higher selectivity factors compared to couch grass and Cyperus esculentus in maize as the known compounds. Again it can be seen that that the unit activities of the compounds according to the invention against couch grass and Cyperus esculentus were noticeably higher than those of the known compounds, while the harmlessness for the culture was preserved. Particular attention should be paid to the high selectivity factors for the connections of Examples 3, 5 and 13, especially in comparison with those of the known compounds.

From the comparison data in Tables IV and V it can be seen that the compounds according to the invention extraordinarily higher and unexpectedly superior herbicidal effectiveness compared to the resistant perennial Weeds couch grass and Cyperus esculentus in two main crops, i.e. H. Soybeans and corn, showed than compounds A and B, which are the most closely related of the known compounds.

Data from further pre-emergence tests also showed that the compounds according to the invention also contain couch grass, Cyperus esculentus and / or other weeds in one or more crops of cotton, peanuts, Selectively control French beans, wheat, sorghum and / or rapeseed. In Table VI are e.g. B. data compiled, which the herbicidal selectivity of the compounds of Example 1 and 3 against couch grass in Show rapeseed, French beans, sorghum and wheat. Unless otherwise noted, it was used for the greenhouse testing of Table VI and other tables incorporated the herbicide into the soil, and after an initial Watering from above was watering from below, as described above.

Table VI

link

GR | 5 amount (kg / ha)

Rapeseed

French beans

Sorghum

GR ₈₅ quantity
(kg / ha)

wheat

Couch grass

Example 1

Example 3

0.86

1.9

0.90

2.24

0.24

0.84

0.12 (7.2)

0.12 (7.5)

0.12 (2.0)

0.12 (1.8)

0.28 (6.8)

0.28 (8.0)

0.28 (3.0)

0.28 (1.0)

The compound of Example 1 was also tested in the field for its pre-emergence selectivity over against Foxtail species, Echinochloa crus-galli and Panicum miliaceum can be identified in several cultures. The data (obtained from three runs) are in Table VII for both surface application (S.A.) as well as for incorporation into the soil (PPI, i.e. incorporation before planting) of the herbicide. The seeds were placed in a fine seedbed of silt loam with medium moisture at a depth of 5.08 cm planted. The first rain (0.51 cm) fell the day after treatment, the second rain (0.64 cm) two Days after treatment; the total amount of rain 22 days after treatment was 4.57 cm. The appraisal occurred 6 weeks after treatment.

Table VII

link

Application method

lot 7c inhibition cutie pie soy Earth tree Sorghum bush Rapeseed Fox- Echi- Panicum OJ (kg / ha) Field Corn beans nuts wool beans tail- nochloa miliaceum H-" muis specics (- '
O 0 0 0 0 0 0 0 62 63 63 to 0.56 13th 0 5 0 13th 3 8th 0 92 93 83 1.12 I) 7th 0 8th 20th 17th 20th 5 93 93 95 2.24 0 27 13th 22nd 25th 77 32 33 98 98 97 4.48 15th 0 5 17th 13th 32 23 0 75 75 23 0.56 0 3 7th 13th 32 53 10 0 90 93 58 U2 (I. 27 20th 15th 37 92 37 15th 98 98 80 2.24 <; 40 40 28 82 98 43 40 100 100 85 4.48 32

Ex. 1 S.A.

P.P.I.

Table VII shows that the compound of Example 1 generally performed better as a selective herbicide, when applied to the surface as if it was incorporated into the ground. In the surface tests the herbicide selectively controlled the three tested weeds at application rates 0.58 kg / ha, while up to 4.48 kg / ha remained harmless for the cultivated plants field maize and soybeans (i.e., up to about 15% maximum damage); sweet corn, peanuts and rapeseed remained harmless until at over 2.24 kg / ha, for cotton, sorghum and French beans it was just under 2.24 kg / ha. In the PPI testing controlled the compound of Example 1 selectively for foxtail species and Echinochloa crusgalli with less than 1.12 kg / ha, while the harmlessness for field maize, peanuts and rapeseed is up to to 2.24 kg / ha, and itir soybeans were retained at amounts just under 2.24 kg / ha.

Further field test data for the compound of Example 1 showed selective pre-emergence control of other weeds in soybeans, corn, cotton and / or peanuts; these included purple sedge, Setaria faberi and lutescens, Melde, Ipomoea, Xanthium pensylvanicum, Abutilon theophrasti, Polygonum pensylvanicum, Sida spinosa, Portulac, Digitaria sanguinalis, Bedstraw, Panicum texanthum / Richardia scabidum and. Of course, not all of the weeds mentioned can be selectively controlled in all of the crops mentioned under all climatic, soil, moisture and / or application conditions. Selectivity data for the control of the above weeds in soybeans, corn, cotton and peanuts from a variety of field tests in different locations under different conditions of soil, humidity, etc. are listed together in Tables VIII through XI. In the tables, “WAT” means “weeks after treatment” of the plants with the herbicide, which is either applied to the surface (“SA”) or worked into the soil before planting (“PPI”); the application rate for each crop / weed combination is given as GR _{] 5} or GR ₈₅ amount (as defined above). The GR | j / GR ₈ 5 ratio gives the selectivity factor »SF«; "NS" means non-selective, and a dash (-) indicates insignificant or indeterminate selectivity, e.g. B. because the actual GR | ₅ - ₈ and GR j levels higher or lower than the maximum or minimum amounts were used in the 'eweiligen test. In Tables VIII through XI, a vacancy means that the plant species was not present in a particular test plot, or that the data was not obtained, or that it was less significant than other available data, e.g. B. some 3 WAT observations were dropped in favor of 6 WAT data, or 6 WAT data were left out because the 3 WAT data were definitive.

Table VIII To whom
manic
procedure WAT GR | ₅ / GRs5 S.F. Connection crops /
Weed-
combination S.A. 3
5 > 4.48 / <1.12 (> 4.0) Example 1 soybeans /
Setaria faberi P.P.I. 3
5
8th > 4.48 / <1.12
> 4.48 / <1.12 (> 4.0)
(> 4.0) S.A. 6th 2.52 / 2.8 (NS) Soybeans /
Setaria lutescens P.P.I. 6th 1.4 / <1.12 (> 1.3) S.A. 6th 2.52 / 2.52 (1.0) Soybeans /
Report P.P.I. 6th 1.4 / 2.8 (NS) P.P.I. 8th 4.48 / 2.52 (1.8) Soybeans /
Polygonum
pensylvanicum

The data in Table VIII show that the compound of Example 1 selectively selectively Setaria lutescens and faberi, Melde and Polygonum pensylvanicum in soybeans from 6 to 8 WAT using either the S.A. or the P.P.I. process controlled.

Table IX Cultivated Plants /
Weed-
combination To whom
manic
procedure WAT GR1 ₅ / GR ₈₅ S.F. link Corn/
Setaria faberi SA
SA 6th
6.5 4.48 / <1.12
> 7.84 / 8.4 (4.0)
(NS) Example 1

continuation

Link crops / weeds combination

To whom-

manic

procedure

WAT

SF.

PPI
PPI 6th
6.5 4.76 / 1.96
> 6.72 / 4.48 SA
SA 3
6th > 4.48 /> 4.48
> 4.48 /> 4.48 PPI
PPI 3
6th 4.76 /> 4.48
4.76 /> 4.48 SA
SA 3
6th > 4.48 /> 4.48
> 4.48 /> 4.48 PPI
PPI 3
6th 4.76 /> 4.48
4.76 /> 4.48

(2.5) (1.5)

Corn / Ipomoea

Corn/

Xanthium

pensylvanicum

The data in Table IX show that the compound of Example 1 selectively produced Setaria faberi in maize from 6 to 6.5 WAT controlled with either the S.A. or the P.P.I. process; the selectivity of Ipomoea and Xanthium pensylvanicum was indeterminate in the test levels, however the repression of these plants was shown.

Table X

link

Cultivated plants / weeds combination

Application method

WAT

GR, ₅ / GR ₈₅

S. F.

Example 1 cotton /

purple sedge

Cotton / Sida spinosa

Cotton / purslane

Cotton/

Digitaria

(straight or hairy)

Cotton / bedstraw

P.P.I.

3.64 / 1.68 3.36 / 2.24

3.30 / 4.2

3.64 / 3.08 3.36 / 4.76

3.36 / 4.76 3.36 / 1.96

0.84 / 1.12 0.84 / <1.12

(2.17)

(1.5)

(NS)

(1.18) (NS)

(NS) (1.7)

Ol, 25) (NS)

Table X shows that the compound of Example 1 selectively selects up to purple sedge and purslane 9 WAT, Sida spinosa up to 6 WAT and Digitaria up to 7 WAT controlled; was the control of bedstraw insignificant or indefinite.

Table XI contains data on the pre-emergence activity of the compound of Example 1 against three resistant ones annual weeds, d. H. Panicum texanum, Acanthospermum hispidum and Richardia scabra in peanuts for periods up to 12 WAT. The data in Table XI represent the average of 3 runs in sandy loam containing 1.3% organics, 79.2% sand and 10% clay; the herbicide was on the Surface applied.

lot % Inhibition 12th 31 10 523 8th 12th Acanihospermum h. 12th Richardia se. 8th 12th Table XI (kg / ha) peanuts 0 67 40 WAT 40 WAT 90 Ver WAT 0 63 55 4 8 60 4th binding 4 8 0 Panicum tcxanum 88 78 78 100 0 95 95 2.24 5 O WAT 85 0 3.36 10 0 4th 95 0 Example 3 4.48 17 7 50 68 85

The data in Table XI show that the compound of Example 1 was selective to Texas panicum in peanuts controlled for 8 weeks, and showed a high degree of control even at 12 WAT at 4.48 kg / ha; selective Control of Acanthospermum h. was achieved with 3.36 kg / ha for 8 weeks, and complete control was obtained right for 12 WAT with 4.48 kg / ha; selective control of Richai dia se. was with less than 2.24 kg / ha for 8 WAT and 4.48 kg / ha gave 95% control at 12 WAT.

In further greenhouse tests, compounds according to the invention showed selective control of a large number of annual and perennial weeds in various crops. For example, the compound of Example 1 selectively controlled purple sedge in both corn and soybeans, and the corresponding crop / weed GR | ₅ / GR ₈ 5 ratios (expressed in kg / ha) were 0.67 / 0.25 (SF = 2.7) in maize and 1.12 / 0.25 (SF = 4.5) in soybeans. The compound of Example 11 showed selective control of yellow sedge and couch grass in corn and soybeans. The culture / sedge GR | ₅ / GR ₈₅ ratios were> 2.24 / 0.95 (SF = 2.4) in corn; 2.24 / 0.5 (SF = 4.5) in soybeans and the corresponding GR, ₅ / GR ₈₅ ratios for maize and soybeans in couch grass were> 2.24 / 0.5 (SF => 4, 5). In a test against yellow sedge in cotton, the GR was | ₅ / GR ₈₅ ratio (average of 2 passes) 1.96 / 0.95 (SF = 2.1). The compound of Example 13 showed equally selective control of yellow sedge in cotton and of couch grass in wheat, the respective GRi ₅ / GR _g5 ratios were 0.7 / 0.47 (SF = 1.7) in cotton and 0.58 / 0.47 (SF = 1.2) in wheat.

The compounds of Examples 1, 13, 14 and 15 were tested against yellow sedge in cotton, soybeans, maize and rice in a multi-culture test in the greenhouse; none of the compounds were selective with respect to yellow sedge in rice. However, clearly high selectivities for yellow sedge in cotton, soybeans and corn were found for each of the compounds tested; the respective GR, ₅ and GR ₈₅ amounts for these compounds are listed in Table XII; the selectivity factors are in brackets after each crop.

Table XII

link

GR ₈₅ (kg / ha)

yellow sedge

cotton

GR ₁₅

(kg / ha)

Soybeans

Corn

Example 1 0.24 1.96 (8.2) 0.87 (3.6) 0.69 (2.9) Example 13 0.21 2.52 (12.0) 1.96 (9.3) 2.52 (12.0) Example 14 0.38 2.8 (7.4) 2.24 (5.9) 1.68 (4.4) Example 15 0.44 2.8 (6.4) 1.96 (4.5) 1.96 (4.5)

The compounds of Examples 1 and 13-15 were also tested against couch grass in wheat, soybeans and corn tested; each of the compounds was found to be non-selective in wheat. The selectivity data for the above Compounds against couch grass in soybeans and corn are summarized in Table XIII.

Table XIII

link

GR ₈₅ (kg / ha)

Couch grass

(kg / ha)
Soybeans

Corn

Example 1 0.07 Example 13 0.36 Example 14 0.45 Example 15 0.75

0.81 (11.6) 0.69 (9.9) 1.68 (4.7) 1.68 (4.7) 1.46 (3.2) 2.52 (5.6) 1.96 (2.6) 2.24 (3.0)

In further greenhouse tests, the compounds of Examples 1 and 3 were tested for their herbicidal activity tested against a number of annual grasses; this includes resistant weeds such as Panicum texanum, Sorghum haJepense seedlings, Sorghum bicolor, Brachiaria plantaginea, Panicum mileaceum, Oryza sativa and Rottboellia exaltata. The results of these tests are shown in Table XIV; the selectivity factors appear in brackets; The dash (-) indicates insignificant or indefinite selectivity at.

Table XIV

Ver GR | 5 quantity Panicum Sorghum Sorghum GR _g5 amount P. milia- Autumn- Oryza Rott binding (kg / ha) texanum H. b. (kg / ha) ceum panicum sativa boeüia soy 1.12 0.14 0.28 Bra- 1.12 <0.07 0.2 1.12 15th beans 01.0) (> 8.0) 04.0) charia 6> l, 0) 016.0) O5.6) Oi, 0) Example 1 > 1.12 > 1.12 0.28 0.93 0.56 1.12 <0.07 0.14 > 1.12 (-) 04.0) OU) 02.0) (-) 016.0) 08.0) (-) 20th Example 3 > 1.12 > 1.12 01.0)

Table XIV shows that the compound of Example 1 was selective for every annual weed tested in soybeans controlled. The compound of Example 3 showed positive selective control against all weeds, except for Panicum texanum, Panicum miliaceum and Rottboellia at the maximum test amount of 1.12 kg / ha; a higher amount would have been necessary in order to increase the selectivity of the compound over these identify three weeds.

One particular advantage of a herbicide is its ability to act on a variety of soil types. In Table XV summarizes data showing the herbicidal effectiveness of the compound of Example 1 Mercury in soybeans present in a variety of soil types that contain various proportions of organic Contains fabrics and clay. Herbicidal treatments were done by working into the soil, the seeds were planted 0.95 cm deep and received 0.64 cm watering from above. The observations were made about

35 3 weeks after treatment. The selectivity factors are given in brackets.

Table XV

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Soil type

ORGANIC SUBSTANCES

volume

GR | 5 quantity GR ₈₅ quantity
(kg / ha) (kg / ha)

Soybean couch grass

⁴⁵ Example 1

Ray silt loam 1.0 9.6 - 1.12 0.22 (5.1) Sarpy silty clay 2.3 30.35 > 2.24 0.28 (> 8.0) Wabash silty clay 4.3 33.0 - 0.28 (-) Drummer silty tone 6.0 37.0 2.24 0.11 (20.0) Florida sand 6.8 1.8 1.96 0.2 (9.8) Florida peat peat 60 > 2.24 0.58 (> 3.9)

Table XV shows that the compound of Example 1 compared to soil types with different proportions seems to be quite insensitive to organic substances; it showed selective control of couch grass in soybeans in soils that have an organic content of 1.0% to 60% and a clay content of at least 1.8% to about 37%. The door soybean in Wabash silty clay data was indeterminate in this test. The selectivity values given for Sarpy and Drummer silty clay as well as Florida peat soil are minimum values, since the maximum test amount was 2.24 kg / ha and the herbicide for soybeans was included the same amount over 2.24 kg / ha was harmless.

Laboratory tests have been carried out to determine the leaching resistance of the herbicides of the invention in the soil and the resulting herbicidal effectiveness. In these tests, the Compounds of Examples 1 and 4 to 6 dissolved in acetone and then in various concentrations to one weighed amount of Ray silt loam and drummer sprayed silty clay loam that was contained in pots, the drainage holes in the bottom of the pot were covered with filter paper. The pots with the treated soil were

20th

the leached out by placing them on a turntable under two nozzles of a water container rotated; these were set so that they gave off 2.5 cm of water per hour and thus simulated rain. the Leach rates were adjusted by changing the time on the turntable. That on the floor in Water added to the pot was allowed to pass through the filter paper and the drainage holes. Then they stayed Stand pots at room temperature for 3 days. The treated soil was then removed from the pots, crumbled and given as a surface layer on other pots with the same soil in which Echinochloa seeds are already in place were sown. The pots were then placed on greenhouse tables, watered from below and 2 bis Left to grow for 3 weeks. The visual rating of the percent growth inhibition was made compared with untreated control pots, as well as the fresh weights of Epinochloa; the data for the Controls were obtained from 6 runs, those for the 3-run test compounds; the data are compiled in Table XVI. The fresh weight of the weeds was not used for the Drummer tests measured in silty clay.

Table XVI

Compound amount of rain

(kg / ha) (cm)

control

Ex.

Example 4

Example 5

2.24

0.56

0.14

2.24

0.56

η u

2.24

0.56

0.14

1.27

5.08

10.16

1.27

5.08

ϊΰ, ιό

1.27

5.08

10.16

1.27

5.08

10.16

1.27

5.08

10.16

1.27

5.08

10.16

ϊ, 27

5.08

10.16

1.27

5.08

10.16

1.27

5.08

10.16

1.27

5.08

10.61

Echinochloa crus-galli Fresh weight (g) 0 ':(. Inhibition Ray drummer 0 Ray Drummer Schlufllehm SchlulTton 0.20 Scbluff clay Silt tone 4.37 2.65 3.88 0 4.14 0 3.98 1.21 A vg. 4.10 2.73 0.20 100 100 0.17 100 100 1.74 95 100 3.26 35 100 0 100 100 0 100 100 0 70 100 0.22 33 100 0 95 100 0 96 97 0.24 58 95 1.97 20th 20th 0.05 100 100 0.22 100 100 1.53 100 100 3.15 95 100 0 100 100 0 100 100 0.31 94 100 1.18 52 100 0.02 99 8th! 0 95 99 0.44 63 94 3.41 14th 54 0 100 100 0.41 100 100 2.77 92 100 3.62 71 100 99 100 100 100 89 100 17th 96 98 70 90 96 38 85 12th 47

continuation

Compound amount of rain

(kg / ha) (cm)

Ex. 6 0.24

0.56

0.14

5.08

10.16

5.08

10.16

1.27

5.08

10.16

Echinochloa crus-galli Fresh weight (g) % Inhibition Ray drummer Ray Drummer Silt loam silt clay SchlufTlehm Silt tone 0 100 100 0 100 100 0.03 99 100 0.64 84 100 0.04 99 50 0.02 99 100 0.41 90 93 1.17 72 84 0.66 84 12th 0.43 90 26th 1.72 58 20th 2.92 29 12th

Table XVI shows that the compounds according to the invention under various precipitation conditions were fairly resistant to leaching in the soil. In particular, each of the invention controlled Compounds at the 2.24 kg / ha application rate Echinochloa below the equivalent of 10.16 cm precipitation in Ray SchlufTlehm and Drummer Schiufftonlehm, excluding the connections of Examples 1 and 5 in Ray Schluff, where control is upright under an equivalent of 5.08 cm of rainfall was obtained. Even at the low application rate of 0.14 kg / ha, the compounds controlled the Examples 1, 4 and 5 Echinochloa in Drummer silty clay loam under an equivalent of two inches Precipitation.

Toxicological studies of the compound of Example 1 indicated that the compound was fairly harmless. It is slightly toxic (OLD ₅₁ , 2300 mg / kg; MLD ₅₀ > 5010 mg / kg), it causes slight eye irritation, but no skin irritation. Special handling measures beyond the normal precautionary measures are not considered necessary.

From the preceding detailed description it can be seen that the compounds according to the invention exhibited unexpected and extraordinarily superior herbicidal properties, both absolutely as well as in comparison to the structurally most closely related known compounds. In particular The compounds according to the invention proved to be outstandingly selective herbicides, especially in the Control of difficult-to-kill perennial and annual grasses in soybeans and maize, but also in Peanuts, cotton and other crops. Above all, the compounds according to the invention showed excellent results Control of perennial weeds such as couch grass and sedge as well as resistant annual grasses such as Panicum texanum, Rottboellia, Panicum miliaceum, Brachiaria plantaginaria, Sorghum halepense seedlings, Sorghum bicolor and / or Oryza sativa, while they are also less resistant annual grasses and controlled and / or pushed back perennial weeds.

Claims (1)

Claims: 1. 2'-Trifluoromethyl-2-chloroacetanilide of the general formula ClCH ₂ C CH ₂ OR where mean: either R, hydrogen and R isopropyl or R, methyl and RC ₁ -., - alkyl, alkoxyalkyl, alkenyl or alkynyl with up to 5 carbon atoms
or R, ethyl and R ethyl, n-propyl or isopropyl.
2. N-iEthoxymethyO ^ '- trifluoromethyl-o'-methyJ ^ -chloroacetanilide. 3. N-Cn-PropoxymethyO ^ '- trifluoromethyl-o'-methyl ^ -chloroacetanilide. 4. N-ilsopropoxymethylW-trifluoromethyl-o'-methyl ^ -chloroacetanilide. 5. N-dsobutoxymethyD ^ '- trifluoromethyl-o -'-methyl ^ -chloroacetanilide. 6. N-CEthoxymethyD ^ '- trifluoromethyl-o'-ethyl ^ -chloroacetanilide. 25 7. N-yne-PropoxymethyO ^ '- trifluoromethyl-o'-ethyl ^ -chloroacetanilide. 8. N-UsopropoxymethylH'-trifluoromethyl-o'-ethyl ^ -chloroacetanilide. 9. N-isopropoxymethyD ^ '- trifluoromethyl ^ -chloroacetanilide. 10. N-lallyloxymethylH'-trinuomethyl-o'-methyl ^ -chloroacetanilide. 11. N-iPropargyloxymethyD ^ '- trifluoromethyl-o'-methyl ^ -chloroacetanilide. 50 12. N- (2-Methoxyethoxymethyl) -2'-trinuomethyl-6'-methyl-2-chloroacetanilide. 13. Herbicide to control unwanted plants in crops of useful plants, especially in maize crops, Soybean crops, cotton crops, rapeseed crops and French bean crops containing at least a 2'-trifluoromethyl-2-chloroacetani] id according to claims 1 to 12 in a herbicidally effective amount and at least one common additive.