CS195700B2 - Herbicide - Google Patents

Description

The present invention relates to novel herbicidal compositions containing ring-substituted N- (2,2-difluoroalkanoyl) -o-phenylenediamines.

The control of animal parasites is one of the oldest and most important problems of animal production. Many types of parasites affect all animal species. The vast majority of animals are affected by free-flying parasites such as flies, crawling ectoparasites such as lice and aphids, drilling parasites such as larvae and flyworms, and microscopic endoparasites such as coccidia, as well as larger endoparasites such as worms. Thus, control of parasites in a single host is a complex problem with many side problems.

Insect and mite parasites that eat live tissues from host animals are harmful. This group includes parasites of all economic animals including ruminants and single-stomach mammals and poultry and companion animals such as dogs.

Recently, many methods for controlling these parasites have been tested. The Cochlimyia hominivorax flies were practically exterminated in Florida by the release of a large number of sterile male flies.

Of course, the method is applied only in an easily insulated area. The free-flying insects are usually controlled by conventional methods such as free-dispersed air and contact insecticide) and fly traps. Skin-crawling crawling parasites are usually controlled by dipping, soaking or spraying the animals. with suitable parasiticidal agents. 'J'

Some progress has been made in the systematic control of some parasites, particularly those living in or migrating in the host animal. Systemic control of animal parasites was performed by absorption of the parasiticidal agent in the bloodstream or other tissue of the host animal. Parasites that eat or come into contact with the tissue containing the parasiticidal agent are killed by either ingesting or coming into contact with the parasiticidal agent. Some phosphate, phosphoramidate and phosphorothioate insecticides and acaricides have been found to be sufficiently non-toxic and can be used systemically in animals.

Rumanowski, U.S. Patent 3,557,211 discloses uvádí, Ν-bis (acetyl) -o-eryllenediamines which are useful for controlling plants, insects and fungi.

The present invention relates to a herbicidal composition which contains as active ingredient

on the ring, the substituted N - (2,2-fluoro-alkanoic-phenylenediamine) of the formula ΠΙ,

O

-Č-C £

-R 1 (III) wherein

R ² is a trifluoroacetyl or furoyl,

R ^e is methylsulfonyl and is located at the 4 or 5 position.

All compounds of formula III may be formulated as being useful as herbicides. These compounds can be used in such a way that a broad herbicidal effect is obtained; thus, in the broadest sense, the invention relates to a method of application which is characterized in that a plant inhalation, such as a stem, leaves, flowers, fruits, roots or seeds, or similar reproductive units of plants, is applied with growth inhaling amounts of one of the on the ring substituted N- (2,2-difluoroalkanoyl) -O-phenylenediamines of formula III, however, these compounds can also be used by utilizing selective -herbicidal activity. If a mixture is used, the amount of each individual compound may be reduced so that the mixture exhibits only the desired herbicidal effect.

It is not critical to the herbicidal utility of the compounds whether undesirable vegetation is completely eliminated; Especially with respect to the selective effect, inhibition of not complete killing is sufficient, especially when combined with natural conditions such as limited humidity, which has the most adverse effect on the vegetation. vegetation selectively inhibited than on the useful plants.

The compounds of formula III are also suitable for various variations of herbicidal applications.

Thus, for example, in the case of those which induce the selective effect of the compounds, the amounts are more particularly defined below: "The compounds can be used as / selective herbicides in useful plants, such as, for example, sorghum, sorghum, or sorghum soybean. Three of these applications can be carried out prior to the emergence of the 6Up crop and the weeds, or preferably by direct spraying after the emergence of the crop plants, both before and after the weed.

Three other applications, Tzoro Til compounds can be used to provide a broad herhicidal effect on non-sown soil including un-sown bands of contour from agricultural soil. For such use on so-called cold soil, the application is carried out in spring so as to suppress vegetation growth until autumn or the following spring sowing, or in autumn to suppress vegetation growth until spring or the following autumn sowing. . Further, in another application, the compounds can be used to control weeds in planting utility trees, such as planting various citrus trees. In all of these various applications and others for which the compounds are suitable, the additional advantage is that the compounds must be added to the soil or else mechanically mixed with the soil. In addition to the previous soil treatment applications, the compounds of the invention may also be used as aqueous herbicides.

Desire! The compounds of formula vzorceΠ as herbicides can be carried out, for example, with unmodified compounds, but for good results it is generally necessary that the compounds be used in modified form, i.e. as one component of the compositions adapted to achieve a plant growth inhibitory effect. For example, the active agent may be mixed with water or other liquid or liquids, preferably using surfactants. The active agent may also be combined with a finely divided solid, which may be a surfactant, to provide a wettable powder that may be dispersed in water or other liquid, or the active agent may form part of a dusting agent which is applied directly. Other methods of preparation known from the literature can be used for the use of these compounds.

The exact amount of active ingredient used in the formulation is not critical and varies depending on the type of effect desired, inhibiting the growth, the type of plant in question, the type of active ingredient and the weather conditions. In general, the broad effect of growth inhibition is obtained with amounts ranging up to 22 kg / kg of active ingredient per aktactact and these amounts are suitable for effective control of vegetative growth on icy soil. If a selective weed inhibitory effect is needed in the sowed crop plant area, such as maize, soybean and bavaria, it provides an amount of from 10 to 11.1 kg per hectare in general. Where the active substance is used in the form of a mixture containing the active agent for the agalication, the precise concentration of the active substance in the mixture containing the active substance is not critical, except that conoanthation and the total amount used must correspond to the corresponding amount of active substance. A hectare is generally good when the active ingredient is used at a concentration of < 0.5% or more in the case of a preparation and at a concentration of 1.0 to 5.0%. or higher in the case of dusts, powders, granules and other dry preparations. íKtrn..centrovanější preparations _with m & ho also be prepared and are often preferred prníqže Mehmet serve in their addiction has contemplated «apli5 jfead ® (SNA respective konGentnaCí • How konoeuteované qpreparfity φβο íúčsly: zašříáiií and storage," as .zúkladul mixtures tuse treatment For example, the preparations often, preferably, contain a surfactant and an active ingredient according to the invention, the latter being present in an amount of from 0.5 to 99.5% tactile, having an inert finely divided solid and the active ingredient according to the invention. The present formulation is present in an amount of from 1.0 to 99% by weight. These preparations, as mentioned, can be used directly in certain applications, but can be diluted and then used in many other applications.

Liquid mixtures containing the desired. an amount of active ingredient is prepared by dissolving the compound in an organic liquid or dispersing the compound in water with or without. with a suitable surfactant dispersing agent. These mixtures can also contain modifying compounds which serve to "spread" and "improve" certain plants. Suitable organic liquid carriers for the ijson agricultural oil and petroleum oils, such as diesel fuel, oil, fuel oil and Stoddard solvent. Among these liquids, distillates are generally preferred. The aqueous mixtures may contain one or more miscible water-immiscible solvents for the toxic compound. In such compositions, the carrier comprises an aqueous emulsion, for example, a mixture of water, an emulsifying agent, and a solvent which is non-aqueous with water. formation of the desired mixture. Dispersants and emulsifiers that can be used in mixtures include the condensation products of alkylene oxides with phenols and organic acids, alkyl arylsulfonates, polyoxyalkylene derivatives, sorbitan esters, and complex ether alcohols. Examples of surfactants which are suitably used in the practice of the invention are set forth in U.S. Patents 3,095,299, second column, lines 25-36, and No. 2,655,447, column 5, and No. 412,510, column 4; 5.

In the preparation of dusts, the active compounds of formula III are intimately mixed with or applied to finely divided solids such as clay, talc, chalk, gypsum, limestone, vermiculite or perlite.

According to one method of preparing this dispersion, the finely divided carrier is mechanically mixed or milled with the active compound.

Similarly, dusts containing toxic compounds can be prepared with a variety of solid, surface-active agents such as bentonite, fuller clay, attapulgite and other clays. Depending on the component ratios, the dusts may be used as concentrates and then diluted with other solid surfactant dispersants or chalk, talc. gypsum, and the desired amount of the active compound in the composition adapted for use in plant growth is obtained. These dusts can also be dispersed in water without using dispersants to form a spray mixture.

Preparations containing the active compounds of the formula. Often, it is advantageously modified to admix a number of surfactants which allow for the dispersion and spreading of the pre-parathy on the surface of the plant leaf and its incorporation into the crevice.

The active agent may be dispersed ^In .půdě or v. Other growth medium Jibovnlným manner. Applications can be carried out simply by mixing with the medium. application to the surface of the soil and then plowing or drilling into the soil at the desired depth or using liquid carriers to achieve penetration and impregnation. The application of sprays and dusts on the surface of soil or part of plants or on plant surfaces above the soil can be carried out by any conventional method, for example, sprayers, hand sprayers and sprayed air-driven sprayers.

Although common application methods may be used, they are not required. The advantage of the nnsBEne UI compounds is that they are active and effective as herbicides, once they are merely a rumble on the soil surface, without the need for a further step that facilitates the process. apply only to the surface, apply it to the surface and then apply it to the soil.

. The spreading of the active ingredient in the soil can also be accomplished by adding the composition to the water used to irrigate the soil. In these procedures, the amount of water varies depending on the porosity of the soil and the soil retention capacity of the soil so as to achieve the desired degree of agent distribution.

Compounds of formula III exhibit low mammalian toxicity, relative to benzimidazoles. In addition, compounds of formula

III can be dispersed as an aerosol mixture containing one or more active ingredients according to the invention. This mixture is prepared according to conventional methods, wherein the active substance is dispersed in a solvent and the resulting dispersion is mixed with the propellant in a liquid state. These variations as to the use of a particular agent and the type of vegetation to be treated determine the solvent requirements for the concentration of the active ingredient therein. Examples of suitable solvents are water, acetone, isopropanol, and 2-ethoxyethanol.

Appropriate results are obtained when the active substances of the formula III or a mixture containing them are mixed with other agriculturally used materials to be applied to the plants, plant parts and their surroundings. These materials include fertilizers, fungicides, insecticides, other herbicides and soil conditioners.

The various compounds of formula III to be used as active herbicidal agents are:

195700 7, evaluated after application before emergence in various plant species. In this evaluation, a soil containing one part of sand and one part of a crushed top soil layer is prepared, perfectly mixed in a cement mixer. 4.5 liters of this soil is placed in a 25 X X 35 cm galvanized metal bowl and the cellar is below the rim. 2.5 cm deep grooves are made in three rows in about two fifths of the dish. Four corn grains, cotton seed and five soybean seeds are planted in these grooves. In the remaining four trenches, the approximate number of each of the following seedlings is sown in the remaining soil: each of the varieties in a single row, namely: 80-100 seeds, 40-50 seeds, 150-50 seeds and 100- 150 seeds.

A further sufficient amount of soil is then added to sufficiently cover the area.

Thus the weed seeds are covered with a layer of about 6 mm and the seeds of the useful plants with a layer of about 3 cm. -.

. In determining the effect of the composition as a herbicidal composition for pre-emergence use, the area is prepared as described above and placed in a turntable and air vented chamber on the day of sowing or the following day. Herbicidal mixture, bud. the spray emulsion or wettable powder is applied to the surface with a modified De Vilbis atomizer attached to an air source. Twelve and a half milliliters of the mixture to be tested is then applied to each area either on the sowing day or the following day. The intensity of the lesion and the observation of the lesion type are performed, eleven to twelve days after treatment. Damage shall be assessed on the following scale:., - no damage,

1. - slight damage, - moderate damage, - considerable damage ,.

- death. ,

Where more than one determination was made at the indicated amount, the average was calculated to assess the injury. Each compound tested. is prepared for spraying by one of the following methods. In one test. the compound is wetted by stirring in a mortar with one part of polyoxyethylene sorbitan monolaurate. Five hundred . parts of water are slowly added to the resulting cream-colored paste to give an aqueous dispersion with a base concentration of 0.2 percent. The dispersion is suitable for spray application. In the second procedure, the compound is dissolved in one part of acetone. The acetone solution is diluted with nineteen parts of water containing. 0.1% polyoxyethylene sorbitan monolaurate. '

Table 1 shows the evaluation results, column 1 shows the name of the test compound, column 2 the amount in kilograms per hectare at which the compound is applied to the test area, and the remaining columns indicate the degree of damage to certain plant seeds or plant seedlings.

At '(D |' CD

§ i · .cd AI § g w> O ř - <44

CO CM

WHAT

Týt

CM

WHAT

CM

199700 td a

Λ «

E-i

Degree of damage during pre-emergence treatment.

O w

CD

and.

r — I. > cd 42. o o • pR x - (pM zt cd ΰ)

him

CM tM oo

CO * oo

Ed o ř o o SL * SL >> with T2 · £ * ci and S® ^φ r *, 2 u ** τ * &> * go

Φ 2 Z? SV -3S.

Λ,> <ί 3 · Ζί Z <Λ

195708

Some compounds of formula III were evaluated after emergence in plants including maize and some weed species. The evaluation is carried out according to the previous test, except that the dough solution is applied 9 to 12 days after preparation and sowing into the soil. The results are given. in the following table II.

18 $ 10Q

Table Η '' ^: ·· ·. .

Degree of damage during emergence treatment.

compound kg / ha maize cervix scarlet feather cloud · ^: 'k bloody - ·

Oq eo

CO · ν V * 00 • V * f rH γΚ ad in 04, a? O? 04 * .a j = 3 * • M i

I in

I rH> II.

ϋ tí. W Φ ‘tí * - <Λ Λ £ 9 25! Χ ad.

ao θ 'sf οό <α $ 1 03 φ

About the three.

1 * 4> ί <w r *

-iá of 3

19S7Q0

12

N ² - (2,2,3,3-trifluoropropionyl) -N-methoxycarbonyl-3'-nitro-5'-trifluoromethyl-o-phenylenediamine is evaluated for use as emergent herbicide. The evaluation is carried out as described above, but with one higher application rate (16 kg / ha) and for various species such as tomatoes, bloody dew and gooseberry. Certain compounds provide complete death of each of the above species. The herbicidal compounds described above can be formulated and used with known herbicides of any kind. The ratio of the individual components of these mixtures to others is not critical, all ratios providing mixtures that are useful for altering growth. However, in general, mixtures where a substantial proportion of each component is present, such as mixtures wherein the ratio of the individual components is in the range from 1:10 to 10: 1, in particular from 1: 5 to 5: 1, are suitable.

. Known herbicides with which the compounds of formula III are preferably mixed include

N, N-di-n-propyl-2,6-dinitro-4- (trifluoromethyl) aniline,

N, N-di-n-propyl-2,6-dinitro-4-methylaniline, N-ethyl-N-butyl-2,6-dinitro-4- (trifluoromethyl) aniline,

N, N-di-n-propyl-2,6-dinitro-4- (methylsulfonyl) aniline,

N, N-di-propyl-2,6-dinitro-4-sulfamoylaniline,

N, N-di-n-propyl-2,6-dinitro-4-isopropylaniline,

N, N-di-n-propyl-2,6-dinitro-4-tert-butylaniline,

Ν, Ν-bis (2-chloroethyl) -2,6-dinitro-4-methylaniline.

The same results were obtained when another new compound of the formula was combined

III with another dinitroaniline listed above. In general, good results are obtained when the compositions are used in an amount of from 0.55 to

8.8 kg of N- (2,2-difluoroalkanoyl) -o-phenylenediamine per hectare and from 0.28 to 2.77 kg dinitroaniline per hectare.

Almost the same results with those of the previous tests are obtained when NMrifluoroacetyl-N ² - (2-fluoroyl) -5'-methylsulfonyl) -p-phenylenediamine is used.

For comparison, tests were carried out on a compound of the formula.

of known from US Pat. No. 3,557,211, referred to herein as Compound A, while the compound of formula NH -? - cf ₃ <% HCC ixí- _N £

Referred to herein as Compound D, represents the active compound of the invention.

Pre-emergence herbicide test

The assay was performed similarly to the assay described in Table I.

Table Ia

A D

1.1 kg / ha 2.2 kg / ha 4.4 kg / ha 1.1 kg / ha 2.2 kg / ha 4.4 kg / ha maize cotton soya alfalfa sugar beet rice cucumbers dew bloody mustard goosef grass durman

1 '

1 ’

1 '

1 '

T li

5.

2.

2

3 2 3

5 2 5

2

4 3 3

5

5

14

Claims (1)

A herbicidal composition, characterized in that it contains a compound of formula III as active ingredient, OF THE INVENTION where R ² is trifluoroacetyl or 2-furoyl; and R ⁶ is methylsulfonyl and is located from 4 or 5.