HU221245B1 - Herbicidal composition with improved selectivity with cultivated plants containing 2-chloro-n-(2-ethyl-6-methyl-phenyl)-n-(izopropoxy-methyl)-acetamide and s-ethyl-n,n-di-izobutyl-tiocarbamate - Google Patents

Abstract

The invention uses 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(isopropoxymethyl)acetamide (propisochlor) and S-ethyl-N,N-diisobutylthiocarbamate (butylate) It applies to herbicide preparations containing increased crop selectivity, which are suitable for eradicating monocotyledonous and dicotyledonous weeds of corn, beans, peas, horse beans, soybeans, cotton, sunflowers, and sugar beets. The preparations contain the thiocarbamate active ingredient relative to the chloroacetamide active ingredient in a weight ratio of 1:3–1:1, preferably 1:2–1:1.5. The total amount of active substances in the preparations can range from 5 to 90 parts by weight, accompanied by solid or liquid carriers and surfactants. ŕ

Description

BACKGROUND OF THE INVENTION This invention relates to an enhanced crop comprising 2-chloro-N- (2-ethyl-6-methylphenyl) -N- (isopropoxymethyl) acetamide (propisochlor) and S-ethyl-N, N-diisobutylthiocarbamate (butylate). selective herbicidal compositions suitable for the control of monocotyledonous and dicotyledonous weeds of maize, beans, peas, broad beans, soya, cotton, sunflower and sugar beet.

The herbicidal compositions of the invention are known herbicides. The chloroacetamide component of the combination according to the invention is known from Hungarian Patent No. 208,224 and French Patent No. 2,514,611. The two patents do not appreciate the biological activity of the chloroacetamide in the combination according to the invention. In the French patent, the chloroacetamide component of the combination can be used only in maize and only with antidote. However, recent studies have confirmed the correctness of the compound disclosed in Hungarian Patent Application No. 208,224, which states that it can be used in soybean, potato, sugar beet, cotton and sunflower without antidote in many crop crops.

The thiocarbamate component of the composition of the invention is described in U.S. Patent Nos. 2,913,327 and 3,175,897. Formulations containing thiocarbamates such as EPTC (Niptan Super 800 EC; Nitrochemistry Co.) or butylate (Then +; Zeneca) can be used primarily in beans, peas, soy, sunflower and cotton without the need for an antidote. Supplemented with antidotum, thiocarbamates also have a field of application in maize.

Such antidotes are disclosed in Hungarian Patent Nos. 187,284 (dioxolane type), 181,621 (thiocarbamic acid type) and 176,784 (dichloroacetamide type). Combinations of herbicides containing a chloroacetamide derivative and a thiocarbamate are known in agricultural practice. Such combinations are disclosed in Hungarian Patent Nos. 209,234 and 210,367. It is common to both patents that the compositions of the present invention do not harm the maize unless the combination contains chlorotetamide and thiocarbamate herbicides as an antidote.

Our studies have surprisingly found that when 2-chloro-N- (ethyl-6-methylphenyl) -N-isopropoxymethyl-acetamide (propisochlor) and acetyl-N, N-diisobutylthiocarbamate ( butylate) did not harm the maize even if the combination did not contain an antidote.

However, this surprising effect occurred only when both the chloroacetamide and thiocarbamate component contained a branched alkyl group, in this case isopropyl and isobutyl groups. This increased crop selectivity was abolished when the butylate in the combination was replaced with another thiocarbamate derivative, such as S-ethyl-N, N-di-n-propylthiocarbamate (EPTC), or if the chloroacetamide branched alkyl group was not in the chain. at the end.

The ratio of herbicides to chloroacetamide in the compositions according to the invention may range from 1: 3 to 1: 1, preferably from 1: 2 to 1: 1.5.

The ratio between the components will depend on the chemical and physical properties and spectrum of action of the combination partners and any other conditions known to those skilled in the art.

The combinations according to the invention are particularly preferred for the eradication of monocotyledonous and dicotyledonous weeds of maize, beans, peas, broad beans, soya, cotton, sunflower, sugar beet, preferably in an amount of 1 to 7 kg / ha, preferably 2 to 6 kg / ha.

The compositions of the present invention are prepared in high concentrations and can be diluted to form the directly applicable product.

Formulations according to the invention are also intended to be mixed in a container or spray device and diluted to the desired extent before use.

The compositions of the invention may have a total active ingredient content of from 5 to 90 parts by weight.

The formulations of the present invention may be solid or liquid formulations customary in agricultural practice, the physical and chemical properties of which make it possible to prepare the active ingredients. The formulations contain the active compounds together with an acceptable solid or liquid carrier in agriculture and, if necessary, a surfactant.

The compositions may also contain additives which may favorably affect the action, thereby reducing the volatility of the active substances or facilitating their application.

Examples of such additives are protective colloids, thickeners, adhesives, stabilizers and solid carriers with high adsorption properties.

In addition to the above amounts of active ingredients, the compositions of the present invention will generally contain from 10 to 95 parts by weight of a solid or liquid carrier and optionally a surfactant.

The carrier may be any agriculturally acceptable organic or inorganic material of natural or artificial origin. The surfactant may be an emulsifier, dispersant, or wetting agent, which may be ionic and / or nonionic.

The compositions of the invention may also be used in combination with other plant protection products that are compatible with the composition of the invention.

The compositions of the present invention are applied in the context of a plant protection process, wherein the soil is treated simultaneously or sequentially with the components of the herbicidal composition of the invention.

The amount of each active ingredient used is such that effective weed control is achieved.

Application of the formulations, if appropriate in a properly diluted form, may be accomplished by conventional means and techniques, such as spraying, spraying, spraying, dusting.

The following examples illustrate the invention.

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Preparation of granulate preparation

Example 1 5 G 1 parts by weight 0.25 parts by weight 0.25 parts by weight 3.50 parts by weight 91.0 parts by weight

2-chloro-N- (2-methyl-6-ethylphenyl) -N- (isopropoxymethyl) acetamide

S-ethyl-N, N-diisobutylthiocarbamate epichlorohydrin cetyl polyglycol ether polyethylene glycol kaolin (particle size 0.3-0.8 mm)

The active compounds were mixed with epichlorohydrin and dissolved in 6 times acetone. Polyethylene glycol and cetyl polyglycol ether are added to the solution.

The solution thus obtained was sprayed onto kaolin and then acetone was removed under reduced pressure.

Preparation of emulsifying concentrates

Example 2 750 EC parts by weight S-ethyl-N, N-diisobutylthiocarbamate parts by weight 2-chloro-N- (2-ethyl-6-methylphenyl) -N-isopropoxymethylacetamide 5 parts by weight Tensiofix 7438 (Carochim SA Belgium) part by weight Tensiofix 7453 (Carochim SA Belgium) part by weight xylene

Example 3 750 parts by weight of S-ethyl-N, N-diisobutylthiocarbamate in parts by weight of 2-chloro-n- (2-ethyl-6-methylphenyl) -N-isopropoxymethylacetamide 5 parts by weight of 2- (dichloro) -methyl) -2-phenyl-1,3-dioxolane (as antidote) part by weight Atlox 4902 (ICI Specialty Chem.) part by weight Atlox 4903 (ICI Specialty Chem.) part by weight benzene

Example 4 75 parts by weight of S-ethyl-N-di-n-propylthiocarbamate 75 parts by weight of 2-chloro-N- (2-ethyl-6-methylphenyl) -N-isopropoxymethylacetamide 10 parts by weight of 2- (dichloromethyl) -2-methyl-1,3-dioxolane (as an antidote) part by weight from 930 (from AG Sweden) to part from 935 (from Sweden Sweden) part by weight xylene

Example 5 75 EC 50 parts 25 parts 25 parts 5 parts 15 parts

S-ethyl-N, N-di-n-propylthiocarbamate 2-chloro-N- (2-ethyl-6-methylphenyl) -N (isopropoxymethyl) -acetamide From 930 (From AG to Sweden) From 935 (From AG to Sweden) xylene

Example 6 720 FC by weight of 2-chloro-N- (2-ethyl-6-methylphenyl) -N-isopropoxymethyl-acetamide by weight by weight with Atlox 4902 (ICI Specialty Chem.) 5 parts by weight with Atlox 4903 (ICI Specialty Chem.). ) parts by weight of xylene

Example 7 720 FC parts by weight

7.2 parts by weight 5 parts by weight 10.8 parts by weight

2-chloro-N- (2-ethyl-6-methylphenyl) -N- (isopropoxymethyl) acetamide

2- (dichloromethyl) -2-phenyl-1,3-dioxolane (as antidote)

Atlox 4902 (I.C.I. Specialty Chem.) Atlox 4903 (I.C.I. Specialty Chem.) Xylene

Example 8 720 EC parts by weight of S-ethyl-N, N-di-n-propylthiocarbamate 7.2 parts by weight of 2- (dichloromethyl) -2-methyl-1,3-dioxolane (as an antidote) AG Sweden) parts by weight from 935 (from AG Sweden)

10.8 parts by weight of xylene

Example 9 720 EC parts by weight S-ethyl-N, N-di-n-propylthiocarbamate parts by weight Bovine 930 (By A.G. Sweden) parts by weight Bolt 935 (by A.G. Sweden) parts by weight xylene

Example 10 720 EC parts by weight S-ethyl-N, N-diisobutylthiocarbamate 7.2 parts by weight 2- (dichloromethyl) -2-phenyl-1,3-dioxolane (as an antidote) part by weight Tensiofix 7438 (Carochim SA Belgium) Tensiofix 7453 (Carochim SA Belgium)

10.8 parts by weight of xylene

Example 11 720 EC parts by weight of S-ethyl-N, N-diisobutylthiocarbamate parts by weight Tensiofix 7438 (Carochim S.A. Belgium) parts by weight Tensiofix 7453 (Carochim S.A. Belgium) parts by weight xylene

Example 12 750 EC parts by weight of S-ethyl-N, N-diisobutylthiocarbamate in 2 parts of 2-chloro-N- (2-ethyl-6-methylphenyl) -N- (1-methyl-2-methoxyethyl) acetamide parts by weight Tensiofix 7438 (Charochim SA Belgium) parts by weight Tensiofix 7453 (Charochim SA Belgium) parts by weight xylene

Biological examples

We further investigated the effects of the compositions of the present invention or its components on maize and grass.

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Example 13 We made thiocarbamate derivative herbicides. The perme30 χ 40 χ 19 cm culture pots After 10 cm of netting, an additional 2 cm sand layer was applied to the supernatant filled with quartz sand and then to the culture color. The treatments were watered daily and 100-100 grains of corn seed (hybrid: lesions every 5 days and finally after 4 weeks) were seeded into phytotoxic vessels. After sowing, we sprayed it on the sand. (Table 1).

Table 1

Treatment Application rate 1 ha Hatched plant pcs Distorted plant% Death% Height cm control 0 97 0 0 40 Example 8 Formulation 10 96 1 0 36 Example 9 Formulation 10 90 83 91 31 Example 10 Formulation 10 97 0 0 39 Example 11 Formulation 10 90 80 90 34

Table 1 shows that thiocarbamate-derived herbicides without antidote are not suitable for maize weed control.

Example 14 14. 40 χ 19 cm culture pots were filled 12 cm deep with quartz sand and brown forest soil 25

With a 1: 1 weight ratio of 100-100 grains of corn seed. The chloroacetamide derivative herbicide was sprayed onto the soil surface. The culture vessels were watered daily and the phytotoxic lesions evaluated every 5 days and finally after 4 weeks (Table 2).

Table 2

Treatment Application rate 1 ha Hatched plant pcs Distorted plant% Death% Height cm Example 6 Formulation 5 97 0 0 38 Example 7 Formulation 5 96 0 0 37 control 0 97 0 0 40

As shown in Table 2, the chloroacetamide component of the present invention did not affect the development of maize either with or without an antidote.

EXAMPLE 75 Breeding pots of χ40 χ 19 cm were filled to a depth of 10 cm with a 1: 1 weight ratio of quartz sand and brown forest soil with 100 to 100 pieces of corn kernels (hybrid: DeKalb 524). Thiocarbamate-chloroacetamide herbicide combinations were sprayed onto the soil. After spraying, another 2 cm crayon40 was applied to the surface. Treatments were watered daily and phytotoxic lesions were evaluated every 5 days and finally after 4 weeks (Table 3).

Table 3

Treatment Application rate 1 ha Hatched plant pcs Distorted plant% Death% Height cm control 0 97 0 0 40 Example 2 Formulation 10 97 1 0 37 Example 3 Formulation 10 96 1 0 37 Example 4 Formulation 10 94 1 1 38 Example 5 Formulation 10 82 79 82 31

Table 3 shows that combinations of chloroacetamide and thiocarbamate containing branched alkyl groups do not require the use of an antidote. S-ethyl-N, N-diisobutyl-thiocarbamate of the invention; and 2-chloro-N- (2-ethyl-6-methylphenyl) -N- (isopropoxymethyl) -acetamide herbicides (preparation of Example 2) did not harm the maize even if the combination did not contain an antidote . S-ethyl-N, N-di-n-propylthiocarbamate and 2-chloro-N- (2-ethyl

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In order to prevent the corn-damaging effect of the combination of 6-methylphenyl) -N- (isopropoxymethyl) -acetamide, herbicides also had to be sprayed with an antidote.

Example 16 5

In the field experiment, the test preparations were applied to small plots (2.1x10 m, in four replicates), 6-8 cm deep before sowing corn. After application, maize was planted in the plot (hybrid: DeKalb 524, population 62,000 / ha). In the study, the herbicidal activity and the extent of maize damage were evaluated on day 42 after sowing. The assessment is based on the following internationally accepted EWRC Score.

Understanding the EWRC Scale

Herbicide% General impression EWRC-scale CRTC Phytotoxic symptoms seen in crop plants 100 excellent 1 There are no 98 very good 2 very mild symptoms 95 good 3 mild symptoms 90 satisfying 4 strong but possibly transient symptoms; 82 in question 5 symptoms with unknown effect 70 unsatisfactory 6 noticeably harmful symptoms 55 bad 7 symptoms of severe injury 30 very bad 8 very severe damage symptoms 0 unusable 9 total destruction

Table 4

treatments Dose 1 / h Herbicide% Phytotoxic effects a maize EWRC ECHCR Panmen ABUTH AMARE Control (hooded) - 100 100 100 100 1 Control (gyomos) - 0 0 0 0 1 Example 2 5 98 100 87 93 1 Example 2 Formulation 10 100 100 91 97 1 Example 3 Formulation 5 97 98 85 90 1 Example 3 Formulation 10 100 100 93 95 1 Example 4 Formulation 5 99 82 67 85 1 Example 4 Formulation 10 100 93 82 91 3 Example 5 Formulation 5 98 84 70 86 7 Example 5 Formulation 10 100 95 81 92 9

ECHCR = rooster grass PANMI = millet ABUTH = mulberry AMARE = pig farm

Field studies have repeatedly demonstrated that the combination of the invention does not harm corn even when no antidote is used in combination with herbicides.

Example 17

The phytotoxic effects of the formulations of Examples 2 and 12 on maize were investigated. In both formulations, the alkoxy side chain of chloroacetamide is branched

Except that in the composition of Example 2, the branched alkyl group is in the terminal position. The preparations are under. Example 3 was used.

Table 5

treatments Application rate 1 ha phytotoxicity corn No EWRC Example 2 4.0 0 Example 2 8.0 3 Example 12 4.0 2 Example 12 8.0 5 Received control - 0

From the data in the table it can be seen that the composition containing chloroacetamide having a branched alkyl group has a more favorable phytotoxic effect and thus less damage to the maize than the chloroacetamide containing branching center.

Claims (1)

Patent Claim Point Herbicidal compositions with increased crop selectivity for controlling monocotyledonous and dicotyledonous plants of maize, beans, peas, broad beans, soybean, cotton, sunflower, sugar beet, characterized in that 2-chloro-N- (2-ethyl-6-methylphenyl) -N- (isopropoxymethyl) acetamide and S-ethyl-N, N-diisobutylthiocarbamate, containing the thiocarbamate active ingredient in a ratio of 1: 3 to 1: 1, preferably 1: 2 to 1: 1.5, by weight relative to the chloroacetamide active ingredient; in compositions, the active ingredients may be present in an amount of from 5 to 90 parts by weight, together with solid or liquid carriers and surfactants.