CS216829B2 - Herbicide means - Google Patents

Description

The invention relates to a herbicidal composition.

It is known that a number of commercially available herbicides can also seriously damage plants to be protected. This phytotoxic effect is a function of the substance used and is highly weather dependent. Some known herbicides are already very phytotoxic at doses which can be used to control weeds. Recently, many attempts have been made to solve this problem.

According to Hungarian patent No. 165 736, Ν, Ν-disubstituted dichloroacetamides are added to the known herbicides in an amount of 0.0001 to 30% by weight. According to the patent, these compounds are particularly advantageous for use with thiolcarbamate, urea and triazine herbicides.

U.S. Pat. No. 3,131,509 discloses the use of 1,8-naphthalenic acid and derivatives thereof, for example anhydrides, esters, amides, and the like, to reduce the phytotoxicity of known herbicides.

Recently, ongoing research has been conducted to identify other compounds capable of reducing the phytotoxic effect of known herbicides to as low a level as possible.

It has been found that plants can be protected against damage by active herbicides and / or the plant resistance to these compounds can be substantially increased by using a new type of compound.

Accordingly, the present invention provides a herbicidal composition comprising an active herbicidal compound, such as thiolcarbamate, substituted urea, substituted triazine or chloroacetanilide, or mixtures thereof, and additionally an antidote against the compounds of formula I

where

X ¹ is independently oxygen, nitrogen or sulfur; n is independently an integer either 0 if X ¹ on the same carbon atom is a nitrogen atom, where the bond moves to X ¹ , or 1 if X ¹ is an atom oxygen or sulfur,

X ² and X ³ , the same or different, represent a hydroxyl group, a C 1 -C 5 alkoxy group, a C 2 -C 5 alkenyloxy group, an amino group, a C 1 -C 4 alkylamino group, or

2,2, -dimethyl-1,3-oxazolidinyl, n 2 is an integer of 0 or -1 and

Z is C 1 -C 4 alkylene, C 2 -C 4 alkanylene, phenylene, tetrahydrophenylene, hexahydrophenylene or endomethylenetetrahydrophenylene, in an amount of 1 to 50% by weight, based on the weight of the active herbicidal component together with the solid and and / or a liquid carrier and optionally a surfactant, wherein the total amount of the antidote and the active herbicidal component is 10 to 90% by weight of the total weight of the composition.

The term C 1 -C 5 alkoxy preferably means C 1 -C 4 alkoxy, preferably methoxy, ethoxy or butoxy. The term C 2 -C 5 alkenyloxy preferably refers to allyloxy.

Using the composition of the invention, weeds can be controlled by applying an effective amount of the composition of the invention to the plants.

At the same time, it is possible in this way to protect crops from damage that could otherwise be caused by the herbicidal compound, in particular by incorporating the plant protection compound against the herbicide effect into the soil before or simultaneously with the herbicidal compound.

The term antidote refers to a compound that prevents damage to plants that might otherwise be caused by the herbicidal compound.

The antidote according to the invention is usually used in an amount of 1 to 50% by weight, based on the amount of the herbicidal compound.

Table I lists some of the compounds that are typical antidotes of the invention together with their physical constants.

Number ni ZX ¹ , to X ² X ³ Compound Physical constants Boiling point, melting cn o

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Number ni ZX ¹ 112 X ² X ³ Compound 'Physical constants Boiling point, melting point ___ (° C)

Phenylene O1 2,2-Dimethyl-2,2-dimethyl-bis- (2,2-dimethyl-1,3-melting point 35)

-1,3-oxazolium-1,3,3-oxazolium-oxazolidine acid (decomposition)

O r — I p

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The antidotes of formula I are effective in admixture with thiolcarbamates, substituted ureas, substituted triazines, and chloroacetanides having herbicidal activity.

Most of the compounds of the present invention are prepared by known methods.

Endomethylenetetrahydrophthalic acid, i.e. compound No. 16, can be obtained by reacting malelic acid with cyclopentadiene in a yield of 94%, as described, for example, in Czechoslovak Patent Specification 86 914.

Terephthalic acid, Compound No. 11, can be obtained, for example, according to the method of Organic Syntheses Cell. St. III, 791 oxidation of p-methylacetophenenone in a yield of 84-88%.

The method of U.S. Patent No. 2,856,424 provides isophthalic acid, Compound No. 10, for example, by oxidation of m-xylene.

The dicarboxylic acid esters, i.e., compounds Nos. 3, 5, 6, 8, 9, 12, 13, 14 and 15, can be obtained by reacting the corresponding dicarboxylic acid anhydride with the corresponding alcohol, for example, according to British patent no. 645 21.8.

The dicarboxylic acid amides, compounds Nos. 1, 4, 7, 17 and 18 can be obtained by the process of U.S. Pat. No. 2,820,021 by reacting a dicarboxylic acid dichloride with the corresponding amine. The thioacid amides, compounds 25 and 26 can be obtained in an analogous manner, starting from the corresponding thiocarboxylic acids.

The preparation of the novel compounds Nos. 19, 20, 21 and 22 is shown in the following examples.

Example 1

A process for the preparation of bis-N, N- (2,2-dimethyl-1,3, -oxazolidine) phthalic acid

To a 250 ml flask equipped with a stirrer, thermometer and funnel is added a solution of 10.1 g (0.1 mod) of 2,2-dimethyl-1,3-oxazolidine in 80 ml of benzene and then dropwise a drop of 4.4. g (0.11 mod) of sodium hydroxide in 15 ml of water at 0 ° C with stirring. Then, a solution of 10.2 g (0.05 mol) dd was added to the mixture ^. of phthalic acid chloride in 20 ml benzene, the temperature must not exceed 6 ° C. The reaction mixture was stirred at room temperature for 2 hours and allowed to stand overnight. The two phases are separated, the benzene phase is dried and distilled under vacuum. The remaining thick oily liquid was digested with petroleum ether and the crystalline product obtained was recrystallized from cyclohexane. The melting point of the final product is between 13 ° C and 132 ° C.

Analysis:

Calculated:

% C, 65.04;% H, 7.28;

found:

65.02% C, 7.14% H, 8.7: 3% N.

The spectrum in infrared light also corresponds to the structure of the resulting product. Example 2

Method of making bis-N, N- (2,2-dimethyl-1,3-oxazolidinic acid terephthalic acid) In a 500 ml flask equipped with a stirrer, a thermometer and a funnel is added a solution of 10.1 g (0.1 mol). 2,2-dimethyl-1,3-oxazolidine in 80 ml of benzene and then a solution of 4.4 g (0.11 mol) of sodium hydroxide in 15 ml of water at 0 ° C is added dropwise with stirring. solution of 10.2 g (0.05 mol) of terephthalic acid dichloride in 140 ml benzene portionwise so that the temperature did not exceed 6 ^Q C. the reaction mixture is then stirred for 2 hours, whereupon the product precipitated by addition of hexane. the resulting precipitate was collected by filtration 197 DEG-201 ^DEG C. The melting point of the title product, purified by recrystallization from absolute ethanol, is 207 DEG C .;

Analysis:

Calculated:

% C, 65.04;% H, 7.28;

found-:

% C, 64.91;% H, 7.30;

The spectrum in infrared light also corresponds to the predicted structure of the final product.

Example 3

Process for the preparation of terephthaloyl-N- (2,2-dimethyl-1,3-oxazolidine)

To a solution of 5.0 g (0.05 mol) of 2,2-dimethyl-1,3-oxazoate in 40 ml of benzene, 4.4 g (0.11 mol) of sodium hydroxide and 15 ml of water were added as described in the previous examples. 10.2 g (0.05 mol) of terephthalic acid dichloride are added to the reaction mixture. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 3, benzene was distilled off, the residue was dissolved in acetone and precipitated with petroleum ether. The crystalline product is collected by filtration, washed with water and dried. Its melting point is 318-320 ° C.

Analysis:

Calculated:

% C, 62.64;% H, 6.07;% N, 5.62;

found-:

% H, 6.00;% N, 5.85.

The spectrum in infrared light also corresponds to the predicted structure of the final product.

The compositions and compounds of the invention may be used in any conventional form. For example, it is possible to formulate the herbicidal compounds α and anti-antidote into an emulsifiable concentrate, wettable powder, granulate, powder or other form. The compositions of the invention may be incorporated into the soil before or after sowing. However, it is also possible to use the herbicidal compounds and natidote separately and to incorporate them into the soil one after the other. In a preferred embodiment of the invention, the seeds are pickled with a suitable antidote of formula I before sowing and the herbicidal compounds are incorporated into the soil before or after sowing. . The compounds of formula (I) may be formulated in the same manner as active herbicides. By thiolcarbamates, substituted ureas, triazines, chloroacetanilides, as such or in the form of various mixtures.

The following Examples 4 to 6 illustrate a process for preparing compositions containing compounds of Formula I.

Example 4

A powder containing isophthalic acid (Compound No. 10) g of isophthalic acid, 17 g of kaolin, 8 g of amorphous silicic acid (Ultrasil), 2.5 g of aliphatic alcohol sulfonate and 2.5 g of powdered sulfite · lye is mixed and finely ground. The wettability of the powder is 97%. Example 1 a d 5

The emulsifiable concentrate containing dimethyl maleate (Compound No. 8) g of dimethyl maleate and 5 g of emulsifying agent (Emulsogen I 40) is diluted to a volume of 100 ml with isopherone and diluted to the desired concentration with water before use.

Example 6

The emulsifiable concentrate containing phthalic acid dimethyl ester (Compound No. 12) g of phthalic acid dimethyl ester and 5 g of emulsifying agent (Emulsogen I 40) was diluted to 100 ml with xylene. Prior to use, the concentrate is diluted to the desired concentration with water and the emulsion applied to the soil as a spray.

The compounds of the invention in the form of antidic herbicidal compositions were tested as described in Examples 7-13.

Alafone = N- (3,4-chlorophenyl) -N‘-methoxy-N‘-methylurea

Eptam = S-ethyl-N, N-dipropylthiolcarbate,

Sencor = 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5-one,

Lasso = 2-chloro-2 ', 6'-diethyl-N- (methoxymethyl) -acetanilide.

Example 1 a d 7

The adverse effect of Afalon on sunflowers was investigated. At the same time, the extent to which sunflower resistance against said herbicidal agent has been investigated has been investigated using the known antidote N, N-diallyl-2,2-dichloroacetamide and various compounds of formula I.

The experiments were carried out on 10 m ² fields and were repeated four times. Afalone 50 was used ^! WP at a rate of 5 kg / ha. The antidote was applied simultaneously with Afalon in aqueous suspension as a spray.

The weeds were only mechanically controlled on the control fields. The sunflower green matter from the treated fields was expressed as a% of the sunflower green matter from the control fields taken as 100%. The results are shown in Table 2 below.

Table 2 ·

Treatment

Rate (kg / ha)

0,5 1,0 2,0 Green matter (%)

Afalone 41 41 41 Afalone + N, N-diallyl-2,2-diohloroacetamide 48 51 57 Afalone + Compound No. 11 52 67 80 Afalone + Compound No. 15 52 78 87 Afalone -j- compound No. 18 67 78 , 95 Afalone + Compound No. 21 Θ8 76 / 98 Inspection (mechanical 100 ALIGN! 100 ALIGN! 100 ALIGN!

no weeds)

ΙΟ

The data presented in Table 2 clearly show that the formulation containing the antidote of the invention, concurrently with the herbicidal compound Afalon, has a substantially lower phytotoxic effect than Afalon as such as Aion in N, N-diallyl-2,2-dichloroacetamide . By using the compositions according to the invention, in particular those containing compounds Nos. 18 and 21, a green mass is obtained, the mass of which is almost identical to that of sunflowers obtained from the control fields on which the weeds were only killed mechanically.

EXAMPLE 8 The procedure described in the Example was repeated except that the sunflower seeds were stained with a composition containing an antidote before sowing and the Afalon 50 WP herbicide was applied to the soil after sowing at a rate of 5 kg / ha as a spray.

In this case, the lesser damage was even more pronounced than in the method of Example 7. The results shown in Table 3 show that the sunflower green matter obtained from the treated fields was virtually identical to the green sunflower matter obtained from the weed control fields only mechanically.

Table 3

Treatment 0.5 Dose (kg / qj 1.0 green matter (% j Afalone 41 41 Afalone + N, N-diallyl-2,2-dichloro- 62 71 acetamld Afalone + Compound No. 11 78 95 Afalone. + Compound No. 15 68 82 Afalone + Compound No. 18 7.0 98 Afalone + Compound No. 21 79 99 Inspection (mechanical removal) 100 ALIGN! 100 ALIGN!

weeds)

Example 9

The toxic effect of Eptam was investigated; 6 E on corn. At the same time, it was investigated how to improve the resistance of maize to this herbicide using the known antidotes of 1,8-naphthalenic anhydride and N, N-diallyl-2,2-dichloroacetamide together with various antidotes of the formula I at a dose of 0.5, 1, 0 and 2.0 kg / ha. A herbicidal and antidote formulation was introduced into the soil prior to sowing. All experiments were repeated four times.

Table I below shows the green mass of maize from treated fields, expressed as% of the green mass of maize from control fields, which was taken as 100% and on which the weeds were only killed mechanically.

Table 4

Treatment 0.5 Rate (kg / ha) 1.0 · green matter (% j 2,0 Eptam 48 48 , 48 Eptam + 1,8-naphthalene acid- 60 64 70 seline in anhydride form Eptam + N, N-diallyl-2,2-di- 69 84 92 chloracetamide Eptam -j- Compound No. 16 70 85 93 Eptam -j- Compound No. 19 76 88 94 Eptam + Compound No. 21 77 87 95 Eptam + Compound No. 23 69 85 , 94 Inspection (mechanical 100 ALIGN! 100 ALIGN! 100 ALIGN!

weeding)

It can be seen from the above figures that the protection afforded by the antidotes of the invention is substantially better than that of 1,8-naphthalenic anhydride and slightly better than that of N, N-diallyl-2,2-dichloroacetamide.

ce against this herbicide with an anhydride, 1,8-naphthalic acid, N, _N-diallyl-2) 2-dichloiracetamidu and various antidotes of the formula I. in each case 100 kg of maize seed was stained with 0.25, 0.50 and 1, 00 kg of the above substances and

Example 10 ' this corn was sown into fields, treat- 13 liters / ha Eptam 6 E. All The adverse effect of the pieces were performed four times. Eptane on corn. At the same time, it was investigated how to increase the resistance of corn- The results are shown in Table 5. Table 5 Treatment Dose (kg / qj 0.25 0.50 1.00 green matter (%) Eptam , 48 48 46 1,8-naphthalic acid anhydride 68 70 78 N + N-N-N-diallyl-2,2-dichloroacetate • 65 75 80 amide-.beta.-Eptane Compound No. 16 + Eptam 65 78 82 Compound No. 19 + Eptam 68 80 95 Compound No. 21 + Eptam .70 82 98 Inspection (mechanical 100 ALIGN! 100 ALIGN! 100 ALIGN! weed control) / It is clear from the data in Table 5 that: du and at the same time some antidotes according to pickling of corn seeds examined invention. compounds of the formula I provides sling- Experiments were carried out on experimental experiments. Complete protection against damage caused by Eptam. evoke- 10 m ² , each experiment was repeated four times. Herbicidal composition Sencor was used in a dose 1.5 kg / Ha, anti-

Example 11 The toxic effect of the Sencor herbicidal composition on soybeans was investigated. At the same time, the extent to which soybean resistance against the above herbicide by using known antidotes, N, 8-naphthalenic anhydride and N, N-diallyl-2,2-dichloroacetamidine, was used at doses of 1.0 and 2.0 kg / ha. Both the herbicide and the antidote were used in aqueous suspension.

Evaluation of the experiments was carried out in the same manner as in the previous examples. Weed control was performed only by mechanical means.

The results obtained are shown in Table 6 below.

Table Θ

Treatment 1.0 Dose (kg / ha) green matter (%) 2,0 Sencor 17 17 Sencor + 1,8-naphthyric anhydride 41 52 indoor Sencor -) - N, N-diallyl-2,2-dichloroacetate 21 '26 amid Sencor + Compound No. 10 51 66 Sencor + Compound No. 11 56 68 Sencor Compound No. 19 58 61 Inspection (mechanical skin removal) 100 ALIGN! 100 ALIGN!

vele j

In conclusion, the antidotes of the invention provide sufficient protection for soybeans against damage by Sencor, far superior to the known antidotes.

Example 12 • The toxic effect of Sencor on soybeans was investigated and at the same time the extent to which it was possible to protect against this toxic effect by using 1,8-naphthalenic anhydride and N, N-diallyl-2,2-dichloroacetamide as well as some compounds of formula I.

Soybean seeds were pickled at 0.25 and 0.50 kg / 100 · kg seeds, and the Sencor herbicide was applied to the soil after sowing at 1.5 kg / ha as a spray.

The evaluation was performed as in the previous examples. The results are shown in Table 7.

Table 7

Treatment Dose (kg / q)

0,25 0,5 green matter (%)

Sencor 1,8-Naphthalic Acid anhydride-J-Sencor

N, N-diallyl-2,2-dichloroacetamide-44-Sencor Compound No. 10 + Sencor Compound No. 11 - | - Sencor Compound No. 19 -j-Sencor

Control (mechanical removal of ^weeds]! From the obtained results it can be concluded that the antidotes of the invention provide better protection in the event that they are used for seed dressing after dusting than in the form of aqueous suspension in the case of compound no. 19 but for example, be achieve virtually complete protection of the crop against damage by the herbicide.

Example 1 a d 13

17 17 26 28 70 82 69 87 68 78 72 95 100 ALIGN! 100 ALIGN!

so on sorghum. At the same time, it has been investigated to what extent the crop can be tolerated against said herbicide using the known antidote N, N-diallyl-2,2-dichloroacetamide and some antidotes according to the invention.

^! The crop seeds were treated with an antidote at a dose of 0.25 and 0.50 kg antidote / kg seed and the Lasso 48 EC herbicide was applied to the soil after sowing at a rate of 45 liters / ha.

The toxic effect of the herbicide LasTable 8 was investigated

Treatment 0.25 Dose (kg / q) green matter (%) 0.50 Lasso 38 , 38 N, N-diallyl-2,2-dichloroacetamide + 90 , 95 + Lasso Compound No. 6 + Lasso 95 100 ALIGN! Compound No. 1,2 Lasso 92 100 ALIGN! Compound No. 25 + Lasso 98 105 Inspection (mechanical removal) 100 ALIGN! 100 ALIGN!

weeds)

The results shown in Table 8 clearly show that the adverse effect of the herbicide can be virtually completely eliminated by seed dressing with an antidote of the invention, moreover, the green crop mass was treated with compound 2; 5 higher than the crop mass from the fields where> mechanic.

Examples 7 to 11 and Tables 2 to 8 clearly show that herbicide resistance can be substantially increased in this way and, in some cases, herbicide damage completely eliminated by compounds of formula I. The tests were carried out on four different crops and herbicidal compositions of four different types, effect is therefore documented in a wide range. It will be understood that numerous other modifications are possible and are within the scope of the invention.

Claims (2)

What is claimed is: 1. A herbicidal composition comprising an active herbicidal compound, namely a thiolcarbamate, a substituted urea, a substituted triazine or a chloroacetanilide, or mixtures thereof, and, in addition, an antidote against said compounds. the general formula U) where X ¹ is independently oxygen, nitrogen or sulfur; n is independently an integer of either 0 if X ¹ on the same carbon atom is a nitrogen atom, where the bond moves to X ¹ , or 1 if X ¹ has the meaning an oxygen or sulfur atom, X ² and X ³ , the same or different, represent a hydroxyl group, a C 1 -C 5 alkoxy group, a C 2 -C 5 alkenyloxy group, an amino group, a C 1 -C 4 alkylamino group, or 2,2, -dimethyl-1,3-oxazolidinyl, nz being an integer of 0 or 1; and Z is C 1 -C 4 alkylene, C 2 -C 4 alkanylene, phenylene, tetrahydrophenylene, hexahydrophenylene or endomethylenetetrahydrophenylene. the remainder of the invention is present in an amount of 1 to -50% by weight based on the weight of the active herbicidal component together with a solid and / or liquid carrier and optionally a surfactant, the total amount of antidote and active herbicidal component being W- up to 90% weight of the composition. 2. A composition according to claim 1 wherein the antidote of formula (I) is any of the following: oxalic acid diamide, oxalic acid monoethyl ester, imalonic acid diethyl ester, succinic diamide, adipic acid dimethyl ester, adipic acid diethyl ester, adipic acid diamide, malemic acid diethyl ester, · maleate diethyl ester, isophthalic acid diethyl ester, terephthalic acid dimethyl ester, terephthalic acid dimethyl ester phthalic acid, dittyl esters of italic acid, diallyl phthalic acid ester, endomethylenetetrahydro-ththalic acid, isophthalic acid amide, terephthaloyl amide, bis- (2,2-dimethyl-1,3-oxazolidine) phthalic acid, bis- (2,2-dimethyl-l, 3-oxazolidin} isophthalic acid 2,2édimethyl-l, 3 ^<i oxazine <riídtntereftalovou, terephthaloyl-2,2, -dimethyl-l, 3-oxazolidine acid dinitrile, phthalic acid dlnitril terephthalic acid, isophthalic acid dithionamide, terephthalic acid dithionamide.