CS217980B2 - Antidote means - Google Patents

Description

(54) Antidotic agent

The invention relates to an herbicidal composition comprising an antidote and thus a reduced phytotoxic effect on crops. As a herbicidal component, the composition comprises at least one compound from the group of thiocarbamates, substituted ureas, chloroacetanilide, triazine and uracil derivatives together with 1 to 50% by weight of the antidote based on the weight of the herbicide. By using the composition according to the invention, weed control can be carried out while avoiding the phytotoxic effect of the herbicidal composition.

SUMMARY OF THE INVENTION The present invention provides an antidote for the protection of crop plants from damage caused by thiocarbamate, substituted urea, substituted triazine, chloroacetanilide or uracil herbicides, characterized in that it contains a compound of formula I as an active ingredient.

(I) where

X is hydroxy, amino (179780), (C 1 -C 5) alkylamino, (C 1 -C 5) dialkylamino, (C 1 -C 5) hydroxyalkylamino or (C 1 -C 5) alkoxyalkylamino; and

Y represents a hydrogen atom, a halogen atom, a nitro group or an alkyl group having 1 to 5 carbon atoms, in a total amount of 10 to 90% by weight together with 90 to 10% by weight of one or more conventional auxiliary agents.

It is well known in the literature that most herbicides damage the crops to be protected. This view can be verified by practical experience. The extent of phytotoxic side effects depends largely on the dose of herbicide used, but is also influenced by other conditions such as weather, soil type and the like. Some herbicides have a selective effect, but at doses necessary to control some weeds they are less selective and adversely affect crop growth and development.

In order to suppress the adverse side effects of herbicides, it has been recommended to use these compounds in admixture with 1,8-naphthalenedicarboxylic acid or derivatives thereof, such as anhydrides, amides and esters, as described in, for example, U.S. Patent 3,131,509.

According to Hungarian patent No. 165 763, the adverse effects of thiocarbamates can be suppressed by mixing them with 0.0001 to 30% by weight of N, N-disubstituted dichloroacetamide.

Problems arising from the phytotoxicity of herbicides can only be partially eliminated by both types of antidotes, which are widely used. Furthermore, the group of phytotoxic herbicides is large and the individual crop types have different sensitivity to individual herbicides, since the beneficial effects of the known antidotes are limited to some combinations of herbicides and crops.

It would be desirable to suppress the phytotoxic side effects of the herbicidal agents so that a new class of antidotes could be found which would have a beneficial effect on the suppression of phytotoxicity, would be inexpensive and would also meet environmental protection requirements.

It has now been found that the compounds of formula I effectively suppress the phytotoxic side effects of a wide variety of herbicidal compositions.

Due to their properties, the compounds of formula I allow the use of herbicides in higher doses without damaging the crops, which is particularly important in areas that are highly infested with weeds. Furthermore, the use of the compounds of the formula I can also prevent damage which may be caused by inaccurate or uneven dosages of the herbicidal substance.

The compounds of the formula I are applied to the plants or to the areas to be treated in an amount of 1 to 50% by weight, based on the weight of the herbicide used, before or simultaneously with the use of the herbicidal composition.

They can be used for pickling or applied to the soil before or after sowing as such or together with a herbicidal composition. The protective effect of the compounds of the formula I does not depend on the method of application of the herbicide. The herbicide can be used before or after sowing without affecting the effect of the antidote on reducing its phytotoxicity.

Some typical compounds of the group of naphthalenecarboxylic acid derivatives of formula I are shown in Table 1. This table also contains the physical constants of these compounds and the publications by which they can be obtained. Other compounds of formula I not listed in the table can be obtained in the same manner. The preparation of some compounds is described in more detail in the examples.

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The novel compositions of the present invention comprise at least one compound having a herbicidal activity from the group of thiocarbamate, substituted urea, substituted triazine, chloroacetanilide or uracil and from 1 to 50% by weight of the antidote of formula I, wherein the herbicidal composition is

X is hydroxy, amino, C 1 -C 5 alkylamino, C 1 -C 5 dialkylamino in each alkyl moiety, C 1 -C 5 hydroxyalkylamino or C 1 -C 5 alkoxyalkylamino; and

Y represents a hydrogen atom, a halogen atom, a nitro group or an alkyl of 1 to 5 carbon atoms.

The composition contains the active ingredients in a total amount of 10 to 90% by weight together with 90 to 10% by weight of one or more conventional adjuvants.

The herbicidally active compounds used in the compositions of the invention are known per se and described, for example, in "Guide to the Chemicals Gray in Crop Protection", ed. Spencer, Ε. Y., Research Branch of the Department of Agriculture, Canada (1968) and later editions.

The compositions according to the invention may contain as herbicidally active substance one or more herbicides of the same type or a mixture of herbicides of different types.

Of the thiocarbamates useful in the composition of the invention, the following are preferred:

S-ethyl-N, N-dipropylthiocarbamate,

S-ethyl-N, N-diisobutylthiocarbamate,

S-propyl-N, N-dipropylthiocarbamate,

S- (2,2,2-trichlorallyl) -N, N-dipropylthiocarbamate a

The S-ethyl-N-cyclohexylethylthiocarbamate of the latter is most preferred.

The most preferred urea-type herbicides are in particular:

N-phenyl-N ‘, N‘-dimethylurea,

N- (4-chlorophenyl) -N‘, N‘-dimethylurea,

N- (3,4-dichlorophenyl) -N -N, N‘-dimethylurea,

N- (3-chloro-4-methylphenyl) -N‘, N‘-dimethylurea,

N- (4-bromophenyl) -N‘-methoxy-N‘-methylurea,

N- (3,4-dichlorophenyl) -N‘-methoxy-N‘-methylurea a

N- (3-chloro-4-bromophenyl) -N‘-methoxy-N‘-methylurea.

The compositions according to the invention preferably contain, as a triazine type herbicide, one of the following compounds:

2-chloro-4,6-bis- (ethylamino) -1,3,5-triazine, 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine,

2-chloro-4,6-bis- (isopropylamino) -1,3,5-triazine,

2-chloro-4-ethylamino-6- (t-butylamino) -1,3,5-triazine,

2- (2-chloro-4-ethylamino-1,3,5-triazin-6-ylamino) -2-methylpropionitrile, 2-methylmercapto-4,6-bis- (isopropylamino) -1,3,5- triazine,

2-methylmercapto-4-ethylamino-6-isopropylamino-1,3,5-triazine,

2-methylmercapto-4-ethylamino-6- (t-butylamino) -1,3,5-triazine a

4-amino-5- (tert-butyl) -3-methylthio-1,2,4-triazin-5-one.

In particular, the following compounds of the chloroacetanilide type herbicides can be used in the compositions of the invention:

N-isopropyl-2-chloroacetanilide,

2‘, 6‘-diethyl-N-methoxymethyl-2-chloroacetanilide,

2‘-ethyl-6‘-methyl-N-methoxymethyl-2-chloroacetanilide a

-N-chloroacetyl-N-butoxymethylene-2 ', 6'-diethylaniline.

Among the uracil type herbicides, the most preferred compounds for use in the compositions of the invention are:

3- (sec-butyl) -5-bromo-6-methyluracil, 3-cyclohexyl-5,6-trimethyluracil and 3- (tert-butyl) -5-chloro-6-methyluracil.

Among the adjuvants used in the compositions of the present invention are especially those commonly used and described in numerous textbooks. These include, in particular, inert carriers, diluents, wetting agents, antifoams, corrosion inhibitors, anti-caking agents and the like.

The composition of the invention may take any conventional form, for example, a wettable powder, an emulsifiable concentrate, a dust, a granule, and the like.

The compositions according to the invention can be advantageously used for controlling weeds.

The method is to apply a herbicidally effective amount of at least one herbicide from the group of thiocarbamate, substituted urea, substituted triazine, chloroacetanilide or uracil and from 1 to 50% by weight of at least one compound of the formula I to the soil separately or simultaneously before or after sowing. Most preferably, the herbicidal composition and antldotum are premixed into a single composition.

Alternatively, the seeds of the crop are pickled prior to sowing 1 to 50% by weight of the active compound of the formula I, based on the weight of the herbicidal composition, and a herbicidally effective amount of at least one substituted urea-substituted triazine thiocarbamate , chloroacetanilide or uracil before or after sowing. In this case too, it is most preferred to pre-treat the herbicidal compound and the compound of formula I together with excipients to form the resulting composition.

The compounds of formula (I) may be formulated in the same manner as compositions comprising these compounds together with a compound having a herbicidal effect.

The herbicidal composition and the antidote are always used in the above ratio. The herbicide dose can be a commonly used dose, but the antidote allows higher doses to be taken without the risk of crop damage. The dose of the herbicide is determined on the basis of various factors, for example depending on the type of weed, the type of herbicide and the type of compound of the formula I, further on the application method and the soil type, generally between 1 and 15 kg / ha.

The invention will be illustrated by the following examples.

He did

1-Naphthalenecarboxylic acid amide

Gaseous ammonia was fed with stirring and cooling to a solution of 95.3 g (0.5 mol) of 1-naphthalenecarboxylic acid chloride in 2000 ml of diethyl ether for 2 hours. The entire process is carried out at 0-5 ° C. The reaction mixture was allowed to warm to room temperature, the solid was filtered off, washed with water and dried to yield

94.6% yielded 81.0 g of 1-naphthalenecarboxylic acid arpide, m.p. 203-204 ° C.

Analysis:

calculated:

N, 8.18; O, 9.34;

found:

N, 8.22. O, 9.37.

Example 2

2-Naphthalenecarboxylic acid amide

Ammonia gas was added at 0-5 ° C with stirring and cooling to a solution of 95.3 g (0.5 mol) of 2-naphthalenecarboxylic acid chloride in 2000 ml of diethyl ether. The precipitated solid was filtered off, washed with water and dried. 70 g of 2-naphthalenecarboxylic acid amide, m.p. 192-193 ° C, are thus obtained. Analysis:

calculated:

N, 8.18; O, 9.34;

found:

N, 8.83. O, 9.53.

Example 3

1-Naphthalenecarboxylic acid N- (2-hydroxyethyl) amide

13.2 g (0.22 mol) of aminoethanol is added dropwise at 0-5 ° C with stirring and cooling to a solution of 19.0 g (0.1 mol) of 1-naphthalenecarboxylic acid chloride in 450 ml of diethyl ether. The reaction mixture was stirred at room temperature for 3 hours. The precipitate formed is filtered off, washed with plenty of water and dried. Yield: 67.6%

14.5 g of 1-naphthalenecarboxylic acid N- (2-hydroxyethyl) amide, m.p. 104 ° C. Analysis:

calculated:

N, 6.51; O, 14.86; found:

N, 6.70; O, 15.01.

Example 4

2-Naphthalenecarboxylic acid N- (2-hydroxyethyl) amide

13.2 g (0.22 mol) of aminoethanol were added dropwise at 0-5 ° C with stirring and cooling to a solution of 19.0 g (0.1 mol of 2-naphthalenecarboxylic acid chloride in 450 ml of diethyl ether). The precipitate was filtered off, washed with water and dried to give 11.6 g of white crystalline 2-naphthalenecarboxylic acid N- (2-hydroxyethyl) amide in 54% yield, m.p. 134 ° C.

Analysis:

calculated:

N, 6.51; O, 14.86; found:

6.58% N, 14.87 θ / ο O.

Example 5

Powder composition containing 1-naphthalenecarboxylic acid (Compound No. 1) g of 1-naphthalenecarboxylic acid is mixed with 17 g of kaolin, 6 g of amorphous silicic acid (Ultrasil), 2.5 g of aliphatic alcohol sulphate and 2.5 g. g of powdered sulphite liquor and the mixture is finely ground. The wettability of the resulting powder is 95%.

Example 6

Powder composition containing 7-methyl-2-naphthalenecarboxylic acid (Compound No. 9) g of 7-methyl-2-naphthalenecarboxylic acid is mixed with 17 g of kaolin and 8 g of amorphous silica, and 2.5 g of sulfonate are added. aliphatic alcohol and 2.5 g of powdered sulphite liquor and the mixture is ground finely. The wettability of the resulting powder is 90 why.

Example 7

1-Naphthalenecarboxylic acid n-propylamide (Compound No. 5) g of 1-naphthalenecarboxylic acid n-propylamide is mixed with 25 g of silicic acid, 2.5 g of aliphatic alcohol sulfonate and 2.5 g of powdered sulfite lye and the mixture is finely ground.The wettability of the resulting powder is 93%.

Example

A composition for use as a dust containing 1-naphthalenecarboxylic acid (Compound No. 1j and Afionone [N- (3,4-dichlorophenyl) -N'-methoxy-N'-methylurea] ation g is mixed with 15 g of acid 1). -naphthalenecarboxylic acid, 35 g of silicic acid, 2.5 g of aliphatic alcohol sulfonate and 2.5 g of powdered sulfite liquor, and the mixture is finely ground to a wettability of 95%.

The following examples describe the tests that have been carried out to detect the phytotoxic side effects of the composition of the invention and the anti-phytotoxicity effects of the antidotes of formula I.

The following herbicides were used in these tests:

Afalon: herbicide containing N- (3,4-dichlorophenyl) -N‘-methoxy-N‘-methylurea, (Hoechst, West Germany).

Eptam: S-ethyl-N, N-dipropylthiocarhamate-containing herbicide (Stauffer Chemical Co., USA).

Sencor: herbicide containing 4-amino-5- (tert-butyl) -3-methylthio-1,2,4-triazin-5-one (Bayer NSR).

Lasso: herbicide containing 2-chloro-2 ', 6'-diethyl-N-methoxymethylacetanilide (Monsanto Co., USA).

Venzar: herbicide containing 3-cyclohexyl-5,6-trimethylenuracil (DuPont de Nemours Co., USA).

Examples

Tests were performed on sunflower. In the first series, the phytotoxic side effect of Afalon was determined and the inhibitory effects of the compound of formula I on this side effect of Afalon were examined. N, N-diallyl-2,2-dichloroacetamide, which is a known agent for the same use, was also used for comparison.

Investigations were performed on 10 m ² boxes, each test was performed four times. Afalon was used as a wettable powder containing 50% active ingredient at a rate of 5 kg / ha. Antidotes were used at various doses. The aqueous suspension containing the antidote is used for spraying on the soil concurrently with spraying carried out by Afalon.

Control boxes were weeded by mechanical means. After four weeks, the sunflower plants were harvested and weighed, and the green matter from the test plots was compared to the green matter from the control plots.

The results are shown in Table 2.

Table 2

Compound 0.5 kg / ha Green matter% Antidotum per dose 1.0 kg / ha 2.0 kg / ha Afalon 41 41 41 Afalon + N, N-diallyl-2,2-dichloroacetamide 48  51 57 Afalon + Compound No. 1 89 87 85 Afalon + Compound No. 2 93 90 87 Afalon + Compound No. 5 80 70 70 Afalon + Compound No. 10 75 60 62 Inspection (mechanical control) 100 ALIGN! 100 ALIGN! 100 ALIGN!

The results shown in Table 2 demonstrate that the compounds of the invention substantially reduce Afalone's crop toxicity, the result is better than that of a mixture of Afalone with the known antidote N, N-diallyl-2,2-dichloroacetamide. Especially when compounds 1 and 2 are used, the green matter of the sunflowers approaches the green matter of the control fields.

He did

The experiments were carried out as in Example 9, except that the sunflower seeds were stained with an antidote before sowing and the fields were treated after sowing with a dose of 5 kg / ha Afalon. In the form of a wettable powder containing 50% of active ingredient.

The results are shown in Table 3.

Table 3

Compound Green matter%

Antidotum in dose

0.5 kg / 100 kg 1.0 kg / 100 kg

Afalon 41 41 Afalon + N, N-diallyl-2,2-di- chloracetamld 62 71 Afalon + Compound No. 1 98 95 Afalon + Compound No. 2 92 93 Afalon + Compound No. 9 82 91 Afalon + Compound No. 10 70 87 Afalon + Compound No. 11 80 85 Inspection (mechanical control) 100 ALIGN! 100 ALIGN!

The results from Table 3 clearly show that the anti-phytotoxicity effect of the compounds of formula I is even more pronounced when used for seed dressing. The sunflower green matter after 4 weeks from the treated fields was practically the same as the green sunflower matter from the control fields from which the weeds were mechanically removed.

Example 11

The experiments were carried out on 10 m ² boxes, each experiment was repeated four times, the test plant being "Beke 270" maize.

Prior to sowing, the test fields were spray-treated with a mixture containing a total of 13 liters / ha of the Eptam 6 E herbicide as a liquid and 0.5, 1.0 and 2.0 kg / ha of the compound of formula I.

The plants were harvested after 4 weeks and weighed. The results were evaluated by comparing the green matter from the test plots with the green matter from the control plots that were mechanically cleared of weeds.

The results are shown in Table 4.

Compound Table 4 73 '...'. □ K® 2.0 kg / ha 0.5 kg / ha Green matter% Antidotum per dose 1.0 kg / ha Eptam Eptam + 1,8-naphthalic anhydride 48 48 48 lendicarboxylové Eptam + N, N-diallyl-2,2-dichloroacetate 60 64 70 amid 69 84 92 Eptam + Compound No. 1 80 87 95 Eptam + Compound 2 78 85 88 Eptam + Compound 3 80 82 82 Eptam + Compound No. 4 87 85 87 Eptam + Compound No. 7 87 89 91 Eptam + Compound No. 8 91 95 95 Inspection (mechanical control) 100 ALIGN! 100 ALIGN! 100 ALIGN!

The results from Table 4 show that the compounds of formula I are far more potent than the known antidotes 1,8-naphthalenedicarboxylic anhydride and N, N-dlallyl-2,2-dichloroacetamide.

Example 12

Suppression of the toxic effects of Eptam was also investigated by seed dressing. 0.25 kg, 0.50 kg and 1.00 kg of the antidote were used for pickling

100 kg of corn seeds. The seeds were sown in fields pre-treated with 13 liters / ha Eptam 6 E.

The test fields were 10 m ² , each experiment was performed four times and evaluated as in the previous examples by comparing the green matter of the plants at 4 weeks of age.

The results are shown in Table 5.

Table 5

Compound

Green matter%

Antidotum in dose

0.25 kg / 100 kg 0.50 kg / 100 kg 1.00 kg / 100 kg

Eptam

Eptam + 1,8-naphthalenedicarboxylic anhydride

Eptam + N, N-diallyl-2,2-dichloroacetamide

Eptam + Compound No. 1

Eptam + Compound 2

Eptam + Compound 3

Eptam + Compound No. 4

Inspection (mechanical control)

48 48 48 68 70 78 65 75 80 90 92 90 85 87. 80 78 80 80 70 70 70 100 ALIGN! 100 ALIGN! 100 ALIGN!

The data from Table 5 shows that the toxic effect of Eptam can be reduced to zero by seed dressing with compounds of Formula I.

Example 13

Experiments were carried out on soybeans using Sencor herbicide. The effect of the compounds of formula I on the suppression of the phytotoxic side effect of the herbicide was investigated in comparison with the known antidotes, 1,8-naphthalenedicarboxylic anhydride and N, N-diallyl-2,2-dichloroacetamide.

The boxes were 10 m ^{2 in} size, each test was performed four times. A dose was used

1.5 kg / ha of Sencor and 1.0 kg / ha or 2.0 kg / ha of antidote before sowing. The results were evaluated as in the previous examples by comparing green matter.

The results are shown in Table 6.

Table 6

Compound

Green matter%

Antidotum in dose

1.0 kg / ha 2.0 kg / ha

Sencor

Sencor + acid anhydride

1,8-naphthalenedicarboxylic acid

Sencor + N, N-diallyl-2,2-dichloroacetamide

Sencor + Compound No. 1

Sencor + Compound No. 2

Sencor + Compound No. 6

Sencor + Compound No. 13

Sencor + Compound No. 14

Inspection (mechanical control)

The data from Table 6 shows that the composition of the invention has far less toxic effect on soybeans than Sencor alone or in admixture with known antidotes.

Example 14

In this experiment, the effect of the compounds of formula I was compared with that of 1,8-naphthalenedicarboxylic anhydride and N, N17

41 52 21 26 70 75 68 70 49 56 55 60 58 65 100 ALIGN! 100 ALIGN!

-dlallyl-2,2-dichloroacetamide in seed dressing. For pickling, 0.25 kg and 0.50 kg of antidote per 100 kg of soy gods were used. The seeds were used to sow the fields and the fields were then treated with 1.5 kg / ha of Sencor.

The results were evaluated as in the previous examples by comparing the green matter of the plants, 4 weeks old.

The results are shown in Table 7.

Table 7

Compound

Green matter% Antidotum per dose

0.25 kg / 100 kg

0.5 kg / 100 kg

Sencor 17 17 Sencor + acid anhydride 1,8-naphthalenedicarboxylic acid 26 28 Sencor + N, N-diallyl-2,2-di- chloracetamide 70 82 Sencor + Compound No. 9 60 65 Sencor + Compound No. 10 48 62 Sencor + Compound No. 16 70 85 Sencor + Compound No. 18 72 90 Inspection (mechanical control) 100 ALIGN! 100 ALIGN! The data shown in Table 7 clearly show of the known antidote N, N-diallyl-2,2-dichloro- suggest that the harmful side effects of the herbicide acetamide. Sencor is much better suppressed in 0.25 kg and 0.50 kg antidotes were used to that antidotes are used to pickle pickling 100 kg seeds. The test fields were men. When using antidotes no. 16 and 18 after sowing was treated with herbicide Venzar po- no harmful side effects of the herbicide Sen- using a composition containing 80% effective cor reduce virtually to zero. substances. The experiments were carried out on boxes at Example 15 size 10 m ² . Each experiment was performed four times. The results were evaluated The experiments were carried out on carrot seeds. As in the previous examples, ve, wherein the compounds of formula I the green matter of plants, four weeks old. have been used to pickle these seeds to ny. it was possible to suppress phytotoxic side effects The results are shown in Table 8. dumbbells herbicide Venzar. In comparative experiments were used for the same purpose Table 8 Compound Green matter% Antidotum in dose 0.25 kg / 100 kg 0.50 kg / 100 kg Venzar 38 38 Venzar + N, N-diallyl-2,2-di- chloracetamide 50 60 Venzar + Compound No. 1 85 90 Venzar + Compound No. 2 80 85 Venzar + Compound No. 5 75 87 Inspection (mechanical control) 100 ALIGN! 100 ALIGN!

The data from Table 8 clearly shows that the harmful side effects can be reduced to virtually zero when the compounds of Formula I are used for seed dressing.

The test results of Examples 9-15, which are summarized in Tables 2 to 8, clearly demonstrate that the compounds of Formula I are capable of suppressing the harmful side effects of known herbicides, in some cases to zero.

Claims (1)

SUBJECT An antidotic agent for the protection of crop plants from damage by thiacarbamates, substituted ureas, substituted triazines, chloroacetanilides or uracils herbicides, characterized in that: as active ingredient of the general formula I contains o- compound if y - + i T ^c · -X (1) OF THE INVENTION where X is hydroxy, amino, C 1 -C 5 alkylamino, C 1 -C 5 dialkylamino in each alkyl moiety, C 1 -C 5 hydroxyalkylamino or C 1 -C 5 alkoxyalkylamino; and Y represents a hydrogen atom, a halogen atom, a nitro group or an alkyl group having 1 to 5 carbon atoms, in a total amount of 10 to 90% by weight together with 90 to 10% by weight of one or more conventional auxiliary agents.