DD242340A1 - HERBICIDE MEDIUM - Google Patents

Abstract

The invention relates to novel selective herbicide combinations, preferably for weed control in crop plants such as in corn, maize and sugar beet pre-emergence and postemergence. As active ingredients they contain combinations of 2-substituted 4-oxo-1,2,3,4-tetrahydro-1,3,5-triazino (1,2-a) benzimidazoles and / or their tautomeric forms in a mixture with 2-chloro 4-ethylamino-6-isopropylamino-1,3,5-triazine, 1,3-dimethyl-1- (benzthiazol-yl-2) -urea, 2,4-dichlorophenoxyacetic acid, 1-butylamino-1-dibutoxyphosphonylcyclohexane , 3-Cyclohexyl-5,6-trimethyleneuracil, 3-methoxycarbonylaminophenyl- (3-methylphenyl) carbamate or 2-methylmercapto-4,6-bis (isopropylamino) -1,3,5-triazine and 2-chloro -4,6-bis (ethylamino) -1,3,5-triazine.

Description

Field of application of the invention

The invention relates to novel, herbicidally active agents for selective weed control in crop stands, especially in cereals, maize and sugar beet.

Characteristic of the known technical solutions

It is known that 2,4-dioxo-1,2,3,4-tetrahydro-1,3,5-triazino (1,2-a) benzimidazoles and / or their tautomeric forms are active agents for biocidal agents, for example Acaricides, insecticides and fungicides are suitable (DE-OS 2144505).

In another patent (DE-OS 2527677) _t relates to a novel process for the preparation of 2,4-dioxo-1,2,3,4-tetrahydro-1,3,5-triazino (1,2-a) benzimidazoles, these compounds are also claimed as fungicidally active agents.

DD-PS 214054 shows that 2-substituted 4-oxo-i, 2,3,4-tetrahydro-1,3,5-triazino (1,2-a) benzimidazoles of the general formula Α _Ί and / or their tautomeric forms), for example of the formula A ₂

be claimed as selective herbicides for use in cereal crops. These compounds are useful in combating hard-to-control weeds and weeds, predominantly in crops of wheat and barley. A disadvantage in the use of these active compounds as herbicides is that relatively high application rates between 4 and 10 kg ai / ha are needed to sufficiently destroy these hard-to-control weeds and weeds. Another disadvantage in the use of these agents as herbicides is that they are tolerated only by cereal crops

and other crops, such as corn and sugarbeet.

Object of the invention

The proliferation of grass weeds in crop and maize crops, such as hawthorn, field saxifrage, and millet, requires new remedies that will satisfactorily solve the variety of weed and weed problems that are occurring.

The aim of the invention is to develop new herbicidal agents which effect improved weed control at low application rates, can be used with good crop tolerance in the pre-emergence and postemergence process, do not damage the crops and which economically meet the current requirements of use in agriculture.

Explanation of the essence of the invention

This object is achieved according to the invention in that the novel herbicidal compositions are suitable for the selective control of monocotyledonous and dicotyledonous weeds in the preemergence and postemergence processes, preferably in cereal, maize and sugar beet crops, and as active ingredient components in addition to compounds of general formula I or their tautomeric forms,

in which R ¹ and R ^{2 may be} identical or different and are H, alkyl (Ci-C ₄ ), cycloalkyl (C ₆ ) or an aryl radical substituted by Cl or CH ₃ O, as additional components

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

1,3-dimethyl-1- (benzthiazol-yl-2 '-) urea (V),

2,4-dichlorophenoxyacetic acid (VI),

1-butylamino-i-dibutoxyphosphonyl-cyclohexane (VII),

S-cyclohexyl-S ^ -trimethylen-uraciKVIN)

S-methoxycarbonylaminophenyl-P'-methylpheny-O-carbamate (IX),

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

2-Chloro-4,6-bis (ethylamino) -1,3,5-triazine (III)

contain.

The preparation of the active compounds of the general formula I can be carried out according to known instructions from the literature / D. Martin, H. Graubaum, J. prakt. Chem.321.315 (1979) /.

The following obtained in this way 2-substituted 4-oxo-i, 2,3,4-tetrahydro-1,3,5-triazino (1,2-a) benzimidazoles of the general formula I are listed in Table 1:

Table 1 Active substances of the general formula I.

connection R ¹ 1.1 H I / 2 H I / 3 CH ₃ I / 4 CH ₃ I / 5 C2H5 I / 6 CH ₃ I / 7 C ₆ H ₅ I / 8 H I / 9 H

R ²

Fp ( ⁰ C)

H 210 nC ₃ H ₇ 214-215 CH ₃ 218 C ₂ H ₈ 200-202 C ₂ H ₅ 211-213 C ₆ HHC 230 H 212-214 (4 (-CH ₃ OC ₆ H ₄ 211-213 (2 (-CI-C ₆ H ₄ 215

It has been found that these novel drug combinations have a particularly broad and selective herbicidal activity in crop plants. As cereals, corn and sugar beets have. Particularly noteworthy here is the very good herbicidal action against hard-to-control weeds, such as Klettenlabkraut (Galium aparine) and Saatwucherblume (Chrysanthemum segetum), as well as against hard-to-control weeds, such as Windhalm (Apera spica-venti), Ackerfuchsschwanzgras (Alopecurus myosuroides) and Barnyardgrass (Echinocloa crus-galli). It is of particular advantage that these active compound combinations according to the invention in crops of cereals, maize and

Beet be used, while only the compounds of general formula I are tolerated only by the cereal crops and other crops crops such as corn and sugar beet suffer because of the necessary high application rates damage.

Surprisingly, the effectiveness of the active compound combinations according to the invention is significantly higher than the sum of the individual components, which is not only an effect supplement, but whose cause is due to a proven by the method of COLBY true synergistic effect.

This synergistic effect is particularly strong in certain combination ratios.

The weight ratios of the active ingredients in the drug combinations can vary in relatively large areas.

10.1 to 3 parts by weight, but preferably between 0.1 and 1 part by weight of active compound of the names II to IX, generally account for 1 part by weight of active compound of the general formula The application of the herbicide combinations is advantageously carried out in the customary for weedkillers preparation or Ausringungsformen, such as solutions, emulsions, suspensions which prepares with the addition of liquid and / or solid carriers or diluents usually with the addition of surfactants and other formulating agents and for use with Water can be diluted.

The application forms depend on the intended use. In any case, they have to ensure a fine distribution of the active substances. The preparation of the preparations is carried out in a conventional manner by mixing or milling.

The following examples are intended to illustrate the present invention without limiting it.

embodiments

To demonstrate the herbicidal activity of the combinations according to the invention, a large number of experiments were carried out. These were applied both in the greenhouse and on arable land in crop stands of cereals, corn and sugar beet. The use of the combinations according to the invention was carried out before emergence or after emergence of the crop plants and the monocotyledonous and dicotyledonous weeds. The evaluation of the control success and the compatibility was made after the notes 1 to 9. Where:

Boniturnote injury in%

95-100 Bigg (Hordeum vulgar) = Active substances of the general formula I. 85-94 winter wheat (Triticum aestivum) = 2-methylmercapto-4,6-bis (isopropylamino) -1,3,5-triazine ^ O- 84 winter roe (Sea ale cereale) = 2-chloro-4,6-bis (ethylamino) -1,3,5-triazine ^ 5- 69 Corn (Zea mays) = 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine 45-54 sugar beet (Betavulgaris) 30-44 Windhalm (Apera spica-Venti) 15-29 Foxtail grass (Alopecurus myosuroides) 5-14 barnyardgrass (Echinocloa crus-galli) 0-4 Blood-red crabgrass (Digitaria sanguinalis) 1 The following listed crops and weeds or Annual panicle (Poaannua) 2 Combat success and compatibility used: Ivy-leaved honorary prize (Veronica hederifolia) 3 A = chickweed (Stellaria media) 4 B = cleavers (Galiumaparine) 5 C = Real chamomile (Matricaria chamomilla) 6 D = buckwheat (Fallopia convolvulus) 7 E = field pansy (Violatricolor arvensis) 8th F = Thlaspi arvense (Thlaspi arvense) 9 G = Shepherd's purse (Capsella bursa-pastoris) H = charlock (Sinapis arvensis) I = White goosefoot (Chenopodium album) K = Krummer Foxtail (Amaranthus retroflexus) L = corn marigold (Chrysanthemum segetum) M = galinsoga (Galinsoga parviflora) N = They are identified by the letters in the following tables. O = The following tables also mean: P = I Q = Il R = III S = IV T = U = V = W = X =

V = 1,3-dimethyl-1- (benzthiazol-yl-2 '-) urea

VI = 2,4-dichlorophenoxyacetic acid

VII = i-butylamino-i-dibutoxyphosphonyl-cyclohexane

VIII = a-cyclohexyl-S-trimethylene-uracil

IX = S-methoxycarbonylaminophenyl-O'-methylpheny-O-carbamate

Table 2: Herbicidal action of the combinations according to the invention against the indicated monocotyledonous and dicotyledonous weeds in winter wheat and winter rye during pre-emergence application (field trial)

active substance

Application rate kgAS / ha

Planting culture B C

weeds

weeds

untreated control

(known)

(known)

1/3 (known)

1/3 + 11 + 111 (according to the invention)

1/3 + V (according to the invention)

0.30 + 0.12

0.60 + 0.24

0.70

1.40

2.10

2.00

3.00

5.00

2.00 + 0.30 +

0.12

3.00 + 0.30 +

0.12

2,00 + 0,70

3.00 + 0.70

2.00 + 1.40

9 9 9 9 9 9 9 9 9 9 9

9 9 9 9 9 9 9 9 9 9 9

9 7 4 7 4 2 6 6 5 3 1

9 3 1 6 5 3 5 5 3 1 1

9 5 3 6 3 1 6 3 2 1 1

9 6 3 5 3 2 5 4 3 3 1

9 4 2 6 4 3 4 3 2 2 1

Table 3: Herbicidal action of the combinations according to the invention against the indicated monocotyledonous and dicotyledonous weeds in winter wheat and winter barley in postemergence application (field trial)

active substance

Application rate kgAS / ha

Crops A B

Weed grass F

Weeds N

untreated control

(known)

VII (known)

I / 3 (known)

I / 3 + Vl (according to the invention)

1/3 + VII (according to the invention)

0.50

0.70

1.35

0.30

0.50

1.00

2.00

2.00

3.00

5.00

2.00 + 0.50

2,00 + 0,70

3.00 + 0.50

2,00 + 0,30

2.00 + 0.50

3,00 + 0,30

3.00 + 0.50

9 9 9 9 9 9 7 5 9 9 9 9 9 9 9 9 9 9

9 9 9 9 9 9 7 6 9 9 9 9 9 9 9 9 9 9

9 9 9 8 9 δ 7 6 6 5 2 4 3 3 4 3 3 2

9 8 7 5 6 4 2 1 8 7 1 3 2 2 3 2 2 2

9 9 9 7 8 δ 6 4 6 5 1 3 3 2 3 3 2 1

9 5 2 1 7 6 4 2 4 2 1 1 1 1 2 1 1 1

9 4 2 1 6 5 2 1 5 3 1 1 1 1 1 1 1 1

Table 4: Herbicidal action of the combinations according to the invention against the indicated monocotyledonous and dicotyledonous weeds in maize in postemergence application (field trial)

active substance application rate Cultivated weeds I weeds V P T kg AS / ha plant 9 9 9 9 D H 9 X 6 7 2 untreated control - 9 9 9 9 3 CJL 1 Vl 0.50 9 9 8th 7 2 4 1 (known) 0.70 9 δ 9 4 7 7 3 1.35 9 8th 8th 1 6 5 2 IV 0.30 9 8th 7 (known) 0.70 9 8th 3

application rate Culture weeds I weeds V -5- 242,340 active substance KGAs / ha plant 7 3 D H 6 X cn 1.00 9 7 5 2 4 P T 2.00 9 5 4 4 3 3 1 1.4 3.00 9 4 5 3 1 7 1 (known) 4.00 9 3 3 2 2 5 1 2,00 + 0,70 9 4 2 2 1 3 1 1/4 + Vl 3.00 + 0.50 9 3 3 1 1 2 1 (Invention) 3.00 + 0.70 9 2 4 1 2 1 1 2,00 + 0,70 9 2 2 1 1 1 1 1/4 + IV 3,00 + 0,30 9 3 1 1 1 (Invention) 3.00 + 0.70 9 2 1 1 1 1 1

Table 5: Herbicidal action of the combinations according to the invention against the indicated monocotyledonous and dicotyledonous weeds in sugar beet in postemergence application (greenhouse experiments)

active substance application rate Cultivated L KGAs / ha plant e K untreated control - 9 9 VIII 0.30 9 7 (known) 0.50 9 4 0.80 9 2 IX 0.30 9 8th (known) 0.50 9 5 1.00 9 2 I / 5 2.00 9 6 (known) 3.00 9 5 4.00 8th 3 1/5 + VIII 2.00 + 0.50 * 9 2 (Invention) 3,00 + 0,30 9 2 3.00 + 0.50 9 1 1/5 + IX 2.00 + 0.50 9 2 (Invention) 3,00 + 0,30 9 3 3.00 + 0.50 9 1

weeds

weeds

9 9 9 8 8 8 7 6 5 3 4 3 2 3 2 2

9 8 7 6 4 3 1 5 4 3 3 2 1 1 1 1

It can be seen from the examples that the individual active compounds have weaknesses when used alone in the herbicidal action. Surprisingly, the combinations according to the invention have the advantage of simultaneously controlling monocotyledonous and dicotyledonous weeds at lower total application rates.

A true synergistic effect is always present in herbicides when the herbicidal action of active ingredient combinations is greater than the sum of the effect of the individual applied active ingredients.

To determine the synergistic effect, the expected effect for a combination of two herbicides according to Colby, S.R., in "Calculating synergistic and antagonistic responses of herbicidal combinations" in Weeds 15 (1), 20-22 (1967), was calculated as follows:

If X =% damage by herbicide A at pkg / ha application rate, Y =% damage by herbicide B at qkg / ha application rate

and Er = the expected damage to the herbicides A and B at ρ and q kg / ha mean application rates, then the expected damage is

E ₁ , = X + Y - X * Y

^Λ 100

If the actual damage E _{1 is} greater than the calculated Er, then the combination is over-additive in its effect, ie there is a true synergism (E ₁ > E _R ).

If E ₁ = Er, then the effect is additive.

If E ₁ <Er, then there is an antagonistic effect.

From one example, in parallel to the calculations in tests, the actual damage to blood red finger millet (I) and to the crooked foxtail (V) in maize cultures was determined.

Table 6: Determination of the synergistic effect in the control of blood red crayfish and crooked foxtail in corn in postemergence application

1 gef. = Damage

2 calc. = The injury calculated according to the formula given by Colby

active substance application rate Cultivated Damage in% in I about ²¹ Damage in% in V about ²¹ KGAs / ha D gef. ¹¹ gef. ¹ » Vl 0.50 0 0 40 (known) 0.70 0 0 80 1.35 0 10 90 IV 0.30 0 0 20 (known) 0.70 0 10 40 1.00 0 20 80 I / 4 2.00 0 40 50 (known) 3.00 0 50 40 60 90 4.00 0 60 50 80 76 1/4 + Vl 2,00 + 0,70 0 50 50 100 92 (Invention) 3.00 + 0.50 0 80 46 90 70 3.00 + 0.70 0 90 50 100 68 1/4 + IV 2,00 - 0,70 0 80 55 100 76 (Invention) 3,00 + 0,30 0 60 90 3.00 + 0.70 0 90 100

Claims (9)

Invention claim: 1. A herbicidal composition for the selective control of monocotyledonous and dicotyledon weeds in the preemergence and postemergence process, preferably in cereal, maize and sugarbeet crops, characterized in that they contain compounds of the general formula or their tautomeric forms in addition to customary excipients and carriers where R ¹ and R ^{2 may be the} same or different and denote H, alkyl (C ¹ -C ₄ ), cycloalkyl (C ₆ ) or an aryl radical substituted by Cl or CH ₃ O, and contain one or more additional components. 2. A herbicidal composition according to item 1, characterized in that 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine are used as an additional component. 3. A herbicidal composition according to item 1, characterized in that is used as an additional component, 1,3-dimethyl-1- (benzthiazol-yl-2 ') - urea. 4. A herbicidal composition according to item 1, characterized in that 2,4-dichlorophenoxyacetic acid is used as an additional component. 5. A herbicidal composition according to item 1, characterized in that is used as an additional component 1-butylamino-idibutoxyphosphonylcyclohexan. 6. A herbicidal composition according to item 1, characterized in that is used as an additional component S-cyclohexyl-S ^ trimethyleneuracil. 7. A herbicidal composition according to item 1, characterized in that 3-methoxycarbonylamino-phenyl- (3'-methylphenyl) carbamate is used as an additional component. 8. A herbicidal composition according to item 1, characterized in that as additional components 2-methylmercapto-4,6-bis (isopropylamino) -i, 3,5-triazine and 2-chloro-4,6-bis (ethylamino) 1,3,5-triazine can be used. 9. A herbicidal composition according to item 1, characterized in that the weight ratio of the active compounds of the general formula to the additional components 1: 0.1 to 1: 3, preferably between 1: 0.1 to 1: 1.