DD294167A5 - HERBICIDE MEDIUM - Google Patents

Abstract

The invention relates to herbicidal compositions for the control of monocotyledonous and dicotyledonous weeds in agricultural and agricultural crops such as cereals, maize, sugarbeet, potatoes, onions, carrots and legumes in the pre-emergence and / or postemergence process. As active ingredients, the new agents contain, in addition to conventional adjuvants and tracer substances, substituted * The use of the new compositions is particularly advantageous against heavily-susceptible weeds and weeds, which can be fought simultaneously. {Herbicidal agents; agricultural and agricultural cultures; combating; mono- and dicotyledonous weeds; Pre- and post-emergence procedures; Kulturpflanzenvertraeglichkeit; agents; *}

Description

in the R ¹ = lower alkyl

and R ² = alkyl, aralkyl or cycloalkyl

mean, included.

Field of application of the invention

The invention relates to non-herbicidal agents for controlling monocotyledonous and dicotyledonous weeds in agricultural and horticultural crops, in particular in cereals, maize, root crops, legumes and vegetables.

Characteristic of the known state of the art It is well known that the proliferation of hard-to-control weeds and weeds requires new resources that will increase the diversity of

solving problems in an equally satisfying way. The means known in the literature for destroying hard-fought weeds and weeds have some disadvantages, such as non-universal substitutability or non-crop tolerance. Thus, for example, by a specific use of a combination of 2- (2-methyl-4-chlorophenoxy) propionic acid (mecoprop, MCPP) and 3,5-Dljod-4-hydroxy-benzonitrile (loxynil) in

Grain crops are various heavyweight weeds, especially velvetleaf and chamomile, compared to

sole use of mecoprop can be better controlled, which is due to an improvement in the initial effect (GB-PS 822199, DE-AS 1266563, G.Feyerabend and W. Kramer, Feldwirtschaft No.3, p.121 to 124 [1973].

However, this combination has the disadvantage that monocot weeds are not combated. Furthermore, it is known that by the use of dimethyl-1- (benzthiazolyl-2) urea (Methabenzthiazuron) one-year Ungräser, such as Windhalm be combated in the wake process (DE-AS 1542789). The hard-to-control weeds, such as burdock and seedweed, show some resistance

opposite the methabenzthiazuron.

It is also known that substituted imidazole derivatives have herbicidal and growth-regulatory properties. So

are in DE-PS 2732531 N-benzhydryl or N-trityl-imid-azolcarbonsäuren and their derivatives as compounds with herbicides

Effectiveness-especially in Vorauflaufverfahren- described. U.S. Patent 4,565,875 claims, inter alia, 4-substituted imidazole-5

carboxylic acid derivatives as active ingredients with growth-regulatory properties.

Object of the invention

The aim of the invention is to develop new herbicidal agents with selective action, which can be used in agricultural and horticultural crops in pre- and post-process and have a broad spectrum of activity against the wild plants occurring in these crops. ;

Explanation of the essence of the invention

The object of the invention is to find new Imidazolcarbonsäureester with herbicidal activity, which are characterized by a good selectivity and crop plant compatibility. This object is achieved in that the novel selective herbicidal agents in addition to conventional excipients and carriers as active ingredients imidazole-4,5-dicarboxylic acid ester of the general formula

-C00R ¹

COOR ¹ ι ρ »

R ^

R ¹ = lower alkyl and R ² = alkyl, aralkyl or cycloalkyl,

contain.

The preparation of the novel herbicidal compositions according to the invention underlying active ingredients is carried out by oxidative Desulphurization of corresponding N-substituted 2-mercaptoimidazole-4,5-dicarboxylic acid esters with dilute nitric acid

or by N-alkylating the corresponding imidazole-4,5-dicarboxylic acid esters with alkyl halides.

The novel herbicidal compositions according to the invention are very suitable for controlling monocotyledonous and dicotyledonous Weeds without crops of cereals, corn, potatoes, sugar beets, carrots, onions and legumes

damage. They can be used in the pre-emergence and post-emergence processes and, because of their selective action, are superior to known herbicidally active compounds with a related chemical structure.

Particularly noteworthy is the very good effect against schwärekärrpffbare weeds, such as the Klettenlabkraut, Seedwort and chamomile species, as well as hard-to-control grass weeds, such as millet and hawthorn. From

It is particularly advantageous that such often difficult to control weeds and grass weeds with the invention

Active ingredients of the general formula are simultaneously controlled, including known herbicides from the prior art not in

are able. These advantages outweigh the disadvantage of relatively higher application rates compared to those already described

Herbicides. Another valuable feature is the rapid decay of the herbicidal effect, so that also on replicate cultures

no damage occurs.

The herbicidal compositions of the invention thus represent an enrichment of the prior art. The application of these new herbicidal agents is conveniently carried out in the usual for weed control Formulation or application forms, such as solutions, emulsions, suspensions, with the addition of liquid and / or

solid carriers or diluents, usually with the addition of surface-active substances and others

Formulation aids can be prepared and diluted with water for use. Set the application forms

depending on the purpose. In any case, they have to ensure a fine distribution and * of the active substances.

The preparation of the preparations is carried out in a conventional manner by mixing or milling. The formulations thus prepared generally contain between 0.1 and 95 parts by weight in% of active ingredient,

preferably between 0.5 and 90 parts by weight in%. Depending on the purpose and type of application, the

Application rates vary, for example between 1 and 10 kg / ha of active substance, preferably between 2 and 5 kg / ha Active substance. embodiments The active compounds according to the invention are listed in Table 1. Table 1 Inventive active compounds of the formula

N ifCOOR ¹

H Il ₁

COOR ¹

No. R ¹ R ² KpCC / TorrJbzw.FpfC)

1 C ₂ H ₆ CH ₃ 159-161 / 0.7 2 C ₂ H ₆ C ₂ H ₆ 155-156 / 0.6 3 C ₂ H ₆ nC ₃ H ₇ 151-153 / 0.2 4 C ₂ H ₆ nC ₄ H ₉ 171 / 0.6 5 C ₂ H ₆ ! -C ₄ H ₉ 152 / 0.4 6 CHr ΛΛ 142-144 / 1

C ₂ H ₆ \ / " ^υη 2 Β ⁴ " ⁵⁵ '

For Nachwels the herbicidal activity and the crop plant compatibility experiments were carried out both under greenhouse · and under field conditions.

The following crops, weeds and grass weeds were used to assess tolerability and control success. They are indicated by the given letters.

Table 2 Investigated plant spectrum

A barley Hordeum vulgar B wheat TriticumaestiVum C rye Sea ale cereal D Corn Zea mays e sugar beet Betavulgaris F potato Solanumtuberosum G   carrot Daucuscarota H onions Alliumcepa I peas Pisumsativum K " field beans Vicia faba L Chicken millet ' Echinochloa crus-galli M Windhalm Apera spica-venti N Annual panicle Poaannua O chickweed Stellaria media P Henbit Lamium amplexicaule Q charlock Sinapisarvensis R cleavers Galium Parine _# S White goosefoot Chenopodium album T Thlaspi arvense Thlaspi arvense U Hirtentäschl Capsella bursa-pastaris V Odorless beach chamomile Tripleurospermum inodorum W corn marigold Chrysanthemum segetum X Krummer Foxtail Amaranthus retroflexus

The evaluation of the control success and the compatibility was made after the notes 1 to 9. Mean

Boniturnote Damage in% 1 95-100 2 85-94 3 70-84 4 55-69 5 45-54 6 30-44 7 15-29 8th 5-14 9 0-4

In the following tables mean I drug no. 3 (according to Table 1) II Active ingredient No. 4 (according to Table 1) III Active ingredient No. 5 (according to Table 1) IV Drug # 6 (according to Table 1)

V SYS67 Actril C (active ingredients: 4-hydroxy-3,5-diiodobenzonitrile (loxynil) and 2- (2-methyl-4-chlorophenoxy) proplonic acid mecoprop)

VI Pyramln (active ingredient: 1-phenyl-4-amino-5-chloro-pyridazon- (6)) VII Methabenzothiazuron (1: 3-dimethyl-1 - (benzthiazolyl-2 -) - urea VIII Elburon (30% atrazine + 20% fenuron) example 1

Under greenhouse conditions, water-suspended formulations of the active compounds according to the invention were sprayed on plants which were in the cotyledon to four-leaf stage. The application rates were 1 to 5 kg / ha of active substance as a 50% spray powder in 600 l of water per hectare. The final evaluation took place on the 21st day after injection by rating. The results are summarized in Table 3.

Table 3 Effect of compounds of the invention in postemergence application under greenhouse conditions

active substance expenditure 3.0 crops B e • weeds M weeds R U V X mengekg / ha 4.0 A 9 9 L 9 Q 9 9 9 9 control - 5.0 9 9 9 According to the invention: 1.0 9 9 5 6 2 4 2 I 2.0 9 9 9 6 3 3 3 1 3 1 3.0 9 9 8th 4 2 3 2 1 2 1 4.0 8th 9 9 3 7 2 6 1 5 1 Il. 3.0 9 9 9 6 7 2 3 1 3 1 4.0 9 9 9 4 2 2 3 1 2 1 5.0 9 9 6 3 2 2 2 1 1 1 3.0 8th 9 9 2 8th 1 6 1 8th 1 Ill 4.0 9 9 9 6 5 3 3 1 3 1 5.0 9 9 8th 3 2 2 2 1 2 1 8th 9 9 2 8th 2 9 2 8th 2 IV 0.45 + 1.35 9 9 9 6 4th 5 7 1 4 1 0.60 + 1.80 9 9 7 4 2 3 4 1 2 1 2.6 9 3 2 known: 9 - 9 4 2 3 5 V 9 9 - 9 9 1 1 1 1 3 8th - 9 9 5 1 6 2 3 5 Vl - 7 1

From Table 3 it can be seen that Compounds I, III and IV of the invention mono- and dikotyie weeds with 4.0 to 5.0 kg AS / ha sufficiently combat. The compound II according to the invention already has an effect of 2.0 to 3.0 kg AS / ha against mono- and dicotyledonous weeds. The known compounds V and Vl are effective only against dikotyie weeds sufficiently. Surprisingly, the selectivity of the compounds of the invention both in cereals and in beet crops.

Example 2 On open land crops were barley, wheat, rye, corn, potatoes, carrots, onions, peas and field beans

treated. Wheat and rye were in the two-leaf stage at the time of application until the stage of

Tillering. Corn had reached a stature height up to 15cm. Potatoes, carrots, onions, peas and field beans were added Application not yet accumulated. The majority of the weeds were in the cotyledon stage until the beginning of the stage Bud formation or tillering. The application rates were 2.0 to 5.0 kg of active ingredient per hectare as 50% Spray powder in 600I of water per hectare. The results obtained are shown in Tables 4,5 and 6. Table 4 Effect of the compounds according to the invention against mono- and dicotyledon weeds in post-emergence cereals

active substance expenditure 2.0 crops B C weeds N weeds P R T W mengekg / ha 3.0 A 9 9 M 9 O 9 9 9 9 control _ 4.0 9 ä 9 According to the invention: 4.0 9 9 3 3 3 2 2 Il 4.5 9 9 9 6 2 4 2 2 2 2 5.0 9 9 9 2 1. 2 1 1 1 1 9 9 9 1 4 1 4 5 3 3 I 0.45 + 1.35 9 9 9 5 2 3 2 3 3 1 0.60 + 1.80 9 9 9 3 1 2 1 3 1 1 1.75 9 2 2 known: 2.10 9 9 9 6 2 2 7 V 2.80 9 9 9 9 8th 3 3 1 1 5 9 9 9 9 3 2 3 8th 2 8th VII 9 9 9 β 2 4 3 7 1 β 9 9 .9 3 1 2 1 5 1 4 7 1 1

It can be seen from Table 4 that both dicotyledonous and monocotyledonous weeds are simultaneously controlled by the novel compounds of the present invention.

In contrast, the combination of loxynil and mecoprop (V) does not combat monocotyledonous weeds. Compound VII (methabenzthiazuron) causes slight damage to barley. In addition, the seedwort flower is damaged only insufficiently by both known compounds (V and VII).

Table 5 Effect of the compounds according to the invention against monocotyledonous and dicotyledonous weeds in maize in post-emergence application

active substance • expenditure Culture weeds N weeds P Q S X mengekg / ha D L 9 O 9 9 9 9 control known: _ 9 9 9 According to the invention: VIII " 2 2 2 3 2 Il 2.0 9 3 2 3 2 1 2 1 3.0 9 3 1 2 1 1 1 1 4.0 9 1 1 7 2 3 4 6 0.45 + 0.30 9 8th 4 5 1 1 3 4 0.60 + 0.40 9 5 3

From Table 5 it can be seen that of the inventive compound II both the grass weeds, such. B. millet, as well as weeds, such as Krummer foxtail, with application rate from 2.0 kg AS / ha are combated simultaneously. The known combination VIII is inadequate against grass weeds.

Table 6

Effect of the compounds according to the invention against monocotyledonous and dicotyledonous weeds in potatoes, carrots, onions, peas and field beans in a treatment before emergence of the crop plants but after emergence of the weeds and weeds

Active ingredient effort control Culture G H I weeds L N weeds P Q R S U X mengekg / ha According to the invention: F 9 9 9 K 9 9 O 9 9 9 9 9 9 Il 2.0 9 9 9 3.0 9 9 9 2 2 2 1 4 2 1 1 4.0 9 9 9 9 9 1 1 2 1 1 3 1 1 1 III 3.0 9 9 9 9 9 1 1 2 1 1 2 1 1 1 4.0 9 9 9 9 9 4 3 1 3 1 7 4 1 2 5.0 9 9 9 9 9 2 3 3 3 1 4 3 1 1 9 9 9 9 9 1 1 2 2 1 2 'I. 1 1 9 9 1

The agents according to the invention, for example the compounds II and III, can be used in slow germs, such as potatoes, carrots and onions, as well as in peas and field beans, before emergence of the crop plants. The already accumulated weeds and weeds are destroyed.

Claims (1)

Herbicidal agents for controlling monocotyledonous and dicotyledonous weeds in agricultural and horticultural crops for use in the pre-emergence and / or postemergence process, characterized in that they contain, in addition to customary auxiliaries and excipients, as active substances, imidazole-4,5-dicarboxylic acid esters of the general formula II COOR ¹ I! l