PL103511B1 - A WORMHOUSE - Google Patents

Description

The present invention relates to a herbicide for the destruction of glucocorticoid oats in cereal crops.

The deaf oat (Avena fatua) is the most widespread weed in the world and is growing in size threatening crops and causing serious losses.

A well-known group of compounds showing a strong destructive effect on deaf oats and a clear selectivity in relation to cereals there are N, N-disubstituted derivatives of alanine, occurring, for example, in a herbicide under the name "SuffiK" when used in wheat or "Barnon" when used in barley.

From the German patent specification No. 2333414 three-component herbicidal mixtures are known containing, in addition to two herbicides, N, N-disubstituted alanine derivative, showing a synergistic effect in the destruction of deaf oats. However, the killing of weeds on a large scale by three-component means is relatively expensive, however, in the cited description, there is no information regarding two-component measures.

Although German patent description No. 2336444 mentions a mixture consisting of bentazone (i.e. 3-isopropyl-1H, 2,1,3-benzothiazin- (4 (3H-one) ibenzylprop-ethyl (N-3,4-dichlorophenyl) 2.2-dioxide Ethyl N-benzoylamino-propionate) with a synergistic effect in the destruction of glucocorticoid oats, but no mentions or suggestions about the selectivity of such a mixture with respect to cereal crops.

It has now surprisingly been found that a synergistic two-component mixture can be obtained destroying deaf oats and at the same time having high selectivity in relation to cereals.

According to the invention, the herbicide contains as active ingredients 3-isopropyl-2,2-dioxide lH-2, l, 3-benzothiazin- (4), 3H-one and a N, N-disubstituted alanine derivative of the general formula I, wherein Y is chlorine, Z is fluoro, X is oxygen or sulfur, and R is -ORi, in which Ri is hydrogen, a salt-forming metal, or an ammonium ion optionally substituted an alkyl, optionally substituted alkyl, cycloalkyl, aryl, alkenyl or alkylaryl group, or represents a group -SR2, wherein R2 is optionally substituted alkyl, cycloalkyl, aryl, alkenyl or alkylaryl, or represents a group -NR3R4 or -ON = CR3R4, where R3 and R * independently represent a hydrogen atom, a hydroxy group, an optionally substituted alkyl, alkenyl, aryl group, 2 103 511 alkylaryl, heterocyclic, alkoxy, alkylthio or amino, or R3 and R4 taken together are polymethyl- new, which may contain one or more heteroatoms in the carbon chain.

In the following, and in the examples, 3-isopropyl-1H-2, 1,3-benzothiadiazin- (4), 3H-one 2,2-dioxide will be abbreviated as dioxide.

The preferred substituents of the alanine derivative, in addition to the aforementioned chlorine and fluorine, are the alkyl group with 1-4 carbon atoms or alkoxy group with 1-4 carbon atoms. With suitable alkyl, alkenyl- In the formula I, alkoxy, alkylthio groups have up to 6 carbon atoms. Relevant groups aryl, alkylaryl, cycloalkyl, heterocyclic and polymethylene are groups containing up to carbon atoms, preferably up to 7 carbon atoms. As heteroatoms in a polymethylene or heterocycle - it deals with oxygen, nitrogen or sulfur atoms, preferably one or two oxygen and / or nitrogen atoms. myfctadr N, N-disubstituted alanine derivatives of the formula I and methods for their preparation can be used found in the following German DOS patents No. 1643527, Germany DOS No. 2109910, Germany DOS no.2303029, RIN DOS no.2349970, RFN DOS no.2504319, RFN DOS no.2460691.

SzCzigBfofe, preferred alanine derivatives are compounds of the general formula II, in which Y and Z have higher as defined and R represents a hydrogen atom or an alkyl group of up to 6 carbon atoms, e.g. methyl, ethyl or isopropyl. Among these compounds, one of the most beneficial substances for the destruction of gluche oats in barley crops is a compound of general formula 2, where R is gripe isopropyl. One of the most preferred active ingredients for use in wheat crops is the compound Formula 2 wherein R is methyl.

Alanine derivatives can exist in optically active forms and generally take the most the left-handed isomer is active. Where appropriate, the alanine derivative may be used inside according to the invention in its most active form.

The tests carried out on the herbicide according to the invention at various doses show that it has a synergistic effect in relation to gluco oats. This is an unexpected statement to the the fact that one of its active ingredients, i.e. dioxide, does not have a destructive effect against deuche oat. Besides, despite the increased destructive effect in relation to deaf oats, the agent according to the invention, it essentially shows no greater effect than that of cereals, so that it can be safely used as a selective herbicide for the destruction of glucy oats in cereal crops.

The invention allows the destruction of deaf oats in cereal crops at various stages of development by applying it to foliage after emergence. Deaf oats can be destroyed in cereal crops with use the agent at a dose of 0.25 to 2.0 kg / ha, in which the weight ratio of alanine derivative to dioxide is 10.2 to 1:25, preferably 10.5 to 1:15.

The herbicide according to the invention may contain a carrier, surfactant or both of these additions. This makes it easier to use the agent in the desired doses in areas infested with deaf oats. The term "carrier" as used herein means a solid or liquid, organic or inorganic substance synthetic or of natural origin.

Typical solid carriers are natural and synthetic clays and silicates, e.g. natural silicas, such as diatomaceous earths, and aluminosilicates such as kaolinity, montmorillonites and mica. Typical liquid carriers are ketones, e.g. methylcyclohexanone, aromatic hydrocarbons, e.g. methylnaphthalenes, petroleum fractions such as petroleum xylenes and light mineral oils and chlorinated hydrocarbons such as e.g. carbon tetrachloride. Mixtures of liquids are often suitable.

The agent may contain one or more surfactants and / or binders. As a substance The surfactant may be an ionic or non-ionic emulsifying, dispersing or agent moisturizing. The agent may contain any surfactant conventionally used in compositions herbicides or insecticides. Examples of suitable surfactants are salts sodium or calcium polyacrylic acids and lignosulfonic acids, acid condensation products fatty or aliphatic amines or amides with at least 12 carbon atoms in the molecule with ethylene oxide and / or propylene oxide; fatty acid esters with glycerin, sorbitol, sucrose or pentaerythritol, their condensates with ethylene and / or propylene oxide; condensation products of fatty alcohols or alkylphenols, e.g. p-octylphenol or p-octylcresol, with ethylene oxide and / or propylene oxide, sulfates or sulfonates of these condensation products, alkali or alkaline earth metal salts, preferably sodium salts of sulfuric or sulfonic acid esters with at least 10 carbon atoms in the molecule ce, e.g. sodium lauryl sulfate, sodium H-alkyl sulfates, sodium salts of sulfonated castor oil and sodium alkylarylsulfonates such as sodium dodecylbenzene sulfonate, and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.

The invention also includes aqueous dispersions and emulsions, obtained e.g. by diluting with water a wettable a powder or a concentrate according to the invention. They can be water-in-oil or oil-in-water emulsions, and they can have a consistency similar to mayonnaise r 103511 3 The agent according to the invention can be used in conventional ways. Dust and liquid agent can be used use with a dust sprayer, belt sprayer, manual sprayer and dust sprayer. That Due to the effectiveness of the agent in small doses, it can be sprayed from an airplane, in the form of dust or liquid.

If desired, the inventive agent can also be mixed with another deaf-destroying agent oats such as 4-chloro-2-butynyl-m-chlorocarbanilate, known as barban (proprietary name "Carbyne"), Methyl 2-chloro- 3- (4-chlorophenyl) propionate (chlorphenprop methyl, proprietary name "Bidisin") or methyl- 1,2-Dimethyl-3,5-diphenylpyrazolium sulfate (proprietary name "Avenge").

In order to obtain a broader spectrum of action, especially against broadleaf weeds, According to the invention, it can be mixed with suitable herbicides exhibiting an effect destructive broadleaf weeds, but selective in relation to cereal crops. Examples of such selective broadleaf weed killers are derivatives of fencksalkane carboxylic acid of the general formula 3, in which X * represents a chlorine atom or a methyl group, Y * represents a chlorine atom, Z 'represents hydrogen or chlorine atom, A is an alkylene group with 1-4 carbon atoms, and R 'is a carboxyl group, and their salts and esters. These are, for example, the following acids: 2,4-dichlorophenoxyacetic, (± / -2 72,4-dichlorophenoxy / pro vertical, 4-chloro-2-methylphenoxyacetic, (± / -2- / 4- chloro-2-methylphenoxy / propionic and 4- / 4- chloro-2-me- tylophenoxy / butyric.

The invention is illustrated by the following examples in which the effect of the agent according to the invention has been demonstrated: for deaf oats (Avena fatua) in oats (Avena sativa). Based on experience in this field it was found that the data obtained in such experiments in oat crops are fully representative under in terms of the action on deaf oats and because of their repeatability.

Example I. The following mixture was tested: A) Dioxide in the form of 48% emulsifying concentrate, i.e. the herbicide known under the trade name Basagran and B) N-benzoyl-N- (3-chloro-4-fluorophenyl) - Isopropyl 2-aminopropionate in the form of a 20% emulsifying concentrate, a herbicide known under trade name Barnon.

In pots with a diameter of 7 cm with compost soil John Innes No. 1, 25 to 30 barley seeds were sown and seed of cultivated oats (Avena sativa). When the plants had reached the 1 to 1.5 leaf stage, they were sprayed solution of the tested mixture, with five different doses used for each species with the logarithmic dilution scale. They were also sprayed with mixtures of five different proportions of compounds.

The tests were carried out 11 days after spraying. Phytotoxicity of barley and oats were assessed visually (barley- on a scale of 0 to 9, oats and oats- on a percentage scale where 100 is no development after spraying). These values are expressed as a percentage of the values for barley and oats untreated, were analyzed on a digital machine in order to calculate the inhibition doses development and determining a 50% reduction for barley and a 90% reduction for oats, which are in short respectively as DZR50 barley andDZR90 oats. Selectivity index (W?) For the tested compound is calculated from the formula: WS = DZRS0 barley / DZR90 oats.

The value of the selectivity coefficient is a measure of the selectivity of the herbicidal action of the subjects mixtures or compounds. The greater the value of the selectivity factor, the better the selectivity action between two plant species.

The composition of the mixtures used and the results obtained are given in Table I.

Table I Factor DZR50 (kg / ha) DZR90 (kg / ha) selectivity (B) :( A) for (B) for (B) DZR50 barley / barley oats DZR90 oats 0: 1 1: 4 1: 2 1: 1 1: 0.5 1: 0 2.12 0.12 18 2.48 0.09 28 2.81 0.10 28 3.69 0.09 41 3.67 0.14 264 103 511 These results indicate that the dioxide (Compound A) as such has no effect on the oats and even in combination with The ester of alanine (Compound B) gives oats DZR90 values lower than that of Compound B alone. hence that component A has a certain interaction effect. You can also state that the factor selectivity improves rather than deteriorates.

Example II. The following mixture was tested: (A) Dioxide in the form of a 48% emulsifying concentrate go, i.e. the herbicide known under the trade name Basagran and C) N-benzoyl-N- (3-chloro-4-fluorophen- methyl lo) - 2-aminopropionate in the form of a 15% emulsifying concentrate.

The experiment described in Example 1 was repeated except that seeds were used instead of barley seeds wheat.

The results are given in Table II.

(MOTH) 0: 1 1: 8 1: 4 1: 2 1: 1 130 T. DZR10 (kg / ha) for (C) wheat 1.00 0.72 1.01 0.84 0.62 a b 1 i c a II DZR9o (kg / ha) for (C) oat 0.09 0.07 0.06 0.07 0.08 Factor selectivity DZRj about wheat / DZR9o deaf oats at 17 12 8

Claims (3)

Patent claims 1. A herbicide containing active substances and a solid or liquid carrier, characterized in that the active substances are 3-isopropyl-1H-2, 1,3-benzothiadiazin- (4), 3H-one and N 2,2-dioxide, N-disubstituted alanine derivative of the general formula I, in which Y is a chlorine atom, Z is a fluorine atom, X is an oxygen or sulfur atom, and R is a group of the general formula -ORi, in which Rt is a hydrogen atom, a salt-forming metal atom or an ammonium ion, optionally substituted alkyl, optionally substituted alkyl, cycloalkyl, aryl, alkenyl or alkylaryl, or is a group of the general formula -SR2 where R2 is optionally substituted alkyl, cycloalkyl, aryl, alkenyl or alkylaryl, or is a group of the general formula -NR3R4 or -ON = CR3R4, where R3 and R4 are independently hydrogen, hydroxy, optionally substituted alkyl, alkenyl, aryl, alkylaryl, heterocyclic, alkoxy, alkylthio or amine These or R3 and R4 together represent a polymethylene group optionally containing one or more heteroatoms in the carbon chain, the weight ratio of the alanine derivative of the formula 1 to 2,2-dioxide 3-isopropyl-1H-2, 1,3-benzothiadiazin- ( 4), the 3H-one ranges from 1: 0.2 to 1:25. 2. The measure according to claim A compound according to claim 1, characterized in that the alanine derivative is a compound of formula I, in which X is oxygen, Y is chlorine, Z is fluoro, and R is isopropoxy. 3. The measure according to claim The compound of claim 1, characterized in that the alanine derivative is a compound of formula I, in which X is oxygen, Y is chlorine, Z is fluoro, and R is methoxy. 103 511 H XH-COR YI CH3 Formula 1, CO- / ~ S zAn (\ - / / CH-COOR, CBa Pattern 2 • - / V-0-AR 'Z * Pattern 3