DE2647165A1 - HERBICIDES AGAINST WILD OATS - Google Patents

Description

Description of the patent application of

Shell Internationale Research Maatschappij B.V. Carel van Bylandtlaan 30, The Hague / Netherlands

concerning
Herbicides against wild oats

The invention relates to a herbicidal agent

to combat wild oats in crops.

Wild oats (Avena fatua) presents an important worldwide weed problem and is increasing in number Dimensions in competition with agricultural crops. As a result, the annual economic losses incurred by the Presence of wild oats occur considerably.

It has surprisingly been found that the activity of a number of known herbicides for control of wild oats in crops can be increased with the help of a methylene-dioxy-benzene derivative, the has hitherto been used exclusively as a synergist for insecticides, especially pyrethrins.

The invention relates to a herbicidal agent comprising as active ingredient one of the following herbicides against wild oats:

709818/1061

(a) 4-chloro-2-butynyl-m-chlorocarbanilate;

(b) methyl 2-chloro-3- (4-chlorophenyl) propionate;

(c) 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate or

(d) 2,4-dichlorophenyl-4- (2-methoxycarbonylethyloxy) phenyl ether

and a methylene-dioxybenzene derivative as a synergistic agent the general formula

(D

in which Y is a hydrogen or halogen atom or an alkyl group, a straight-chain, branched or cyclic polyether group; X is a straight _/ branched chain

or cyclic polyether group, a halogen atom or a cyano, cyanomethyl, hydroxymethyl, mereaptomethyl or an ethynyl group, a group of the formula -CH = NOR (where R is an alkylcarbonyl group), a group of the formula -CH = CH-R ( where R is a pyridyl group), a group of the formula-CONR ² R ³ or ~ CSNR ² R ³ (where R ² and R ^{3 are} each a hydrogen atom or an alkyl, alkoxycarbonylalkyl, aryl or haloaryl group), a group of Formula -CH CH (CH-z) -SO (CH ₂ ) yCH a cycloalkyl group which is substituted by 1 or 2 alkoxycarbonyl groups and / or alkyl groups, a cycloalkanone group optionally substituted by an alkyl and / or alkoxycarbonyl group or one, optionally by Alkyl-substituted cycloalkenylon groups or X and Y together are an alkylene group which is optionally substituted by 1 or 2 alkoxycarbonyl groups and / or alkyl groups.

In the general formula I given above, this is preferably for the methylenedioxybenzene derivatives Halogen atom, a chlorine, bromine and / or fluorine atom, the alkyl, cycloalkyl, alkoxycarbonyl, alkoxycarbonylalkyl,

709818/1061 "^

Cycloalkanol and cycloalkenylon groups preferably contain Ms to 6 carbon atoms, the alkylene chain up to 4 carbon atoms atoms, the aryl group is preferably a phenyl group and the polyether group is an aliphatic group, the Number of oxygen ether bonds in the range from 2 to 6 and die'up to 20 carbon atoms.

Examples of the polyether group are as follows:

CH ₂ . CH ₂ . O) ₂ -C ₄ Hq

O (CH _{2 .CH 2} .O) ₂ -C ₄ H ₉

-CH ₂ O (CH ₂ .CH ₂ .O) ₂ -C ₄ H ₉

-O-CH- (CH ₂ .CH ₂ .O) ₂ -C ₂ H ₅

■ 3,4- / 1-ethylervdioxyphenyl

The study of herbicides against wild oats has a clear synergism in terms of activity against wild oats result when the following methylenedioxybenzene compound is applied:

H ₂ .0. (CH ₂ .CH ₂ .O) ₂ .CH ₂ .CH ₂ .CH ₂ .CH ₃

CH ₂ .CH ₂ CH ₃

709818/1061

Accordingly, herbicidal agents containing one of the herbicides against wild oats (a) to (d) and the specified Methylenedioxybenzene derivative preferred according to the invention.

The only known synergistic effectiveness of these methylenedioxybenzene derivatives relates to their application for insecticides and it is most surprising that they are also synergistic in the herbicide field Effect. Of course, herbicides against wild oats need to have commercial application to be found to be selective in their effects and not to have a lasting adverse effect on the growing Keep crops to which they are applied. As a result, it is with one agent that the herbicide contains, it is important that this balance of selectivity is not affected by a. Interaction with others in that Means existing ingredients is adversely shifted. It is equally surprising that the methylenedioxybenzene synergist while increasing the herbicidal effectiveness against wild oats, it does not cause any adverse effect exerts selectivity in crops. The agents according to the invention can thus be used safely as selective herbicides can be used in crops interspersed with wild oats, always provided that the respective Herbicids carried out according to the usual method of applying herbicides against wild oats will.

According to the invention it becomes possible to develop wild oats in a wide range of its development by applying it to tackle the leaves after emergence. Wild oats can be controlled in crop grain by applying them from 0.1 to 2.0 kg / ha of active ingredient of an inventive Means, being the weight ratio of herbicide against wild oats to methylenedioxybenzene derivative in the range from 10: 1 to 1:10, preferably in the range from 5: 1 to 1: 1 lies.

../5 709818/1061

The herbicidal compositions of the invention can also be a carrier, a surfactant, or both a carrier as well as a surfactant included to facilitate the application of the agent to wild oats to ease contaminated terrain in the desired dose. As used herein, the term "carrier" means a solid or a liquid that is inorganic or organic and synthetic or natural could be.

Typical solid supports include natural and synthetic clays and silicates, e.g., natural silicas, such as diatomaceous earth and aluminum silicates, e.g. Kaolinites, 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, e.g. carbon tetrachloride. Mixtures of liquids are also often suitable.

The agent can contain one or more surfactants and / or tackifiers. The surface-active Agent can be an emulsifying or dispersing agent or a wetting agent. It can be non-ionic or ionic be. Any of the surfactants commonly used in the preparation of herbicides or insecticides can also be applied. Examples of suitable surfactants are Sodium or calcium salts of polyacrylic acids and lignosulfonic acids, the condensation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and / or Propylene oxide, fatty acid esters of glycerol, sorbitol, sucrose or pentaerythritol, condensates of these products with ethylene oxide and / or propylene oxide, condensation products of fatty alcohols or alkyl phenols, e.g. p-Octylphenol or p-Octylcresol, with ethylene oxide and / or

709818/1061

Propylene oxide, sulfates or sulfonates of these condensation products, alkali metal or alkaline earth metal salts, preferably sodium salts ₇ of sulfur or sulfonic acid esters, containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulfate, sodium sec-alkyl sulfates, sodium salts of sulfonated castor oil, and sodium alkylarylsulfonatyl, such as sodium dodeconates and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.

Aqueous dispersions and emulsions such as agents obtained by diluting a wettable powder or a concentrate according to the invention with water, are also within the scope of the invention. These emulsions can be used as water-in-oil or as oil-in-water emulsions are present and have a thick mayonnaise-like consistency.

The invention also relates to a method for the selective control of wild oats in crops, in which an agent according to the invention is applied to an area of land carrying crops and with wild oats is contaminated.

The compositions according to the invention can be applied to the wild oat plants in a conventional manner. the Dusts and liquids can be conveniently applied using powder atomizers, hand or machine spray devices (boom and hand sprayers) etc. are applied. The funds can also be taken from aircraft as dust or spray due to the effectiveness of the agents at low doses.

'In addition, the agents according to the invention can so-called "Hormone" herbicides (the phenoxyalkanoic acid salts and esters, e.g. MCPA, CMPP and 2,4-DP) and / or herbicides against broad-leaved weeds, e.g. Ioxynil, bromoxynil and bentazone.

709818/1061 ·· /?

The invention is illustrated in more detail by the following examples. In these examples, the effectiveness of the invention Means versus cultured oats instead of wild oats studied due to the difficulty of being reliable Obtaining and growing plants from wild oats seeds. However, it was found that the activity of a herbicide against farmed oats gives very accurate values for the activity against wild oats.

The following compounds were tested for their effectiveness as herbicides against wild oats in admixture with 5- (2- (2-butoxyethyl) ethoxymethyl) -6-propyl-1,3-benzodioxole (common name: piperonyl-buto.xide) as a synergist:

(a) 4-chloro-2-butynyl-m-chlorocarbanilate (CARBYNE; 25% emulsifiable concentrate);

(b) methyl 2-chloro-3- (4-chlorophenyl) propionate (BIDISIN; 50% emulsifiable concentrate);

(c) 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate (AVENGE);

(d) 2,4-dichlorophenyl-4- (2-methoxycarbonylethyloxy) phenyl ether (HOE 23408; 36% emulsifiable concentrate).

The products (a), (b) and (d) were used in the form of their commercially available, emulsifiable concentrates, the Product (c) was processed into a similar preparation with the following composition:

Mineral oil 100 g

Emulsifiers 60 g

Cyclohexanone 200 g

o-xylene to 1 1

The synergist was made as a 20% emulsifiable concentrate Prepared according to the recipe given for AVENGE, but without mineral oil.

The preparations were applied as mixtures produced in the storage container ("in tank mixtures") in order to achieve the to obtain desired concentrations.

709818/1061 ** ^{/ ö}

In a number of 7 cm pots with John Innes compost No. 1, 25 to 30 seeds of cultivated oats (Avena) were sown. When the plants are 1 to 1 1/2 in size Had reached leaves, a solution of the mixture to be examined was sprayed with the help of a spray device, to achieve a logarithmic dilution in 5 different doses per substance. The mixtures different proportions of the compounds were also sprayed on in 5 doses each.

Investigations were carried out 8 days after the spraying. The phytotoxicity towards the oat plants was assessed visually according to a percentage scale (in which 100 means no growth after spraying and 0 means growth as in the case of untreated comparison plants). These values were analyzed with the aid of the computer in order to calculate the dose which results in a 50% inhibition of the growth of the oat plants, abbreviated as GID ₁ -Q.

The results are given in the following table, in which the last column shows the respective dose in kg / ha for the Indicating compound against wild oats. It can be seen that the combined dose of compound against wild oats and Synergist can be calculated from these values by multiplying these values by a factor that has been obtained is from the weight ratio of the compound to the synergist,

../Tabel

709818/1061

Tabel

HerMcid against
wild oats Weight ratio
Connection: synergist GID ₅₀ (kg / ha)
for the herbicide
against wild oats
in the mixture (a)
I. 1-0
2: 1
1: 1 0.26
0.13
0.10 (b) 1-0
2: 1
1: 1 14.2
9.3
8.2 (c) 1-0
2: 1
1: 1 0.86
0.60
0.48 (d) 1-0
2: 1
1: 1 0.65
0.45
0.48

From the above results it appears that the presence of the synergist leads to a marked increase in the activity of the compound active against wild oats, in that the dose required to achieve a 50 % reduction in plant growth is always less than when the synergist is absent.

The experiments have shown that the synergist is not phytotoxic even at the doses used in the examples Exerts effect and that the selectivity of the herbicide against wild oats in no way by the presence of the synergist in the mixture is deteriorated.

../Patent claims

709818/1061

Claims (5)

Claims (?) Herbicidal agent against wild oats, containing one of the following compounds as an active ingredient: (a) 4-chloro-2-butynyl-m-chlorocarbanilate; or (b) methyl 2-chloro-3- (4-chlorophenyl) propionate; or (c) 1,2 ~ dimethyl-3,5-diphenylpyrazolium methyl sulfate; or (d) 2,4-dichlorophenyl-4- (2-methoxycarbonylethyloxy) -phenyl- ether, characterized in that it is additionally as a synergist containing a methylenedioxybenzene derivative of the general formula: (D in which Y is a hydrogen or halogen atom or an alkyl group, a straight-chain, branched or cyclic polyether group; X is a straight chain ₇ branched or cyclic polyether group, a halogen atom or a Cyano, cyanomethyl, hydroxymethyl, mercaptomethyl or an ethynyl group, a group of the formula -CH = NOR (where R is an alkylcarbonyl group), a group of the formula * 1 Ί -CH = CH-R (where R is a pyridyl group), a group of the formula-CONR ² R ³ or -CSNR ² R ³ (where R ² and R ^{3 are} each a hydrogen atom or an alkyl, alkoxycarbonylalkyl, aryl or Haloaryl group), a group of the formula -CH ₂ CH (CH ₃ ) -SO (CH ₂ J ₇ CH ₃ , a cycloalkyl group which is substituted by 1 or 2 alkoxycarbonyl groups and / or alkyl groups, one, optionally by an alkyl and / or alkoxycarbonyl group substituted cycloalkanone 709818/1061 group or one if necessary. Alkyl-substituted cycloalkenylon group or X and Y together represent one are alkylene groups optionally substituted by 1 or 2 alkoxycarbonyl groups and / or alkyl groups. 2. Means according to claim 1, characterized in that the compound of formula I the halogen atom is a chlorine, bromine and / or fluorine atom, the alkyl, cycloalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, Cycloalkanone and cycloalkenylon groups each contain up to 6 carbon atoms, the alkylene chain up to Contains 4 carbon atoms, the aryl group is a phenyl group and the polyether group is an aliphatic group Group is where the number of oxygen ether bonds ranges from 2 to 6 and which contains up to 20 carbon atoms. 3. Composition according to claim 1 or 2, characterized in that the synergist 5- (2- (2-butoxyethyl) ethoxymethyl) -6-propyl-1,3-benzodioxole is. 4. Means according to claim 1 to. 3, characterized by g e that the weight ratio of herbicide against wild oats to methylenedioxybenzene derivative in the range from 10: 1 to 1:10, preferably in the range from 5: 1 to 1: 1. 5. Means according to claim 1 to 4, characterized in that it also has a carrier and / or contains a surfactant. 709818/1061