DE1567012C - Herbicidal agent - Google Patents

Description

3 4

concentrations in the range of 3.36 to 22.4 kg / ha) without damaging or destroying the chemical with the first 5 or 10 cm of soil for harvest. Mix lesser time this application.
Amounts can be used to retard the weed wax turns used in the present invention, mixtures containing the dialkyl preventive herbicides possessing the necessary tridecylamine salts can be used as dispersions 5 properties for effective application on the in water or as water solutions with or without a field. Ideally, it should be possible to use a herbicide-compatible wetting agent which is applied to the soil surface in the germination zone from penetrating the plant and soil surfaces. Weed seeds which tend to support each other. By adding water-soluble solvent located above the zone in which the planting agents such. B. ethylene glycol, diacetone alcohol 10 takes place. The small weed seeds usually appear, methanol, ethanol, etc., and they can only be found in the top 3 cm of the earth. In the make it even more water-soluble. However, due to proper aqueous practice it is impossible to maintain a separation of the concentrates of the sparingly water soluble chemical and the plant seed by grinding the solid material in a th, therefore a herbicide should be selective and without ball milling in water with a suitable wettability 15 significant damage the planting as many training and suspending agents, such as. B. a lignin-unwanted weeds as possible to fight, sulfonate or bentonite, dilute solutions of these are quite unique and extremely speci-Methocel, etc. produce. fish properties of the chemical required because

In addition to many species of weeds, the preparations according to the invention can be found botanically. In the

the amine described as emulsion concentrates for the dilution 20 of the present invention

Manufacture in water for field applications. salts meet this requirement. Also are

These can be made resistant to decomposition by using suitable chemicals

Solvents such as B. xylene, heavy aromatic due to various factors that occur in the soil

Naphtha and isophorone are present with the addition of a suitable environment, e.g. B. Absorption by the

Produce emulsifiers, which usually contain clay components of the soil, fluctuations in pH

of various compounds with devaluations, microbiological decomposition, ultraviolet rays

appropriate distribution of the oil and water solubility, loss of volatility, etc. Depending on the dosage,

Properties and in the presence of the connection rain and soil temperature show the amine salts

are persistent. a weed killer lasting 2 to 12 months

Wettable powders can be acted upon by direct grinding. This is an advantage, as the more resistant dry compound with a mixture with digen chemicals carried off until the next season a suitable dispersant, such as. B. Atta- can be, which is undesirable. The invention pulgit, Manufacture bentonite, diatomite, etc. Preferred total herbicides show a broad mode of action Such a mixture should be in a hammer area to control weeds, which is very difficult be ground so that 99% is desired by a 35, as most additions with many Go sieve with openings of 0.044 mm. Wettable species of both grasses and broad-leaved ones Powders can also be contaminated by absorption of a weed. The invention Solutions of the compound in a solvent such as preventive herbicides are suitable for use z. B ,. Xylene or acetone on a powder or on specific crops and show a high granular clay such as attapulgite or di- 40 tolerance to all types of additions, Making atomic earth. All wettable powder- This tolerance shows up in all types of soil and preparations should use a dispersant such as B. under different environmental conditions, which a lignosulfonate and a wetting agent such as e.g. B. the reaction of a plant cultivation to a chemistry Contain alkylaryl polyether glycol. Kalie can change.

The agents according to the invention can also be used as combats with a 5 to 20% share of the fungus of the weeds after the active cultivation has appeared Use herbicidal content. The plants are used when the latter is sufficient user can be instead of an atomizer or spray-resistant. These applications can Device use a device for applying grains - especially in the time between their emergence the, and known, in the industry standard procedures 50 and the first cultivation of the crop are carried out, can be used for the production of granular preparations but treatments can also be used later. men, z. B. after the last possible cultivation

As already mentioned, the preparations are suitable for preventing weed growth

especially for preventive use at harvest time. ;.

different crops for weed control. 55 Certain preparations according to the invention can be

In this weed control process with one to use in support of the harvest, taking them

The chemical becomes herbicide some time before the green leaves of sensitive crops.

The plants emerge on the ground. neither dry out nor throw away and

The application can expediently at the same time - also dry out the weeds present,

Carry out early sowing and close 60 to machine harvesting with a combine

usually the use of a spray attachment in the case of seeds or with a picking machine

to the planter, which the diluted chemical in a cultivation such. B. To facilitate cotton,

kälie immediately after the soil has been covered. Certain preparations can be used in higher doses

with the seed on the surface of the earth. You use and then effect a sterilization of the

can only one strip of the seed row with the 65: soil against any plant growth. The season-

Hejcicide treat, or you can do the entire i proper control of weeds in areas like

Treat the area on a broad basis. At the j ζ. B. industrial centers and roadsides etc. can

Using a rotocultivator, you can remove the vegetation that is unwanted in this way.

By using solutions, emulsification concentrates or wettable powder preparations the surface of beds in the greenhouse were the dialkyltridecylamine salts of the invention Endothal for its preventive weed control properties before being treated with beets, peas, soybeans, Flax and cotton, as well as with weed seeds of Amarathus sp. (red root), Chenopodium album, Portulaca sp. (Protulak), Setaria sp. (Foxtail) and Digitaria sp. (Crab grass) etc. planted. the The preparation was used immediately after the crops and weeds were planted. the Test beds were then placed in the greenhouse under suitable conditions, and after three to A count of emerging crops and weeds was made for four weeks. the Flower beds were usually kept for a second count in order to have secondary effects on the Observe growing plants and further evaluate the rest of the weed control.

ίο The following tables show the results of the Preventive tests and show the excellent effectiveness of dimethyltridecylamine salts,

Table I: Preventive Attempt
Part 1 - Percentage of weed destruction

Active agent

Amount used, moles / ha foxtail

Crab grass

Lambsquarter

Amaranthus

Purslane

Endothal disodium salt

Neutral. Dimethyltridecylamine salt of Endothal ...; ..; ...;

Mono-dimethyltridecylamine salt from Endothal

Neutral. Soy amine salt from

Endothal *)

Neutral. Dimethyl soy amine salt

from Endothal *) ....;

Neutral. Oleylamine salt of

Endothal

Neutral. Dimethyloleylamine salt

from Endothal

Neutral. Dimethyl cocosamine salt

by Endothal **)

60.4 30.2

30.2 15.1

30.2 15.1

30.2 30.2 30.2 30.2

30.2 15.1

0
10

100
100

100
100

15th
0
0
0

50
0

40 20

100 85

90 50

65 0

15 0

0 0

60 20

100 '96

100 100

0 60 80

100 60

80

100 100

100 100

20th

65

15th

80

45

*) Soybean amine has an average chain length distribution of 84% C-18 and 16% C-16.
**) Coconut amine has an average chain length distribution of 49% C-li2.17% C-IA, 9% C-16, 10% C-18, remainder C-8 and C-IO.

part 2 -— Percentage growth in cultivation Sugar ^
beets cotton peas soy
beans flax Used
crowd
Moles / ha 87
75
70
75 70
56
70
70 20th
100
60
80 100
100
90
100 20th
55
85
80 Neutral. Dimethyltridecylamine
Salt of Endothal
Mono-dimethyltridecylamine salt
from Endothal 30.2
15.1
30.2
15.1

Also, evaluations were made according to the emergence of the crops by application on beds that contain weeds and crops 6 to 8 weeks old. The following Table II shows the effects of application after the emergence of various weeds and crops.

Tables: product Contact attempt (after the plants emerge) Fox
tail Crab grass Lamb's
quarter sugar
beets tree
wool soy
beans flax Neutral. Endothal salt of
Dimethyltridecylamine
Mono-dimethyitridecylamine
Salt from Endothal Meiige / ha 80
80 50
50 40
40 5
10 60
60 80
40 ioö
100 2.8 kg
2.8 kg

As can be seen from the tables above, weed control is with the dimethyltridecylamine salts from Endothal exceptionally well and surprisingly the disodium salt from Endothal or other long chain amine salts from Endothal. In addition, from Part 2 of Table I shows that the growth of the crops treated with the total herbicides according to the invention is quite good is high and thus the good tolerance of the dimethyltridecylamine salts of endoxohexahydrophthalic acid for the attachments shows. Table II shows the effective weed control that can be achieved with the amine salts according to the invention after surfacing

the crops and the effect on the crops. Instead of using of the dimethyltridecylamine salts one can also use the endoxohexahydrophthalic acids according to the invention Salts of diethyltridecylamine, di-isopropyltridecylamine, Use di-tert-butyltridecylamine with essentially the same results.

In addition to their usefulness as preventive and contact herbicides, the compositions of the invention can also be used also to control other types of plant growth, e.g. B. of aquatic weeds, use. They also have the effect of destroying unwanted soil fungi.

209546/518

Claims (2)

1, .2 Claim · of ^{the compound} S- ^It has now been found that with Use of the dimethyltridecylamine salt of Herbicidal agent, labeled "endothalic acid" as a field weed killer, by a content of a Ν, Ν-dialkyl especially as a preventive herbicide, its active tridecylamine salt the endoxohexahydrophthalic acid, 5 efficacy exceeds that of where the Ν, Ν-dialkyltridecylamine expects the formula the herbicidal acid content. It appears, that the dimethyltridecylammonium cation to the ¹ X herbicidal effect of the anion portion of the molecule -N — CH ₂ - Ci ₂ Hi ₅ contributes. As a result, allows use π / ίο the dialkyltridecylamine salts of "endothalic acid" the ² . . Obtaining excellent preventive Beaufweist, low in the R ₁ and R _{2 are} alkyl groups combating -at different pose, and the group of a large number - ■ C ₁₂ Hi ₅ ^{e 'ne} highly undesirable plants in acceptably low branched chain has: concentrations and at low cost . 15 Since the acid present in the agents according to the invention, 3,6-endoxohexahydrophthalic acid The invention relates to a herbicidal agent (endothalic acid), which has more than one carboxylic acid group characterized by a content of one N, N-di-, the dialkyltridecylamine salt can be used as the monoalkyltridecylamine salt of the endoxohexahydrophthalic, salt or as a neutral di-salt,
acid, the Ν, Ν-dialkyltridecylamine of the formula "20 The amine salts of the present invention can be very easily mel by adding stoichiometric R ₁ . Amounts of dimethyltridecylamine to 3,6-endoxohexa- \ ν, £ jr CH hydrophthalic acid in the presence or absence of a / 2 12 i;> mutual solvent. At a R2 25 preferred method, you only need stoichio- metric amounts of dimethyltridecylamine and has, in which R ₁ and R ₂ lower alkyl groups 3,6-endoxohexahydrophthalic acid with or without representation and the group —C ₁₂ Hi ₅ a strong,>: ■ dispersing agent (such as ethylene glycol) in water to branch Chain has. give and mix until a homogeneous dispersion As is well known, numerous amines act and their 30 or solution of the salt is achieved. Instead of one Apply salts to living plants. As now found aqueous system, you can use solvents such. B. is the effect of Ν, Ν-dialkyltridecyl aromatic hydrocarbons (e.g. benzene, toluene, amine salts of endoxohexahydrophthalic acid. on xylene), esters (e.g. ethyl acetate), alcohols (e.g. Plants use surprisingly strong, especially if ethanol) and the like., As a medium, the this .specific group of amines as a preventive reaction participant in the heated solution legend "Herbicides are used. Medium mixed and as a solid precipitate when The alkyltridecylamines will preferably be obtained from cooling. Another possibility of the Tridecyl- obtainable by the oxo process is to obtain the reactants with ambient alcohol, namely the oxo-alcohol is mixed at temperatures or slightly elevated temperatures in the presence of heat and pressure in the presence of 40 without a liquid medium apart from the dimethyltri-alumina as a catalyst with lower dialkylamine decylamine itself,
(e.g. diethylamine) 'implemented. After the USA .-- '■ B eis ρ ie 1 1 Patent 2,043,965 gives dialkyltridecyl- amine. The structure of the amine agrees with 1135g of 3,6-endoxohexahydrophthalic acid (Endothal- the oxo reaction products, as the; long-acid 45 ° / ₀ active ingredient), 1167g dimethyl-chain alkyl group. via a primary carbon .tridecylamine (95 ° / ₀ active ingredient) and 1512 g atom is bonded to the nitrogen atom (ie water are mixed and stirred until a homo-CH ₂ - N), while it is otherwise a branched solution. The product obtained is a chain residue. This structure of the amine is on _; aqueous solution of the mono-dimethyltridecylamine attributed to the fact that the oxo process 5 ° salt of Endothal with a concentration of always to a product with a larger proportion ■ 530 g / l. leads from branched connections. Oxo-Tridecyl- Example 2 alcohol is therefore a polybranched primary ali- phatic alcohol which g by the Oxo process 908 Endothalsäure (80 ° / ₀ active ingredient) is made from tetrapropylene and when converted 55 1861g dimethyltridecylamine (95 ° / ς active constituent to the amine with, for example, dimethylamine part), 568 g of water and 341 g of ethylene glycol (as a polybranched tertiary amine with the for- dispersant) are mixed until a homogeneous one mel solution is achieved. This product is the neutral one C ^ H ₂₅ - CH ₂ -N- (CH ₃ ), dimethyltridecylamine salt of Endothal (i.e. the 60 diamine salt), and the aqueous mixture contains that results. In the present invention, the salt becomes salt at a concentration of 660 g / l.
des Ν, Ν-dimethyltridecylamine preferred. The amine salts according to the invention are also It is known that herbicidal acids in the form of fairly effective herbicides; they are suitable ins amine salts can be applied. So far special as preventive herbicides for control rather large quantities of these salts became weeds and undesirable for extermination and the vegetation obtained in these applications. You can at exceptionally low Herbicidal effects correspond to their size concentrations between 3.36 and 112 kg / ha regulation according to the active herbicidal acidity (preferably the concentrations are