DE3330546A1 - HERBICIDES - Google Patents

Abstract

1 The invention relates to herbicides containing a) N- (ethyl) -N- (2-methallyl) -2,6-di- (nitro) -4- (trifluoromethyl) -aniin of the formula as active ingredient, optionally together with one or more usual carrier (s), solvent (s), diluent (s), auxiliary (s) and / or other additive (s), which in a mixture with the N- (ethyl) -N- (2-methallyl) -2,6-die- (nitro) -4- (trifluoromethyl) aniline of the formula [component, a)].

Description

In Hungary, autumn wheat is grown on an area of around 1 200 000 hectares and around 95% of it is chemical weed control. According to current practice, the treatment is carried out in the 3 to 5-leaf stage of autumn wheat or afterwards in the period between perennials and weeds, i.e. weed control is carried out in spring in post-emergent treatment. Lately, pre-emergent and post-emergent treatment in autumn have also become more widespread, which can be extremely important in terms of increasing yields. In practice, weed control carried out in spring has proven its worth because the herbicides available use hormonal agents such as 4- (chlorine) -2- (methyl) -phenoxyacetic acid {MCPA},
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- [4- (Chlor) -2- (methyl) -phenoxy] -propionic acid {MCPP}, 2,4-dichlorophenoxyacetic acid {2,4-D}, 2,4-DP or 4- [2´, 4´- Di- (chloro) -phenoxy] -butyric acid {2,4-DB}, 3,6-di- (chloro) -2- (methoxy) -benzoic acid {dicamba} and 9- (hydroxy) -fluorenecarboxylic acid- (9) {Flurenol}, as well as contact preparations such as 3- (isopropyl) -1H-benzo-2,1,3-thiadiazin-4-one-2,2-dioxide {bentazon} and 3,5-di- (bromine) -4 - (hydroxy) -benzaldehyde- [2´, 4´-di- (nitro) -phenyl] -oxime {bromofenoxime} exercise their optimal selectivity and effectiveness between the time of perennials and shot. It is known that the above herbicides are only effective against broad-leaved weed plants, but are even ineffective against some broad-leaved weed plants. If the herbicides are used for several years, resistant weed plants develop, which also reproduce. The number and amount of

Species Centaurea cyanus L. (cornflower), Cirsium arvense L. Scop. (Thistle), Consolida spp., Sinapis arvensis L. (mustard), Papaver rhoeas L. (poppy) and Raphanus raphanistrum L. have decreased and the following weed plants with T [deep] 1- and T have replaced these plants [deep] 2 life forms:

Life form T [deep] 1

Capsella bursa-pastoris L. medic Common shepherd's purse

Lamium amplexicaule L. Dead nettle embracing the stem

Lamium purpureum L. Red dead nettle

Myosotis arvensis L. Hill Forget-me-nots

Spergula arvensis L. Common sparrow

Stellaria media L. Cyr. Chickweed

Veronica hederaefolia L. Ivy-leaved speedwell

Veronica persica Poir. Persian Speedwell

Veronica polita fr.

Life form T [deep] 2

Adonis aestivalis Summer Adonis

Anthemis arvensis L. Field chamomile

Anthemis cotula L. Smelly dog chamomile

Galium aparine L. Burdock weed

Lithospermum arvense L. Arable stone seeds

Matriciaria chamomilla L. Real chamomile

Thlaspi arvense L. Field pennywort

Viola arvensis Murr. Sand pansy

In recent years, the eradication of the monocot weed plants that have appeared in large areas of Hungary has caused great problems. Of these weed plants are the Alopecurus myosuroides Huds, which also germinate in autumn. (Black foxtail) and Apera spica-venti L.P.B. (Windhalm) mentioned. Attempts were made to control the weed plants in autumn and early spring with pendimetalin, 3- (3'-chloro-p'-tolyl) -1,1-dimethylurea [chlorotoluron] and isoproturon containing agents. Although these herbicides can be used against the above monocot weed plants with relatively good efficiency, they are effective against several dicotyledon species such as Capsela bursa-pastoris L. Medic. (common shepherd's purse). Viola arvensis Murr. (Sand pansy) and Veronica hederaefolia L. (ivy-leaved speedwell) are not sufficiently effective. It is known that autumn wheat, similar to other crops, is most sensitive to weed damage at the beginning of growth; the elimination of weed competition in the early stages (juvenile weed competition) therefore plays an essential role in the growth of the crop. It is also known that in the case of wheat sown in the optimal sowing period at the end of September or beginning of October, the weed plants with T [deep] 1 and T [deep] 2 life forms open up in autumn. If these weed plants are destroyed in autumn or at the end of winter or at the beginning of spring, they cannot prevent the growth of wheat and perennials and an increase in yield can therefore be expected.

The following emerges from the textbook "The Pesticide Manual" (Sixth Edition, London, 1979, C. R. Worthing). According to page 240 of this book, N-Ethyl-N- (2-methallyl) -2,6-di- (nitro) -4- (trifluoromethyl) -aniline [Etalfluralin] of the formula

I.

can be used for weed control on cotton, beans or soy by incorporating into the soil at rates of application of 1.0 to 1.25 kg / ha. On page 502 of this book it is proposed that 2- (tert-butylamino) -4- (chloro) -6- (ethylamino) -1,3,5-triazine [terbutylazine] of the formula IIa

to be used as a selective herbicide in application rates of 1.2 to 1.8 kg / ha in maize, grape and lemon crops. According to page 503 of said book, 2- (tert-butylamino) -4- (methylthio) -6- (ethylamino) -1,3,5-triazine [Terbutryn] of the formula

IIb

at application rates of 1 to 2 kg / ha for autumn wheat, sugar cane and beans as a pre-emergent herbicide or for maize as a post-emergent herbicide. According to page 501 of said book, 2- (tert-butylamino) -4- (methoxy) -6- (ethylamino) -1,3,5-triazine [terbumetone] of the formula IIc

can be used in application rates of 3 to 10 kg / ha in lemon, apple and grape plantations as a post-emergent herbicide.

It is well known that the above 4 compounds have a narrow spectrum of activity per se. It goes from the state of the

Technology shows that only 2- (tert-butylamino) -4- (methylthio) -6- (äthylamino) -1,3,5-triezine [terbutryn] is suitable for weed control in advance application in autumn wheat. In practice, however, this agent has not found widespread use either. For the other 3 compounds, the technical literature, in particular with regard to the preliminary application, does not even provide any information at all. It was also not known that the N-ethyl-N- (2-methallyl) -2,6-di- (nitro) -4- (trifluoromethyl) -aniline [etalfluralin] in wheat without being incorporated into the soil before emergence the weed plants or up to the 2 to 3-leaf stage can be used with success.

The invention is based on the object of providing superior herbicides which can be used both in autumn and in spring and, due to their broad spectrum of activity, enable the control of monocotyledonous and dicotyledonous weed plants without exerting a toxic effect on the crop plants such as autumn wheat , to accomplish.

The above has surprisingly been achieved by the invention.

It has been surprisingly found that herbicides, the combinations of which were previously completely unknown, are excellently suited for achieving the above.

First of all, it was found that the compounds in question exert a selective effect up to the 2 to 3-leaf stage of wheat when applied first. Thereafter, the synergetic effect in those weed plants which the individual compounds alone was known

Well tolerated, definitely. It was surprisingly found that all combinations of N-ethyl-N- (2-methallyl) -2,6-di- (nitro) -4- (trifluoromethyl) -anilines [Etalfluralines] of the formula I with the compounds 2- ( tert-butylamino) -4- (chloro) -6- (ethylamino) -1,3,5-triazine [terbutylazine] of the formula IIa, 2- (tert-butylamino) -4- (methylthio) -6- ( ethyl-amino) -1,3,5-triazine [terbutryn] of the formula IIb and 2- (tert-butyl-amino) -4- (methoxy) -6- (ethylamino) -1,3,5-triazine [ Terbumetone] of the formula IIc exert a significant synergetic additional effect in certain proportions. The proportions showing a synergetic effect were also determined.

The invention therefore relates to herbicides containing

a) N- (ethyl) -N- (2-methallyl) -2,6-di- (nitro) -4- (trifluoromethyl) aniline of the formula I.

as active ingredient, optionally together with 1 or more customary carrier (s), solvent (s), diluent (s), auxiliary (s) and / or other additive (s), which are characterized in that they are mixed with the N - (Ethyl) -N- (2-methallyl) -2,6-di- (nitro) -4- (trifluoro-methyl) -aniline of the formula I (component a)] b) 1 or more 4-substituted [s ] 2- (tert-Butylamino) -6- (ethylamino) -1-3-5-triazine (s) of the general formula II

wherein

X stands for chlorine, a methylthio radical or a methoxy radical,

as further active ingredient (s)

included, the weight ratio of a) to b) being 19: 1 to 1: 4.

The mixture of a) and b) is advantageously present in them in amounts of 0.1 to 85.0% by weight.

The weight ratio of a) to b) is preferably from 4: 1 to 1: 1.

The herbicides according to the invention can be in the form of aqueous solutions, optionally mineral oil-containing solutions in organic solvents, concentrates emulsifiable in water, powders or powder mixtures which form a stable suspension with water, aqueous or oily emulsions, aqueous suspension concentrates, aqueous pastes and granules. Natural or synthetic materials of organic or inorganic origin, for example finely ground mineral or vegetable substances, plastics, silicates and / or magnesium oxide, can be used as solid carriers. Suitable liquid diluents are advantageously water or liquid aliphatic aromatic hydrocarbons or derivatives thereof, for example aliphatic or aromatic alcohols, ketones, esters or halogen derivatives or mixtures of these. Wetting agents and / or dispersants, for example non-ionic and / or anionic surfactants and / or lignosulfonic acid derivatives and / or adhesives or agents that increase adhesion and / or agents that reduce evaporation and / or stabilizers can be used as auxiliaries and other additives . The concentrates with a high active ingredient content are diluted to the desired concentration before being used in agriculture and then applied to the field with the help of suitable equipment.

A great advantage of the herbicides according to the invention is that their use solves a serious problem in agriculture, i.e. the effective control of a wide range of monocotyledonous and dicotyledonous weed plants which damage the crop plants, in particular autumn wheat, without adversely affecting the crop plants. Furthermore, the herbicides according to the invention accelerate weed control, they can also be used with preliminary treatment and create very favorable conditions for the growth of the crop plants, in particular that of autumn wheat, and all of this clearly results in an increase in yield. Another advantage is that the invention of the plant protection product treasure by new, very effective and extensively expanded reversible herbicides enriched.

The herbicides according to the invention can be used in crops of arable plants, in particular in the case of autumn wheat, for controlling weeds in pre-run and post-run applications.

The invention is explained in more detail with reference to the following examples.

example 1

A series of solutions which can be immediately sprayed without dilution with water were prepared using a mixture of N-methyl-small alpha-pyrrolidone and ethanol in a weight ratio of 30:70 as solvent, a polyoxyethylene sorbitan monolaurate as surface-active agent and N-ethyl-N- (2nd -methallyl) -2,6-di- (nitro) -4- (trifluoromethyl) -aniline [etalfluralin] of the formula I and 2- (tert-butylamino) -4- (chloro) -6- (ethylamino) -1 , 3,5-triazine [terbutylazine] of the formula II, in which X stands for chlorine, that is of the formula IIa, as active ingredients. The proportions of the two ingredients in the agents were 0.4: 1.6, 0.7: 1.3, 1.0: 1.0, 1.3: 0.7, 1.6: 0.4 and 1, respectively , 9: 0.1. The total active ingredient content was 20% by weight. Using the above solvents and surface-active agents, series of solutions containing only 1 of the two above active ingredients were also prepared, in such a way that the individual solutions had the same amount of the active ingredient as the amount of the active ingredient in question in the above 2 Components of existing funds was included. The effectiveness of the solutions thus obtained was tested in a glass house on Triticum aestivum ssp. vulgare (autumn wheat) as a cultivated plant and at

Capsella bursa-pastoris (common shepherd's purse), Viola Arvensis (sand pansy), Veronica hederaefolia (ivy-leaved speedwell), Apera spica-venti (wind stalk) and Alopecurus myosuroides (foxtail) as weed plants with T [deep] 2 1- and T [deep] 2 -Life forms determined. After the seeds had been sown and covered, the surface of the soil was sprayed with the agents in the application rates given in Table 1 below. The extermination symptoms were observed 14 days after the treatment. The results obtained are shown in Table 1 below. The synergetic effect was calculated on the basis of the following table 1 with the aid of the procedure of Colby (Weeds, January 1967, pages 20 to 22). The results obtained are shown in Table 2 below.

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From the above Table 2 it can be seen that with the active ingredient combination according to the invention with the active ingredient quantity ratios used, a certain synergism occurred in each case. The best results were obtained on all the weed plants examined using the active ingredient combination N-ethyl-N- (2-methallyl) -2,6-di- (nitro) -4- (trifluoromethyl) -aniline [etalfluralin] + 2- (tert. -Butylamino) -4- (chlorine) -6- (äthylamino) -1,3,5-triazine [terbutylazine] with proportions of the former to the latter of 1: 1 {D [deep] 2 + A [deep] 3}, 1.3: 0.7 {D [deep] 3 + A [deep] 2} and 1.6: 0.4 {D [deep] 4 + A [deep] 1}.

Example 2

A series of powder mixtures forming stable and sprayable suspensions with water using kaolin and silicon dioxide (silicic acid anhydride) as a carrier, sodium lignosulfonate and a fatty alcohol sulfonate as auxiliaries and N-ethyl-N- (2-methallyl) -2,6-di- (nitro) -4- (trifluoromethyl) -aniline [etalfluralin of the formula I and 2- (tert-butylamino) -4- (methylthio) -6- (ethylamino) -1,3,5-triazine [terbutryn] of the formula II, in which X stands for a methylthio radical, that is of the formula IIb, as active ingredients. The proportions of the two ingredients in the powder mixtures were 0.4: 1.6, 0.7: 1.3, 1.0: 1.0, 1.3: 0.7, 1.6: 0.4 and 1, respectively , 9: 0.1. The total active ingredient content was 50% by weight. Using the above carriers and auxiliaries, series of powder mixtures each containing only 1 of the two above active ingredients were also prepared, in such a way that these powder mixtures contain the same amount of the active ingredient as the amount of the active ingredient in question in the two ingredients Funds was included. the end The powder mixtures were prepared by diluting with water spray. The spray test described in Example 1 was carried out using the application rates given in Table 3 below. The results obtained are shown in Table 3 below. The data of the synergetic or antagonistic effect calculated on the basis of the following Table 3 with the aid of Colby's procedure (if the latter is present, a minus sign is in front of the relevant number) are compiled in Table 4 below.

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From the above table 4 it can be seen that with the active ingredient combination according to the invention in almost every case - and with regard to the weed plants Viola arvensis (sand pansy), Veronica hederaefolia (ivy-leaved speedwell) and Apera spica-venti (wind stalk) pronounced in every case - a certain synergism occurred. The best results were obtained on all the weed plants examined using the active ingredient combination N-ethyl-N- (2-methallyl) -2,6-di- (nitro) -4- (trifluoromethyl) -aniline [etalfluralin] + 2- (tert. -Butylamino) -4- (methylthio) -6- (äthylamino) -1,3,5-triazine [Terbutryn] with proportions of the former to the latter of 1: 1 {D [deep] 2 + B [deep] 3}, 1.3: 0.7 {D [deep] 3 + B [deep] 2} and 1.6: 0.4 {D [deep] 4 + B [deep] 1}.

Example 3

A series of concentrates emulsifiable in water was made using cyclohexanone, butyl acetate and isobutanol in a volume ratio of 3: 1: 1 as solvents, an alkylarylsulfonate and a polyethylene alkylphenol in a weight ratio of 2: 3 as surface-active agents and N-ethyl-N- ( 2-methallyl) -2,6-di- (nitro) -4- (trifluoromethyl) -aniline [Etalfluralin] of the formula I and 2- (tert-butylamino) -4- (methoxy) -6- (ethylamino) - 1,3,5-triazine [terbumetone] of the formula II, in which X stands for a methoxy radical, that is of the formula IIc, as active ingredients. The proportions of the two ingredients in the concentrates were 0.4: 1.6, 0.7: 1.3, 1.0: 1.0, 1.3: 0.7, 1.6: 0.4 and 1, respectively , 9: 0.1. The total active ingredient content was 40% by weight. Using the above carriers and excipients, series of concentrates each containing only 1 of the two above active ingredients were also prepared, in such a way that these concentrates contain the same amount of the active ingredient in question, what the amount of the active ingredient in question was in the concentrates consisting of the two ingredients mentioned. Sprays were prepared from the concentrates by diluting them with water. The spray test described in Example 1 was carried out using the application rates given in Table 5 below. The results obtained are shown in Table 5 below. The data of the synergetic or antagonistic effect calculated on the basis of the following Table 5 with the aid of Colby's procedure (if the latter is present, a minus sign is in front of the relevant number) are compiled in Table 6 below.

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It can be seen from Table 6 above that, with one exception, some synergism occurred in each case. The best synergetic results were obtained on all the weed plants examined using the active ingredient combination N-ethyl-N- (2-methallyl) -2,6-di- (nitro) -4- (trifluoromethyl) aniline [etalfluralin] + 2- (tert .-Butylamino) -4- (methoxy) -6- (äthylamino) -1,3,5-triazine [terbumetone] with proportions of the former to the latter of 1: 1 {D [deep] 2 + C [deep] 3} , 1.3: 0.7 {D [deep] 3 + C [deep] 2} and 1.6: 0.4 {D [deep] 4 + C [deep] 1}.

Claims (3)

1.) Herbicides containing a) N- (ethyl) -N- (2-methylallyl) -2,6-di- (nitro) -4- (trifluoromethyl) aniline of the formula (I) as active ingredient, optionally together with 1 or more customary carrier (s), solvent (s), diluent (s), auxiliary (s) and / or other additive (s), characterized in that they are mixed with the N- ( Ethyl) -N- (2-methylallyl) -2,6-di- (nitro) -4- (trifluoromethyl) aniline of the formula I [component a)] b) 1 or more 4-substituted [s] 2- (tert-butylamino) -6- (ethylamino) -1,3,5-triazine (s) of the general formula II wherein X stands for chlorine, a methylthio radical or a methoxy radical, as further active ingredient (s) included, the weight ratio of a) to b) being 19: 1 to 1: 4. 2.) Herbicides according to claim 1, characterized in that the mixture from a) to b) is present in them in amounts of 0.1 to 85.0% by weight. 3.) Herbicides according to claim 1 or 2, characterized in that the weight ratio of a) and b) is 4: 1 and 1: 1.