DD230757A1 - USE OF CHLORINE S-TRIAZINES AS SELECTIVE AGENTS AGAINST UNKRAEU PV AND SCHADGRAESER - Google Patents

Abstract

The invention relates to the use of chloro-cyclopentyl- or cyclohexylamine-s-triazines for the treatment of crops for the destruction of weeds and Schadgraesern. The aim of the invention is the provision of new compounds with improved herbicidal activity and / or better compatibility for the crops. According to the invention, compounds from the group of the chloro-cyclopentyl- or cyclohexylamine-s-triazines of the general formula I, in suitable administration form, in amounts of from 0.05 to 10 kg / ha, preferably from 0.5 to 2.5 kg / ha used. In the formula, for example: R1 is H, a straight- or branched-chain alkyl radical u. R2 and R3 are a radical from the group of R1 and R2; a; R is a radical from the group of the alkyls or alkoxides u. a, A-CH2, -CH2-CH2 or -CHCH-, B-CH2-, -CH2-CH2- or -CHCH-, n is 0 or 1, 2, 3, 4, 5 or 6m 0 or 1 , 2, 3, 4, 5 or 6p 0 or 1q 0 or 1.

Description

W A01 H / 247 351/4 61 853 18 20.6.83

Use of chloro-s-triazines as selective agents against weeds

Field of application of the invention

The invention relates to the use of chloro-s-triazines which are substituted with one or two Ocyclohexylamino groups having at least 3 monovalent substituents or with cyclopentylamino groups, as selective agents against weeds and grass weeds. The chloro-striazines according to the invention are used in agriculture.

Characteristic of the known technical solutions

S-triazines were first reported as fungicides by the Ethyl Corp. New York, used (DS-PS 965 608, US Prior. 31.08.1951).

The recommended compounds contain one (to two) chlorine atoms in the 2- (and 4-) position and - as the amine in the 6- and 4-position - optionally substituted - anilines or naphthylamines,

Greater success had been introduced in 1954 by the company Geigy simazine (= 2-chloro-4,6 to ethylamino-1,3> 5-triazine) (CH-PS 329 277 and 342 784 and DE-AS 1 011 904th ).

Simazine is effective against a large number of weeds and grasshoppers ₅ , but it can also damage crops, especially in the case of larger concentrations. (Striking is only the

Selectivity to maize).

Later, more s-triazines came on the market. As standard products are here only

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Atrazine , which is 2-chloro-4-ethylamijao-6-isopropylain.ino-1,3 »5-

triazine (DS-IS 1 011 904) and the

Terbutryn , which is 2-methylthio-4-ethylamino-6-tert-butyl-amino-

1,3,5-triazine (DE-AS 1 011 904, GH-PS 337 019, DE-A3 1 179 941 and 1 186 070 and 1 219 726).

The cyclohexyl group as an amine substituent was first claimed in 1962 by the HALCO Chemical Company in a herbicidal s-triazine (US Pat. No. 3,194,646), but without mentioning examples thereof. Correspondingly, the preparation of cyclohexylamine-containing triazines was also reported by Ciba-Geigy -AG 1965 under patent protection (Dl-AS 1 695 117).

Cyclohexyl-containing chloro-s-triazines have been extensively studied for their herbicidal activity by Nippon Kayaku K.K. (JA-OS 72-23436, Examples 1 to 11).

Later, this company also filed 2-chloro-4-methylcyclohexylaminos-triazines as algicidal compounds and thus offered a method for containing cohrines. (JA-OS 74-25135, according to Chem. Abstr. 81 (1974) 115,898).

Chloro-cycloalkylamino-triazines having 3 to 6 C atoms in the ring and the characteristic group -Z (CH ₂ ) J _n -Ni ^ t® ^ ^{z =} "~ °" ~ or -NH-, m = 2 or 3 i ^ and R = CH ^ or C ₂ H ^) were recommended in the textile industry by TEIJIN (JA-OS 7 409 094, according to Chem. Abstr. 81 (1974) 92 907).

To increase the root yield and the sugar content of sugar beets, Urad predsednictva Slovfnskej akademie vied in Bratislava, inter alia, proposes the use of chlorocycloalkyl-

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amino-s-triazines having 3 to 6 carbon atoms in the King before (DE-OS 2,833,582). However, as an example of a cycloalkyl group as the triazine substituent, only a cyclohexylaminos-triazine having a Metb.ylth.iogru.ppe is mentioned (I.e. page 26, Example 44).

A process for the preparation of such compounds is also disclosed by Giba Geigy in US Pat. No. 4,186,265, without, however, mentioning examples of the C 1 -Gg -cycloalkyl derivatives.

The disadvantage of the previously known chloro-s-triazines was generally their general effect, d. h »also against crops. After all, quite specific selectivities had occurred with individual s-triazine derivatives (see above those of simazine in maize or of atrazine in corn, sugar cane or pineapple or of terbutryn in winter wheat, but there are no such herbicides present in oats, barley, wheat , Ice, haps, etc. cause no damage.

Object of the invention

The aim of the invention is to provide compounds which are more effective than the already known herbicides in the destruction of the various weeds and grass weeds and / or better tolerated by the crops.

Presentation of the Invention

The invention has for its object to find substance group of compounds with the desired properties.

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A surprisingly high selectivity towards such crops could be observed according to the invention in Ohlor-s-triazines having one or two, optionally substituted, Cyclopentylaminogruppen or Cyclohexylaminogruppen with at least three monovalent substituents in 4 · (and 6) -position of the triazine ring.

Similar effects were shown by the corresponding derivatives with a CH ₂ group between the Hing and the amine nitrogen, as well as those with substituted cyclohexenamines.

BrfindungsgemäJB are therefore chloro-cyclopentyl- or cyclohexylamine-s-triazines of the general formula

Cl

Έ N,

in the

R ^ is a straight or branched chain alkyl, alkoxy. Alkoxyalkyl or alkylol Hest or - preferably - a

Η atom, R ₀ a best of the group of IL or a

-K

) (CH ₂ ) _q -test,

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R- an Eest from the group of E ^, preferably an H atom, and

H is a radical from the group of alkyls or alkoxides having one to three C atoms or hydroxyl or - to some extent as a derivative of 2 OH groups on the same carbon atom - the oxo • group and

A s -CH ₂ -, -CH ₂ - CH ₂ - or -CH a CH-, B s -CH ₂ -, -CH ₂ - CH ₂ - or -CH = CH-, η for A = -CH ₂ - each O or 1, 2, 3, 4, 5 or 6 or for A φ. -CH ₂ - each 3 t 4 »5 or 6 and m is each O or 1, 2, 3» 4, 5 or 6, and ρ = either O or 1 and q = either O or 1 and wherein of the substituents R, - to R-, at least one must be a Η-atom, and wherein the η or m substituents R may be the same or different on the saturated or given also having a double bond CycloalkyIringen, in a suitable administration form for the selective treatment of crops with broad spectrum of action on weeds and grass weeds

used before and / or after emergence of the seed.

The chains, which are formed by R ^, R ₂ or R ^, should have no consideration of the Η-atoms and regardless of the degree of branching - not more than 15 C or O atoms.

When counting the substituents R, an oxo group calculates twice (a -CH ₂ -NH group, however, does not at all, because this is taken into account by the index ρ or q = 1).

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The compounds according to the formula I are herbicides which have both in the pre- and postemergence process (Tables 3 to 5) ^e i & wide selectivity spectrum compared to numerous crops and a very good activity against grass weeds and dicotyledonous weeds.

The present compounds are preemergence and / or casserole methods selectively in soybean (17 ^ä ), cotton (4), rice (15) »maize (14), winter rape (25), barley (8) and wheat (22).

The compounds of the invention have a broad spectrum of activity against grass weeds such. B. field foxtail (1), Windhalm (24) and flying oats (6). An egg of dicotyledonous weeds is also detected, e.g. B. Chickweed (20) Klettenlabkraut (13), Chamomile (11, including Anthemis species), White Goosefoot (21), Ackersenf '(2), Dead Nettle (18), Amaranth (3), seedwort flower (16), poppy ( 12), Knotweed (5) and Frenchweed (7) ·

The starting amount may vary from 0.062.5 to 10 kg / ha, preferably from 0.5 to 2.5 kg / ha. In general, however, even 0.25 kg / ha suffice for a satisfactory effect of the pure substances. Of course, the quantities are understood to refer to the pure active ingredient per ha «

Despite the broad spectrum of activity in the cultures mentioned above, visible damage to the crop was practically not observed.

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is Botanical Kamen cf. Table 1, page 7.

(Arrangement in the list, the alphabet of the German names.The number behind the German name of the present enumeration on this page facilitates the discovery of the respective plant names).

Table 1 German name Latin name Foxtail = Alopecurus myösuroides Botanical names of the test plants charlock = Sinapsis alba Amaranth = Amaranthus retroflesus 1. cotton = Gossypium hirsutum Second Flea knotweed = Polygonum persicaria Third oats = Avena fatua 4th French herb = Galinsoga parviflora 5 · barley = Hordeum vulgar 6th oats = Avena sativa 7th barnyardgrass - Echinocloa crus-galli B. chamomile = Matricaria maritima 9th poppy = Papaver rhoe as 10th cleavers = Galium aparine 11th Corn = Zea mays 12th eeis = Oryza sativa 13th Seed worm flower = Chrysanthemum segetum 14th soy = Glycine max 15th dead nettle =. Lamium purpureum 16th tomato = Lycopersicum esculentum 17th chickweed = Stellaria media 18th White goosefoot = Ohenopodium alba 19th 20th 21st

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22 · wheat = Triticum aestivum

23. Wioke = Vicia angustifolia

24 · Windhalm = Apera spie a-vent i

25, winter rape = Brassioa napa

26 · Sugarbeet = Beta vulgaris

The novel compounds of formula I can be prepared by methods known per se, by cyanuric chloride - preferably in a solvent or solvent mixture, ζ. Example in acetone, acetone / water, dioxane, dioxane / water, tetrahydrofuran or in Birnethylformamid - denjsntsprechenden with amines in the respectively appropriate conditions (temperature, usually between -30 ⁰ C and +50 ⁰ G is located, is reacted,

For selective substitution on the triazine skeleton, the procedure known for the stepwise substitution in 1,3,5-triazines is followed.

Ausführungsbe ispiel

The invention is explained in more detail below with reference to some examples.

example 1

2-Ohlor-A-et hyl on in 0-6-cy c 1 op enty 1 amino-s-tr 1 az in

Water (distilled water), initially introduced in 250 parts by weight of ¹ liter of water, is added to a solution of 46 parts by weight, prepared at room temperature. Cyanuric chloride in 250 parts by weight Dropped acetone at 0 ⁰ G and the corresponding fine suspension with a cryogenic mixture (preferably with C0 ₂ / alcohol) to -10 ⁰ C cooled.

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In the suspension thus prepared, 23 parts by weight. Cyclopentylamin as a 50% aqueous solution with vigorous stirring and discharging the Ee act ion sw poor dripped and stirred for half an hour. Thereafter, the equivalent amount of a 30% aqueous sodium hydroxide solution is added dropwise into the acidic mixture until a pH of from B to 9 has been established.

For the addition of the sodium hydroxide solution, about 30 minutes are required in the case of the abovementioned amounts used. The reaction product is present as a well-distributed suspension.

Then 12 parts by weight. Ethylamine added as a 50% aqueous solution at -10 ⁰ C with vigorous stirring. Subsequently, the temperature is raised to 25 to 30 ⁰ C and stirred for 1 hour at this temperature.

After this treatment, a pH of about 3 sets. Then - in the course of about 2 hours - neutralized with equivalent amounts of 30% aqueous sodium hydroxide solution. Towards the end of the neutralization, the pH rises to 9, whereas previously it remained constant at about 8 in the case of about 80 % of the sodium hydroxide solution used.

Then the acetone present in the reaction slurry - finally by stripping with nitrogen - removed at 30 ⁰ G. The remaining white product is filtered off with suction and the precipitate 4 to 5 times with distilled water. salt-free washed Subsequently the granular product at 50 ⁰ O is dried in vacuo. The yield is about 95 % of theory.

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Analogously, other members of the cycloalikylamino-triazines of this invention can be prepared * A selection of which is included in Table 2a, (p.11 and 12), including Example 1.

Therein mean in Examples 16 to 20:

= 2,2,4- or 2,4,4-trimethylcyclopentyl

GH.

or

in Examples 21 to 26j TMG = 3,3,5-trimethylcyclohexyl CH

(In this group there are stable cis and trans forms and -) mixtures).

in Example 27:

Δ 2,3- £ MC BA = 1,5,5-Tr-imethyl-2,3-glyc1-hesenyl-1-methyl-

amino-

' ^v GH ₃

CH ₂ - Ij -GH ₃ GH ₃

In Example 28 to

IPAA = isophoronaminoalcohol

= 1,5,5-trimethyl-3-oxy-1-methylamino-cyclohesyl

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and in example 21 and 32s ·. ·

IPSAA = isophorone epoxidiaminoalcohol = 2,4,4-irimethyl-2-oxy-o-oxo-oxyolated lamino

Table 2b (see Figures 13 and 13a) indicates the substituents of these compounds with respect to formula I, as well as their melting points.

Table 2a shows the chlorocycloalkyl-s-triazines prepared

Example 1 = 2-chloro-4-ethylamino-6-cyclopentylamino-s

"triazine

Example 2 = 2-Chloro-4-amino-6-cyclopentylam: Lno-s-triazine Example 3 = a-chloro-1-methylamino-e-cyclopentylamino-s

triasine Example 4 = 2-chloro-4-dimethylamine: Lno-6-cyclopentylamino-s

triazine Example 5 = 2-chloro-4-isopropylamino-6-glylopentylamino-s

Example 6 = 2-Chloro-4-n-propylamino-6-GyGlopentylamino-s

triazine Example 7 = 2-chloro-4-ethanola] Ilino-6-cyclopentylamino-s

triazine

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Example 8> = 2-Chloro-4- (2-methoxy-ethylamino) -6-cyclopentyl-

amino-s-tr i az in Example 9 = 2-O-chloro-4 - (3-methoxy-propyl-amino) -6-cyclopentyl-

amino-s-tr i azine Example 10 = 2-chloro-4- (3-ethoxypropyl-i-diolino) ~ 6-oxy-lopentyl

amino-s-triazine Example 11 = 2-Chloro-4- (3-n-butoxy-1-propylamino) -6-gyolopene

tylamino-s-triazine Example 12 = 2-Chloro-4- (3-n-he2yloxy-1-propyl-amino) -6-cyclo-

'pentylamino-s-triazine Example 13 a 2-C] alor-4- (3-isopropoxy-1-propyl-i-diolino) -6-glycine

pentylamino-s-triaz in Example 14 = 2-Ciilor-4- (3-isobutoxy-1-propylamino) -6-cyGlo-

pentylamino-s-triazine

Example 15 - 2-Chloro-4-methoxy-6-GyGlopentylamino _! s-triaine Example 16 = 2-Chloro-4-amino-6-- ⁽ I) MCP-amino-s-triazine Example 17 = 2-Chloro-4-methylamino-6-2MQP-amino-s-triazine Example 18 = 2-chloro-4-ethylamino-6-TMCP-α2-olno-s-triazine Example 19 = 2-Glilor-4-isopropyl-1a-Jaao-6-TMCP-amino-s-triazine Example 20 = 2 chloro-4- (2-methosy - etb.ylamino) -6-amino ^ ⁱ RMAP

s-triazine

Example 21 = 2-chloro-4-methylamino-e-trans-TMC-amino-a-triazine Example 22 = 2-chloro-4-isopropylamino-6-tans-TMO-aJ3lino-s

• triazine

Example 23 = 2-chloro-4-methylamino-6-Gis-TMC-amino-s-1; riazine Example 24 = 2-0) ilor-4-dimethyl-i-amino-e-TMC-amino-s-triazine Example 25 = 2 Glomo-4-ethylamino-6-TMC-amino-s-triazine Example 26 = 2-Chloro-4-ethanolamino-6-ois-TMC-anino-s-triazine Example 27 = 2-Glilox ^! 4-isopropylaiaino-6- (2,3-TMC SA) -s-tri-

azine

Example 28 = 2-GllloΓ-4-methyl-2-lino-6-IPAA-s-tΓiazine Example 29 = 2-chloro-4-etllyla-lino-6-I? AA-s-tΓiazine.

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Example 30 = 2-chloro-4-isopropylamino-6-IPAA-s-triazine

Example 31 = 2-chloro-4-ethyl-amino-6-IPBAA.-s-triazine

Example 32 = 2-chloro-isopropylamino-6-IPSM-s-triazine

Example 33 = 2-glilor-4- _i- 6-bis-cyclopentylamino-s-tria2;

Table 2b List of the compounds prepared with their various substituents and other parameters according to formula I and their melting points

For example, IL · Rp Eq P "A η Melting range position

Nr.- ^'J * of

1HH-CH ₂ CH ₃ O-CH ₂ -O-185-188

2 HH -H "0 -CH ₂ -O-125-128

HH 3 -CH ₃ O -CH ₂ - O - 140-144

4H GH ₃ -GH ₃ O -GH ₂ - O - 36-38

5 HH -GH = (GH ₃ ) ₂ O -GH ₂ - O - 162-164

6 HH -GH ₂ -CH ₂ -CH ₃ O-CH ₂ - O- - 163-167

7 HH -GH ₂ -CH ₂ -OH 0 -CH ₂ - 0 - 115-117

8 HH -CH ₂ -CH ₂ -OCH ₃ O -GH ₂ - O - 80-85

9 HH -CH ₂ -GH ₂ -CH ₂ OGH ₃ 0 -GH ₂ - 0 - 95-97

HH -OH ₂ -CH ₂ -GH ₂ OCH ₂ -CH ₃ 0 -CH ₂ - 0 75 - 78

II II -GH ₂ -GII ₂ -CH ₂ OOH ₂ - 0 -GH ₂ - 0 - 84 - 86

CH ₂ -GH ₂ -CH ₃

HH -CH ₂ -GH ₂ -GH ₂ -OCH ₂ - 0 -CH ₂ - 0 - 54 - 55

CHp-CHp-GHP GHP-CHO

HH -.CH ₂ -GH ₂ -CH ₂ -O-CH = O -CH ₂ - O - 105 - IO9

HH -CH ₀ CHO CH CHO O ₀ -O-CH ₀ - O - 95-100

CTi CD • VJI Cö UJ U)

Continuation Table 2b _R ^E 2 H e P A n Position of E " melting range Ex, C H R = -CHo / -OH / = O No. H H -OCHO O -CH ₂ - O , - .. 53 - 55 15 H- H -H- O -CH ₂ - 3 2,2,4 (2,4,4) 114 ~ 119 16 H H -CH ₃ O -CH ₂ - 3 2,2,4 (2,4,4) 134-138 17 H H -CH ₀ -CHo O -CH ₂ - 3 2,2,4 (2,4,4) 94 - 98 18 H H O -CH ₂ - 3 2,2,4 (2,4,4) 106-113 19 H H -CH ₂ -CH ₂ -O-CHo O -CH ₂ - 3 2,2,4 (2,4fr) 35 ~ 40 20 H H -CH ₃ O -CH ₂ -OH ₂ - 3 3,3,5 (trans) 139 - 144 21 H CHO -CH = (OHo) ₂ O -OH ₂ -OH ₂ - 3 3,3,5 (trans) 54 - 56 22 H H O -OH ₂ -OH ₂ - 3 3,3,5 (ois) 163-170 23 H H -CH ₃ O -CHp-CHP 3 3,3,5 (mixture) 107-115 24 H H -CH ₂ -CH ₃ -. O -CH ₂ -CH ₂ - 3 3,3,5 ^ mixture) 122-125 25 H H -CH ₂ -CH ₂ -OH O -OH ₂ -CH ₂ - 3 3,3,5 (ice) 105-115 26 H H 1 -CH = OH- 3 1,5,5 122-127 27 H H -CH ₃ 1 -GH ₂ -CH ₂ - 4 1,5,5 / 3 169 - 173 28 H H -CH ₂ -Go 1 -OH ₂ -OH ₂ - 4 1,5,5 / 3 145 - 149 29 H II -OH = (CHo) ₂ 1 -GHp-CHP 4 1,5,5 / 3 105-109 30 H H -CH ₂ -CH- O -OH ₂ -OH ₂ - 6 2,4,4 / 3/6 156 - 160 31 H -CH = (CHo) ₂ O -CH ₂ -CH ₂ - 6 2,4,4 / 2/6, 145 - 149 32 H O -OH ₂ - O 193-195 33

ro cpi

Cr> CD

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The active compounds according to the invention can be used either individually or, with different substituents S 1, H _2, Kq and / or E, different meanings of A and / or B and / or different values of n, ia and / or p and / or q in mixture with one another. Of course, it is also possible to mix one or more of the active substances mentioned with other herbicides, fungicides, insecticides, growth regulators, etc., and apply the respective crops to them.

In addition, admixing with mineral fertilizers is possible, the easiest way to fertilizer solutions ».

Usually, the active compounds according to the invention are optionally added in the abovementioned mixtures - before the application aids from the group of carriers, diluents, solvents, wetting agents, adhesives, dispersants and / or emulsifiers, etc., and thereby the splashing, or Improve the enabling of a uniform distribution of the active ingredients.

Application of the active ingredients A greenhouse test series with 4 kg / ha

the (most of the listed on page 11 and 12) inventions to the invention compounds were carried out at a rate of 4 kg / ha, based on pure active substance, corresponding greenhouse house tests for Aokersenf, tomato, wild oats, millet and field sap.

The respectively required amounts of active ingredient were suspended in 1000 1 of water / ha.

O λ ^ O 0

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Pre-emergence was carried out on the surface before germination of the seeds and in the Ή ac frequent run on the leaf top flare in the second to third leaf stage.

Three weeks after the treatment, a very good action against dicotyledonous and monocotyledonous plants both in the forerun and at the casserole (Tables 3a and 3b) can be observed in the compounds according to the invention.

The evaluation of the test results was carried out by the

usual rating, where 1 = full effect = killing of the plants and

5 = no effect = plants - as untreated mean.

Surprisingly, in some compounds (Examples 4, 5 »15, 26, 27) the good tolerability against cruciferous vegetables z. B. Ackersenf, at the same time very good action against grasses (Elughafer, or field foxtail) in pre-emergence.

The selectivity to cruciferous vegetables is for some cultures, eg. B. for winter rape extremely interesting and for drugs based on s-triazines completely surprising.

B greenhouse experiments with smaller quantities and Vergleichschlett according to the prior art

For a larger number of test plants, similar experiments were carried out as in the series A with amounts of 2,1,1 / 2 and 1/4 kg of active ingredient / ha. Again, the geweilige amount of active ingredient in 1000 1 water / ha was distributed before application.

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As shown in Tables 4a and ^af and 4b and b ', both in the pre- and postemergence for the compounds of the invention excellent activity against grass weeds (eg., Arae, Elughafer, Windhalm and dicotyledonous weeds) can be observed.

In addition to this broad spectrum of activity, however, the surprisingly high compatibility for triazine compounds in cereal crops such as barley and / or wheat comes to light in pre-emergence,

The use of a compound of the invention as a soil herbicide in cereal crops has the specific effect against grass weeds the advantage that - in contrast to most previously known soil herbicides - in cereals simultaneously a particularly wide range of dicotyledonous weeds is detected.

Also surprising for triazine compound is the selectivity of some compounds of the invention in winter rapeseed pre-emergence (see Example 2, 5, 18, 19), simultaneously associated with a very good activity against field foxtail and an abundance of dicotyledonous weeds.

In addition, the good selectivity of the compounds according to the invention in some important other crops - such as maize, cotton, soybean, ice - in both pre-emergence and post-emergence is evident from Tables 4a to 4b ^f .

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G. Comparison with s-triazines of the prior art

Because of the high herbicidal activity of the compounds according to the invention, the application rates were additionally reduced to 1/8 and 1/16 kg / ha and tested in the greenhouse experiment together with comparison agents from the group of s-triazines.

As a standard comparison agent in these experiments atrazine (= 2 0hlor - ^ - ethylamino-6-isopropylamino-s-triazine) and terbutryn (= 2 methylthio - ^ - ethylamine-2tert. Butylamino-striazine) was used.

Table 5, which was determined in this test series, shows that the compounds according to the invention exceed the compounds of the prior art in important indications (such as field foxtail, windhoppers, chickweed or deadly nettle) in their herbicidal activity and, moreover, at the same time excellent compatibility with crops, inter alia in cereals, have compared to the above comparative examples «

In this series of experiments, as well as in B, it was observed in cultivated oats that the length of growth is inhibited without any impairment of the yield.

Advantages of the compounds of the invention

The advantage of the compounds of the invention is, inter alia, that the herbicidal activity of the comparison agent (1) (atrazine) z. B. against fieldfoot tail, ^T 3indhalm,! Wild oats, chickweed, chamomile and deadly nettle is reached or even exceeded, but on the other hand - especially in the Vorauf1auf procedure - in contrast to this comparison means a

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excellent selectivity in cereals, especially in barley and wheat, is achieved ·

Although the comparison (2) (terbutryn), also from the group of s-triazines, is approved for a pre-emergence application in lintergestreide in the Federal Republic, but the effect against grass weeds occurring in cereals, such as field foxtail and hawthorn, is significantly lower than that Compounds according to the invention (cf., in particular Table 4b).

None of the comparison means shows the selectivity observed in an amount of the compounds according to the invention

Winter rape.

The elongation inhibition in some cereals also allows the use of some of the compounds of the invention as a growth-regulating agent.

In addition, some of the new compounds have been found to have additional fungicidal activity.

Table 3a

Herbicidal activity of the compounds of the invention

various test plants pre-emergence application rate: 4 kg active ingredient / ha

Ackersenf tomato according to the invention

links 1 1 1 1 tail example 1 1 1 1 2 1 Example 2 1 1 1 1 1 Example 3 5 1 2 3 1 Example 4 1

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Example 5 5 1 1 1 1

Example 6 5 13 5 4

Example 7 5 1 5.45

Example 8 1 1 1 11

Example 9 1 1 1 1 1

Example 10 "2 1 1 2 1

Example 11 5 14 54

Example 12 5 2 5 5 4

Example I3 1 1 2 4 1

Example 14 5 1 4 5 4

Example 15 5 3 1 5 2

Example 16 3 1 1 1 '1

Example 17 5-5 5 5 2

Example 18 3 11 11

Example 19 1 1 1 2 1

Example 20 1 1 1 3 1

Example 21 5 5 4 5 2

Example 22 4-14 4 2

Example 23 5 5 3 4 1

Example 24 5 5 4 4 2

Example 25 3 4 3 3 1

Example 26 5 1 2 3 1

Example 27 5 1 '1 3 1

Example 28 2 1 1 3 2

Example 29 2 1 12 1

Example 30 4 3 4 5 1

Example 3I 3 2 3 2 1

Example 32 5 4 1 "3 1

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Table 3b

Herbicidal action of the compounds according to the invention on various test plants in the Nacaa run

Application rate j A-kg of active ingredient / ha

Yeast indigenous crops according to the invention

Tomato IPlug

oats

barnyardgrass

Foxtail

Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 Example 15 Example 16 Example 17 Example 18 Example 19 Example 20 Example 21 Example 22 Example 23 Example 24 Example 25 ,

1 1 1 2 1 1 1 1 1 1 1 1 1 1

3 1 1 1 2 1 1 1 1 2 1

1 1 1 1 1 1 1 1 1 1 1 1 1 1

1 2 1 4 3 5 4 1 1 4 4 4 5 4 3 4 5 4 4 2 5 3 4

1 4 1

3 1 1

1 1 4 4 1

5 3 1

4 1 2 1

3 1 2 3

- Ζ-ί- 61 853 18

20/6/83

example 26 1 example 27 1 example 28 2 example 29 * .1 example 30 1 example 31 3 example 32 ' 1

 12 4 2

3 5 5 4

114 1

14 3 3

14 3 3

113 3

'114 1

Table 4a Herbicidal action of the compounds according to the invention in the application rates of 2, 1, 1/2 and 1/4 kg of active ingredient / ha. Application before emergence of the plants (part 1),

Test plants Example 1 Example 2 Example 3 Example 5 Example 8 Example 9 kg active kg active kg active kg active kg active kg active substance ha substance ha substance ha substance ha substance ha substance ha Z 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4

charlock 1 3 3 3 1 1 4 5 1 1 1 1 1 1 3 1 4 3 5 5 1 1 4 5 3 3 3 3 ro f tomato 1 1 1 2 1 1 4 4 1 1 1 4 1 1 1 4 1 1 4 1 1 1 1 1 1 1 1 O I barnyardgrass 2 3 3 4 3 3 4 4 2 3 3 4 3 4 4 3 5 2 5 5 3 4 4 4 5 O \ CO U) oats 1 1 2 3 1 1 1 1 1 1 2 3 2 2 3 5 1 2 5 3 1 1 4 4 oats 1 1 1 1 1 1 1 1 1 1 1 1 1 3 3 3 1 1 2 2 1 1 2 5 Arable Fox Sohwanz 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 3 3 1 1 1 1 chickweed 1 1 2 3 1 1 1 1 1 1 1 1 1 1 1 3 1 1 1 1 1 1 1 1 Climbing lab herb 1 1 2 3 1 1 3 4 1 1 2 3 4 5 3 5 1 3 4 3 2 5 5 5 chamomile 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 (Ti White goosefoot 1 1 1 3 1 1 1 1 1 1 1 1 1 3 1 1 5 5 1 1 2 5 Windhalm 1 1 1 1 1 1 1 1 1 1 1 1 1 2 1 1 1 1 1 1 1 1 03 Ul UJ -Λ CO barley 3 3 5 5 3 4 3 5 3 4 3 5 5 5 1 1 4 5 1 1 3 4 wheat 3 4 5 5 4 4 4 4 3 3 3 5 5 5 3 4 5 3 1 1 3 5

Table 4a Herbicidal treatment of the compounds according to the invention in the application rates of 2, 1, 1/2 and 1/4 kg of active ingredient / ha · application before emergence of the plants

(Part 2).

Test plants Example 1 Example 2 Example 3 Example 5 Example 8 Example 9 active kg active kg active kg active kg active. kg active substance ha substance ha substance ha substance ha substance ha substance ha 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4

dead nettle 1 1 1 1 1 1 1 1 1 1 1 1 1 1 2 3 2 5 5 5 1 1 1 1 VJL 5 » • vetch 5 5 5 5 1 4 4 4 3 3 5 5 5 5 5 5 VJL 5 VJL 5 5 5 νπ 5 5 • VJi CB VO VjJ Amaranth 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 3 3 1 1 3 3 5 sugar beet 1 1 1 3 1 1 1 1 1 1 1 1 1 1 1 1 1 2 2 2 2 2 2 2 winter rape 1 1 3 5 4 4 5 .5 1 1 3 4 4 VJL 5 5 1 1 1 1 1 1 1 1 Seed weed flower 1 1 1 1 1 1 1 1 1 1 1 1 poppy 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 Flea-kitten rich 1 1 1 1 1 1 1 3 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 French herb 1 1 1 1 1 1 1 3 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 soy 3 4 5 5 3 4 4 4 3 4 5 VJL 3 3 4 5 3 4 VJL 5 4 4 5 cotton 5 5 5 5 3 5 5 5 5 5 5 5 3 4 5 5 5 VJL 5 5 4 5 5 eeis 1 3 3 3 1 2 3 3 1 3 3 3 4 4 4 4 VJL 5 5 5 5 · 5 5 Corn 5 5 5 5 5 5 VJL 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5

Table 4a Herbicidal action of the compounds according to the invention in the application rates of 2, 1, 1/2 and 1/4 kg of active ingredient / ha · application before emergence of the plants (Part 1).

Test plants Example 18 Example 19 Example 29

kg active ingredient ha kg active ingredient ha kg active ingredient ha 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4

Aokersenf 3 3 4 4 ul 3 5 ul 2 3 3 3 tomato 1 1 1 3 1 1 1 3 1 1 1 1 barnyardgrass 2 3 5 5 4 4 5 ul 2 4 5 5 oats 3 3 4 5 3 3 4 3 1 1 3 ul oats 1 3 4 5 ul 5 5 3 1 1 3 5 Fieldfoot tail 1 1 1 3 1 1 2 3 1 1 2 3 Line up 1 1 1 1 1 1 1 1 1 1 1 1 Klettenlab herb 3 3 4 4 4 4 4 5 5 ul 5 5 chamomile 1 1 1 2 1 1 1 2 1 1 1 1 White goosefoot 1 1 1 1 1 1 1 1 1 1 1 1 Windhalm 1 1 1 1 1 1 1 2 1 1 1 2 barley 5 5 5 5 5 3 ul 5 5 ul ul wheat 4 5 5 ul 3 5 3 5 5 ul 5 3

ro σ>

cn oo

• UI GO VjJ VjJ

Table 4a Herbicidal action of the compounds according to the invention in the application rates of 2, 1, 1/2 and 1/4 kg of active ingredient / ha. Application before emergence of the plants (part 2),

Test plants Example 18

kg of active ingredient ha 2 1 1/2 1/4

Example I9 Example 29 kg of active ingredient ha kg of active ingredient ha 2 1 1/2 1/4 2 1 1/2 1/4

Taubneesel 1 1 1 3 1 1 2 4 2 2 3 3 vetch VJL VJL VJL VJL 5 VJL VJL VJL 5 VJL VJL VJL Amaranth 1 1 1 2 1 1 1 3 1 1 1 3 sugar beet 1 1 4 4 1 2 4 4 VJL VJL VJL 5 winter rape 5 5 3 VJ! 5 5 VJL 1 2 4 VJL Saatwucher- flower 1 1 1 1 1 1 1 1 1 1 1 1 poppy 1 1 1 1 1 1 1 1 1 1 1 1 Flea knotweed 2 2 3 3 2 2 3 4 1 2 3 4 Iran p s enkraut 1 1 1 1 1 1 1 1 1 1 1 1 soy 3 4 5 5 4 VJL VJI 5 4 VJL 3 VJL cotton 5 5 VJL 5 VJL 3 5 VJL 5 VJL VJL VJI rice VJL VJL 5th 5 VJI 3 VJL 5 VJL 5 5 Corn 5 3 VJI VJL 5 3 VJL 5 VJ! VJL 5 VJL

Table 4b Herbicidal action of the compounds of the invention in the application rates of 2, 1, 1/2 and 1/4 kg of active ingredient / ha. Application after emergence of the plants (part 1).

Test plants Example 1 Example 2 Example 3 Example 5 Example 8 Example 9 kg active kg active kg active kg active kg effective kg active substance ha substance ha substance ha substance ha substance ha substance ha 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4

Aokersenf 1 1 1 1 1 3 4 4 1 1 1 1 1 1 2 4 1 1 1 1 1 1 1 1 tomato 1 1 1 1 1 1 3 4 1 1 1 1 1 1 1 5 1 * 1 1 1 1 1 1 1 barnyardgrass 1 2 3 3 VJL VJL 5 5 1 2 2 3 4 4 4 4 2 5 5 5 3 3 4 4 oats 1 1 3 4 1 1 1 2 1 1 3 4 1 1 1 5 1 1 4 5 1 1 3 4 oats 1 1 1 1 1 1 2 2 1 1 1 1 1 1 2 4 1 1 2 4 1 1 1 1 Aokerfuchs tail 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 2 4 1 1 1 1 chickweed 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 Klettenlab herb 1 1 2 3 1 1 4 4 1 1 2 2 1 1 2 3 1 2 4 4 1 1 4 5 chamomile 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 White goosefoot 1 1 1 1 1 1 2 4 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 Windhalm 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 barley 1 1 2 3 1 1 4 4 1 1 2 3 4 5 5 5 1 3 3 4 1 1 1 1 wheat 1 4 2 4 3 4 4 4 1 1 3 3 3 3 4 4 2 4 5 5 1 1 1 1

CO VjJ VjJ

Table 4b Herbicidal action of the compounds in accordance with the invention in the application rates of 2, 1, 1/2 and 1/4 kg of active ingredient / ha. Application after emergence of plants (part 2). '

Test plants Example 1 Example 2 Example 3 Example 5 Example 8 Example 9 kg active kg active kg active kg active kg effective kg active substance ha substance ha substance ha substance ha substance ha substance ha 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4

dead nettle

Amaranth

sugar beet

winter rape

corn marigold

poppy

Flea knotweed

French herb

cotton

Rice corn

111

3 4 5 111 111 111

11 1 111

111

1 1 Λ

3 3 4

3 4 4

4 4 5

2 1 1

1 1

1 4 4 5 5

111 4 4 4 111 111 111

1111

4 3 3 5

2 111

1111

3 111

1111 111 111 1111

111 1111

111

3 3 5

3 4 4

4 4 5

5 5 5

111 1

5 3 3 4

5 3 4 4

5 4 4 5

5 5 5 5

1113 5 4 4 5 12 2 3 1 113 1 111

111 4 4

5 5 4 5 5 5

4 111

5 5 5 5

4 2 2 3

5 12 2 3 114

1111

5 5 5 5

3 111 2 111

4 111

3111 1111 1111 1111

1111 5 3 5 5 5 3 4 5 5 5 5 5 5 5 5 5

1111 5 3 5 5 5 5 5 5 5 5 5 5 5 5 5 5

5 1 1 1

5 5 5 5

CO VjJ VjJ

Table 4b Herbicidal action of the compounds according to the invention in the application rates of 2, 1, 1/2 and 1/4 kg of active ingredient / ha. Application after emergence of plants (part 1),

Test plants Example 18 Example 19 Example 29

kg active ingredient ha kg active ingredient ha kg active ingredient ha 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4

charlock 1 1 1 1 1 , 2 3 4 1 1 1 1 tomato 1 1 1 1 1 1 2 2 1 1 1 1 barnyardgrass 1 1 3 ul 1 1 2 3 2 4 VJL ul oats 2 3 4 5 5 5 ul Ui 1 1 1 3 oats 1 1 2 3 1 3 3 5 1 1 1 3 Field Fox tail 1 1 1 1 1 • 1 2 3 1 1 2 3 chickweed 1 1 1 1 1 1 1 1 1 1 1 1 cleavers 2 2 3 4 4 5 5 ul ul 5 VJL 5 chamomile 1 1 1 1 1 1 1 1 1 1 1 1 White goosefoot 1 1 1 1 1 1 1 1 1 1 2 4 Windhalm 1 1 1 1 1 1 3 3 1 . 1 1 3 barley 4 VJL 5 UI 5 5 5 5 4 5 VJL ul wheat 3 VJL Ui Ui UI ul 5 UI ui ul ul ul

cn co

• VJl CD VjJ VjJ

Table 4b Herbicidal action of the compounds of the invention in the application rates of 2, 1, 1/2 and 1/4 kg of active ingredient / ha. Application after emergence of plants (part 2).

Test plants Example 18 Example I9 Example 29

kg active ingredient ha kg active ingredient ha kg active ingredient ha 1 1/2 1/4 2 1 1/2 1/4 2 1 1/2 1/4

dead nettle 1 1 1 1 1 2 3 3 1 1 3 3 vetch 4 VJL VJ! VJI VJL VJL VJL 5 2 4 4 VJL Amaranth 1 1 2 3 1 ' 1 2 3 1 1 3 3 sugar beet 1 1 1 1 1 2 3 VJL 2 2 2 2 winter rape 1 1 1 1 VJL VJL VJL VJL 1 1 1 3 poppy 1 1 1 1 1 1 1 1 1 1 1 1 Flea knotweed 1 1 1 1 1 1 1 1 1 1 1 3 French herb 1 1 1 1 1 1 1 1 1 1 1 1 soy 3 3 VJL VJL 3 3 5 3 3 3 4 4 cotton 3 4 4, VJL 3 4 4 VJL 5 "5 VJL rice 2 4 4 4 2 4 4 VJL 2 4 4 VJL Corn VJL VJL 3 VJL VJL VJL VJL 5 VJ! 5 VJT 3

CO UJ U)

Table 5 Herbicidal action of the compounds according to the invention in the application rates of 0.125 and 0.0625 kg / ha after application before ctem emergence (VA) or after emergence (NA) of the test plants

Verbin «kg Active- Acker- Wind- Flight- Bird- Camomile Oats Barley Wheat Wi-Eaps -, fabric / fuchs- halm oatmeal

^auns ha tail

VA NA VA NA VA NA VA NA VA NA VA NA VA NA VA NA VA NA

At -0.125 1 1 1 3 1 1 1 1 1 1 3 4 4 3 5 VJL 5 5 I play 1 _{O) O625} 2 2 2 4 1 , 4 1 1 1 1 VJL VJL 3 4 VJL 5 VJL VJI ci At -0.125 1 1 1 1 1 2 2 2 1 1 2 2 4 5 5 4 5 4 game 2 0.0625 1 2 1 1 1 3 2 2 1 1 2 1 4 5 VJL 4 5 4 At -0.125 1 1 1 2 1 1 1 1 1 1 3 4 4 3 VJL 5 5 3 game 3 0.0625 2 1 1 3 2 3 1 1 1 1 VJL 4 5 3 5 5 vn 3 Ver 0.125 equal to 0.0625 tel 1 2 3 1 3 1 2 3 4 4 5 1 2 1 3 2 3 1 2 1 1 2 3 1 1 cn cn 2 3 2 3 2 2 3 4 1 2

Oi125 2

gleichs-

iit- 0.0625 3

tel 2

Comparison means 1 Comparison means 2

1 3

4 4

3 4 2

4 5 4

3 1 5 1-

142 15

3 5

2 4 4 5

1 4

5 5

Atrazine Terbutryn

ro cn O cn CO • VJL CO U) VO

Claims (2)

R 1 is a straight- or branched-chain alkyl, alkoxy, alkoxyalkyl or alkylol radical or, preferably, an H atom, R 2 is a radical from the group of R 1 'or a radical, E, a radical from the group of E ^, preferably a Η-atom and R is a radical from the group of alkyls or alkoxides having one to three C atoms or hydroxyl or - to some extent as a derivative of 2: OH groups on the same C-Atoia - the oxo group and A = -CH 2 -, -CH 2 -CH 2 - or -CH = CH-, B ss -CH 2 -, -CH 2 -CH 2 - or -CH = CH-, η for A = -CH 2 - in each case O or 1, 2, 3, 4, 5 or 6 or for A? £ -CH2- each 3 »4» 5 or 6 and 61 853 18 20.6.83 m each 0 or 1, 2, 3 »4, 5 or 6, and ρ = either 0 or 1 and q = can be either 0 or 1 and wherein of the substituents E, - to E ^ at least one must be a Η-atom, and wherein the η or, m substituents B to the saturated or optionally also having a double bond having CyclοalkyIringen may be the same or different, in appropriate Application form for selective treatment of Hutzpflanzenkulturen with a broad spectrum of activity in weeds and grass weeds before and / or after emergence of the seed. 2. Use of mixtures of two or more active substances according to item 1 according to formula I, characterized in that the individual active ingredients by different substituents E / j, Eo, Ε-, and / or E, or A and / or B and / or the values of η and / or m and / or ρ and / or q differ from one another. 3. Use of one or more of the active ingredients according to item 1 or 2, characterized in that they are applied amounts of 0.05 to 10 kg / ha, preferably from 0.5 to 2.5 kg / ha. 4. Use of one or more of the active ingredients by item 1 and, if applicable, one or more of the items 1 or 2 and 3 », characterized in that the respective application form by admixing auxiliaries from the group of carrier, dilution, dissolution, Hetz-, 61 853 18 20.6.83 Adhesive, dispersing and Emuigiermittel wins. Use of one or more of the active substances according to item 1 and one or more of items 2 to 4, characterized by the admixture of substances from the group of herbicides, fungicides, insecticides, growth regulators, etc. 6. Use of one or more of the active ingredients by item 2 to 5, characterized in that they are used as an additive to mineral fertilizers.