DD157299A5 - PREPARATION HERBICIDE - Google Patents

Abstract

The invention relates to hydrocarbyl or Hydrocarbyloxyalkyl-2-haloacetanilides, herbicidal preparations containing these compounds as an active ingredient and their use in various crops such as planted rice and its weeds.

Description

Field of the invention: The invention relates to the field of 2-haloacetanilides and their use in agriculture, for example as herbicides, especially in the case of rice that has been harvested.

C characteristic of the known technical solutions:

The compounds of the present invention are characterized as 2-chloroacetanilides having a specific combination of an n-butoxy radical in an ortho position, an ethyl radical in the other ortho position, and as a substituent on the anilide nitrogen a radical selected from allyl, chloroallyl , Propargyl, .2-methoxyprop-2-yl or a radical of the formula -CHOR. in which R. is a C _1-1 . Alkyl radical means is selected.

The prior publications relevant to this invention contain numerous descriptions of 2-haloacetanilides which may be unsubstituted or substituted with a plurality of substituents on the anilide nitrogen atom and / or on the anilide ring, e.g. with alkyl, alkenyl, alkynyl, alkoxy, polyalkoxy, alkoxyalkyl, heterocyclyl, halogen or other radicals. The closest related known compounds in this field appear to be those in the following

-VB-

2284

No. 3,268,584, 3,442,945, 3,547,620, 3,773,492, 4,152,137 and BE-PS 810,763. However, in none of these known references do data on compounds of the type described herein be considered useful Herbicides for propagated rice, nor are the particular compounds of the invention described or proposed.

The known 2-haloacetanilides, the usefulness of which is known as herbicides in planted rice, differ substantially in their structure from those described here. In particular, all of these known herbicides possess lower alkyl radicals in both ortho positions to the anilide nitrogen atom, as well as an alkoxyalkyl radical on this nitrogen atom. These known Reisherb.izide are therefore related to those described neither related nor point out.

However, in order to have a basis for comparison, the relative herbicidal activity of compounds according to the invention is compared with that of the herbicide MACHETE (registered trademark of the Monsanto Company) whose active ingredient is 2 ', 6'-diethyl-N- (n-butoxymethyl) -2-chloroacetanilide (known as "butachlor"). Butachlor and a homologue thereof (here "EthyIbutachlor") sin.d described as rice herbicides in US-PS 3,663,200. Of the known 2-haloacetanilide

Herbicides is so far only "machete" commercially available.

-I / i

-A-

While known rice herbicides have proven useful, there is a continuing need for improved rice herbicides that control economically significant resistant weeds at lower rates and control or control such weeds for longer periods of time while preserving the harmlessness of the rice harvest and toxicity to the rice crop Fish and mammals is reduced.

It has been found that the above known herbicides have one or more undesirable properties in planted rice. Certain disadvantages of the known rice herbicides include their generally poor performance in the control and / or repression of the economically important resistant perennial weeds Cyperus serotinus, Eleocharis kuroguwai and Sagittaria trifolia, as well as diminishing efficacy in control or repression of annual weeds such as Echinochloa crus-galli and, to a lesser extent, Monochoria vaginalis, within a period of 2 to 6 weeks. These weaknesses are particularly evident at lower application rates, e.g. at up to 0.19 kg / ha and below. In fact, field tests have shown that for some treatments some of the known herbicides were unable to selectively control Eleocharis ku-roguwai at rates below 3 kg / ha or even 6 kg / ha for as short as 2 or 3 weeks. On

Similarly, in field tests it was also found that some known rice herbicides could not effect a definite repression of Sagittaria trifolia after U or 5 weeks.

Goal of the invention:

The invention therefore to provide _s a class of herbicides available that is particularly useful for fully planted rice to gave up.

The invention further relates to selected herbicides which

1. are harmless to propagated rice at levels up to at least 2.2H kg / ha (i.e., cause no more than about 15% damage); ·

2. selectively control Echinochloa crus-galli, Monochoria vaginalis ₅ Cyperus serotinus and Eleocharis kuroguwai; and

3. bring about an increased repression of Sapittaria trifolia.

Finally, an advantage of the herbicides according to the invention is that they are harmless and do not require any special handling measures.

These and other objects of the invention will be apparent from the following more detailed description.

28 40 7

Presentation of cles-.Wesens invention:

The invention relates to herbicidally active compounds, to herbicidal preparations which contain these compounds as active ingredient, and to herbicidal methods of application of these preparations in various crops, in particular in the case of planted rice.

It would now be found that a selective group of 2-haloacetanilides characterized by specific combinations of radicals on the anilide nitrogen atom, a specific alkoxy radical in an ortho position, and an ethyl radical in the other ortho position are unexpectedly superior and excellent have selective herbicidal properties as herbicides on planted rice compared to known herbicides of related structure, including a commercial rice herbicide.

A major feature of the compositions of the present invention is their ability to control and / or control annual and perennial narrow-leaved weeds in planted rice, in particular the prevalent and economically important annual weeds such as Echinochloa crus-galli and Monochoria vaginalis, as well as resistant perennial species such as Cyperus serotinus , Eleocharis kuroguwai, Sapittaria trifolia and other harmful weeds.

The compounds of the invention are characterized by the formula

Il

wherein R AlIyI _{5 is} chloroallyl, propargyl, 1-methoxyprop-2-yl or a radical of formula -CH ₉ OR ₁ wherein R "is allyl or a C _{1 r} alkyl- ₅ preferably C ₀ r Alky! radical.

Preferred compounds according to the invention are those in which R in the above formula is propargyl, 1-methoxyprop-2-yl, and also compounds in which R. denotes allyl, n-propyl, sec-butyl, 2-methylbutyl or isoamyl. Further compounds of the invention are those in which R of the above formula allyl, chloroallyl or -CH ^ OR.-groups, wherein R _{1 is} methyl, isopropyl, η-butyl or isobutyl

represents. - -

Execution sbei pi ele:

The usefulness of the compounds of the invention as active ingredients in herbicidal preparations prepared therewith, as well as methods for their use are described below.

The compounds of the invention can be prepared in various ways, e.g. by N-alkylating the anion of the appropriate secondary 2-haloacetanilide with an alkylating agent under basic conditions.

Example 1 describes the use of N-alkylation to prepare a compound of the invention. A modified N-alkylation process is described in Example 2 for the preparation of another compound of the invention. This method of Example 2 provides for the in situ preparation of halomethylalkyl or alkenyl ethers used as starting materials in the N-alkylation process.

example 1

5.4 g (0.02 mol) of 2'-n-butoxy-6'-ethyl-2-chloroacetanilide, 2.6 g (0.022 mol) of propargyl bromide and 2.0 g of benzyltriethylammonium chloride were mixed in 150 ml of methylene chloride and cooled. To the mixture at 15 ^° C., 45 ml of 50% NaOH was added all at once and stirred for 5 minutes, then 150 ml of cold water was added. The layers were separated, washed with water, then dried over MgSO ^ and evaporated by Kugelrohr to yield 4.45 g (73% yield) yellow oil, bp 118 ⁰ C.bei 0.03 mm Hg Elemental analysis:.. Calculated for C ₁₇ ClNO ₃ (I):

C: 66.33; H: 7.20; Cl: 11.52;

Found: C: 66.35; H:. 7.21; Cl: 11,50.

The product was identified as N-propargyl-2'-n-butoxy-6'-ethyl-2-chloroacetanilide.

Example 2

With virtually the same method as in Example 1 be written kylierungsmittel but using allyl bromide as Al, to give 4.9 g (79% yield) yellow oil, bp. 128 ⁰ C at O, 05 mm Hg, bulb tube.

Elemental Analysis: Calculated for G ₁₇ Hp ₄ ClNO ₇ (%):

C: 65.90; H: 7.81; Cl: 11.44; Found: C: 65.89; H: 7.81; Cl: 11.42.

The product was identified as N-allyl-2-n-butoxy-6'-ethyl-2-chloroacetanilide.

Example 3

In this example, a modification of the N-alkylation process described in Example 1 is presented. In this embodiment, the alkylating agent is formed in situ, making the process more efficient, economical and easier.

To a cooled mixture of 6.96 g (-0.12 mol) of allyl alcohol, 1.8 g (0.12 mol) of anhydrous paraformaldehyde and 150 ml of methylene chloride were added 4.71 g (0.06 mol) of acetyl chloride.

9? -ft A Π 7

give; the mixture was stirred for 90 minutes / until all paraformaldehyde was dissolved. 5.4 g (0.02 mol) of 2'-n-butoxy-6 ^I -ethyl-2-chloroacetanilide, 2.0 g of benzyltriethylammonium chloride and 50 ml of methylene chloride were then added to the mixture. The mixture was cooled to 100 ⁰ C and 50.ml 50% NaOH was added all at once and stirred for 15 min. The layers were separated, washed with water, over MgSO 4. dried and Kugelrohr evaporated, giving 6.0 g (92% yield) of clear oil, bp 122 ⁰ C at 0.04 mm Hg

Elemental analysis: Calculated for C ₁₈ H ₂₆ ClNO ₃ (%):

C: 63.61; H: 7.71; Cl: 10., 43; Found: C: 63.60; H: 7.74; Cl: 10.42.

The product was identified as N- {allyloxymethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide.

Example 4

By practically the same procedure as described in Example 3 but using 2-butanol as the alkylating agent, 4.15 g (78% yield) of clear oil, bp 118 ^° C. at 0.02 mm Hg (Kugelrohr) were obtained. Elemental Analysis: Calculated for C ₁ -QH ₃ ClNO., (%):

C: 64.12; H: 8.50; Cl: 9,96; Found: C: 64.05; H: 8.5.2; Cl: 9.90.

The product was identified as N- (sec-butoxymethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide.

The secondary anilide starting material used in the above examples is prepared by known methods, e.g. by haloacetylating the corresponding primary amine with haloacetylating agents such as a haloacetic halide or anhydride. Usually, the appropriate amount of the appropriate primary amine is dissolved in a solvent such as methylene chloride containing a base, e.g. Contains 10% NaOH, dissolved; it is stirred vigorously while reacting with a solution of the haloacetyl halide, e.g. Chloroacetyl chloride, with external cooling e.g. to 15-25 C mixes. The layers are separated and the organic solvent layer washed with water, dried and evaporated in vacuo.

The primary amines used to make the secondary anilides can also be prepared by known methods, e.g. by catalytic reduction of the corresponding suitably substituted nitrobenzene, e.g. 2-alkoxy-6-alkylnitrobenzene, in a solvent such as an alcohol, e.g. Ethanol, and using a platinum oxide catalyst.

Example 5

This example describes the preparation of N- (2-methoxyprop-2-yl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. - '

ΛΛ

228407 7

To a cooled solution of 4.4 g (0.016 mol) of N- (2-methoxyprop-2-yl) -2 ^L -n-butoxy-6'-ethylaniline in 0.0176 mol of 10% NaOH and 100 mL of CH ₂ Cl _{2 was} added dropwise 2 g (0.0176 mol) of chloroacetyl chloride; the solution was stirred for 10 minutes, the layers formed separated, and the organic phase washed with water over MgSO 4. Dried and evaporated with Kugelrohr, thereby obtaining 3.5 g (65% yield) of yellow oil, bp. 132 ⁰ C at 0.07 mm Hg

Elemental Analysis: Calculated for Cg ^H 28 ^C ^ ^NO 3 (%) ^:

C: 63.24; H: 8.26; Cl: 10.37; Found: C: 63.16; H: 8.27; Cl: 10.36.

The product was identified as the one listed above.

The secondary anilide starting material used in Example 5 is prepared by known methods (eg as described in the above-mentioned Belgian Patent 810,763). 19.3 g (0.1 mol) of 2'-n-butoxy-6'-ethylaniline were heated to 50 ⁰ C in 15 ml of ethanol and 15 ml of glacial acetic acid, then 9.68 g (0.11 mol) of methoxyacetone and 0.1 g of PtO _{2 was} added, and the mixture hydrogenated at 50 C for 4 h; The mixture was filtered off, evaporated with Kugelrohr at 100 ⁰ C and 0.07 mm Hg, giving a yellow oil

Elemental analysis: Calculated for C ₁₆ H ₂₇ NO ₂ (%):

C: 72.41; H: 10.25; N: 5.28; Found: C: 72.36; H: 10.27; N: 5.23.

2-0 -

The product was identified as N- (1-methoxyprop-2-yl) -2'-n-butoxy-6'-ethylaniline.

Examples 6 to 13

Using virtually the same procedure and conditions described in Examples 1-4, using the same secondary anilide and appropriate alkylating agents and amounts thereof, the corresponding products of Examples 6-13, which correspond to the formula in Table I, were obtained. manufactured. Examples 6 to 12 were prepared by the N-alkylation procedure described in Examples 3 and 4, the product of Example 13 was prepared by the N-alkylation procedure described in Examples 1 and 2.

Table I

ClCH ₂ C

C ₂ H ₅ J κ ?. ° ς 0-UC H _{4. 9} Elemental analysis Found (MmHg) / ' 64.96 Θ 137 Calculated 8.75 9.58 (0.04) , 64.94 64.06 8.53 10., 06 120 (0.03) 8.72 9.58 63,31 3,27 '10,42 117 (0.02) element 64.12 8.50 9.96 64.86 Si 72 Ί - Γ P 134 (0.03) C 63,24 8,26 10,37 9 _? 62 : ^{Χ C} 5 ^H 11 / H Cl 64.94 8.72 XC ₄ H ₉ C H Cl 9.58 Ti-C ₃ H ₇ C H. 'Cl CH ₃ -CH ₉ CHCH ₀ CHO C H Cl

Table I - Continuation Bp ° C (nmHg) Element - Elemental Analysis Calculated Found 64.05 8.49. 9.91 Example no. ^R l 128 (0.03) C H Cl 64.12 8.50 9.96 61.31 7.71 10.33 10 HC ₄ H ₉ 130 • '(0,04) c. H Cl 61.24 7.71 10.30 63.41 8.31 10.46 11 CH ₃ 119 - (0,02) C H Cl 63,24 8,26 10,37- 59.47 6.78 20 _; 52 12 ; ¹ ^ ₃ ¹ V 136 (ογυ 2   c H "Cl 5 9, '31 6.73. 20, .60 " 13 ' Cl t -CH ₀ C = CH

- 25 -

As mentioned above, the compounds of the present invention have proved effective as herbicides in planted rice against the major Asian weeds. However, herbicidal pre-emergence and post-emergence activity against other weeds in other crops has also been demonstrated. Tables II and III summarize the results of the tests carried out to determine the herbicidal pre-emergence activity of the compounds of the invention.

The pre-emergence tests were carried out as follows:

Good topsoil was placed in aluminum pans and tapped to 1-1.3 cm below the top. To the earth was given a certain number of seeds or offshoots of different plant species. The soil needed to fill the pans after applying the seeds and cuttings was weighed into a pan. The soil and a known amount of active ingredient, which was applied in the form of a solution or as a suspension of a wettable powder, were thoroughly mixed and used to cover the prepared pans. After treatment, the pans were placed on a greenhouse / where they were watered from below as needed, so that there was sufficient moisture for germination and growth.

About 2 weeks after sowing and treatment, the plants were inspected and the results recorded.

These are summarized in Tables II and m below. The evaluation of the herbicidal effect was obtained on the basis of a fixed scale based on% damage of each plant species. The ratings are as follows:

% Control

0-24 25 - 49 50 - 74 75 -

undetermined

Rating 0 1 2 3 5

The plant species used in a test series, for which the data are summarized in Table II, are marked with letters according to the following legend:

A Canada Thistle

B Cocklebur

C - Velvetleaf

D morning glory

E Lambsquarters

F smartweed

G yellow nutsedge

H Quackgrass

I Johnsongrass

J Downy Brome

K Barnyardgrass

Creeping thistle

Winds report

couch-grass

fluffy trespe

Cirsium arvense

Xanthium pensylvanicum Abutilon theophrasti Ipomoea sp. Chenopodium album Polygonum sp. Cyperus esculentus Agropyrum repens Sorghum halepense Bromus tectorum

Echinochloa crus-galli

1ϊ

1 • δ - 13 table II A B C Pflahzenspezies Έ F G H ¹ I j K Preemergence test 3 2 1 3 3 3 3 3 »3 3 Verb.von 2 9 3 2 1 D 3 2 .3 3 0 3 3 Ex. 3 2 2 2 3 3 3 3 3 3 3 No. 3 10 kg / ha 2 1 1 .2 1 1 3 2 0 3 3 11.2 5 0 1 3 * 2 2 3 3 3 3 3 4 11. 5.6 5 0 0 1 3 2 2 3 3 3 3 11.2 3 0 0 1 2 1 3 2 0 3 3 5 12 5.6 3 0 O' 0 1 2 2 3 0 3 3 - - - .. 11.2 5 0 1 0 • 3 2 3 3 5 3 3 6 ⁵ J ⁶ 5 0 0 0 Second 3 1 3 5 3 3 11.2 5 0 0 0 0 1 "3 0 3 3 7 5.6 5 0 .0 - 0 0 0 3 0 0 3 3 11.2 2 0 3 0 3 3 3 3 1 3 3 5.6 3. · 1 2 0 3 3 2 3 .1 3 3 11.2 3 0 0. 2 2 1 3 2 1 3 3 5.6 3 1 0 3 2 1 3 2 0 3 3 11.2 5 0 0 0 0 1 1 2 0 3 3 5.6 '5 0 0 0 0 0 0 0 0 Third 3 11.2 3 0 1 0 1 2 2 • 3 3 3 3 5.6 1 0 0 0 3  1 1 1 1 3 3 11.2 3 1 2 1 3 2 3 3 2 3 3 5.6 0 0 2 0 2 1 3 2 3 3 3 11.2 2 0 1 3 3 1 3 3 2 3 3 5.6 1 0 ' 1 2 1 1 3 2 1 3 3 11 _; 2 0 0 1 3 2 0 3 2 0 3 3 5.6 0 0 0 1 1 ' 0 0 1 0 3 3 11.2 0 5.6 0 11.2 5.6

 μ -

The compounds were further tested by the above method on the following plant species:

soybeans

sugar beets

wheat

rice

sorghum

L soybean

M sugarbeet

N 'Wheat

0 Rice

P sorghum

B Cocklebur

Q VJiId Buckwheat Winch Knotweed

D morning glory

R Hemp, sesbania

E Lambsquarters Report

F smartweed

C Velvetleaf

J Downy brome fluffy trespe

S Pariicum species

K Barnyardgrass

T Crabgrass

Xanthium pensylvanicum Polygonum convulvulus Ipomoea sp

 Sesbania exaltata Chenopodium album Polygonum sp

 Abutilon theophrasti Bromus tectorum Panicum spp

 Echinochloa crus-galli Digitaria sanguinalis

The results are summarized in Table III.

Verb.von Beisp.

kg / ha

5.6

1 ₇ 12 0.28 0.06 0.01

5.6 1.12 0.28 0.06

ojoi

5 ₇ 6 l _t 12 0 _T 08 · 0.56

5.6 1 _T 12 0.28 0 06 0.01

5.6

1.12 0.28

0.06 0.01

M N table P B III plant species D R e F C J S K T 3 3 preemergence 3 1 3 3 3 3 2 3 ~ 3 3 5 2 3 3 0 : - test 0 3 3 2 0 3 3 3 5 L 2 3 O 2 0 0 3 3 3 0 3 3 3 5 2 0 1 3 0 0 Q 0 0 0 0 0 2 1 3 5 0 0 0 3 0 1 2 0 0 0 0 0 0 0 2 5 1 3 3 2 3 0 2 1 2 3 3 0 3 3 3 5 0 3 2 1' 3 0 1 0 1 3 2 0 3 3 3 5 0 2 2 0 1 0 0 0 0 1 0 0 3 2 3 5 0 1 0 3 0 5 0 0 0 0 ' 0 0 1 0 2 5 0 1 O*· 3 0 0 2 0 0 0 0 0 0 0 2 5 0 2 3 3 3 ' 0 1 0 1- , 3 3 1 3 3 3 5 0- 1 2 1 1 0 0 • ι , 0 2 1 0 · 3 3 3 5 0 1 1 0 • 1 0 0 0 0 1 0 0 3 3 3 5 0 0 0 3 0 0 0 O· 0 0 1 0 ;O 0 3 5 5 2 3 2 3 0 3 0 2 2 2 0 • 3 3 3 5 0 0 1 2 0 0 1 0 1 0 0 0 3. 2 3 5 0 1 0 0 0 0 0 0 0 0 0 0 2 1 3 5 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 1 0 0 1 0 0 0 0 0 0 0 0 .. 5 ο · 2 3 0 3 0 0 1 2 3 3 1 3 3 3 5 0 O 2 Q 3 0 0 0 0 1 1 0 3 3 3 5 0 0 0 0 0 0 0 • 0- , 0 0 0 0 2 3 3 5 0 0 0 3 0 0 0 0 0 0 0 0 1 0 2 5 0 0 0 2 0 0 1 O· 0 0 0 0 1 0 1 5 0 1 1 0 0 0 0 • 0 0 0

Table III - continued

Verb.von Ex. No. kg / ha 6 5 _r 6, 1.12 0.28 0.06 7 '. 5.6 · ι; ΐ2 0.28 0.06 ö; oi 8th . "5.6 1.12 0.28 o; o6 O ₁ oil 9 5.6 1.12 0.28 10 ι 5.6 1.12 0.28 0; 06 5.6 1.12 0.28

M N preemergence P B - Q test plant species D R e F C J S K T 1 2 1 0 0 1 0 0 0 0 3 3 3 5 · L 0 o - O 0 0 0 0 0 0 0 0 3 3 3 5th 0 0 0 1 0 0 0 0 0 3 0 0 2 0 3 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 3 2 0 3 2 2 3 3 3 3 1 3 3 3 3, 0 2 1 0 3 0 1 1 3 3 1 0 3 3 3 ³ ν 1 1 0 3 3 0 1 0 2 0 0 0 3 3 3 3 ^ g 0 1 0 2 1 0 1 0 1 0 0 0 1 2 3 3, 0 0 "0 1 • 0 0 1 0 1 0 '0 0 0 , 1 2 1 0 2 3 0 • 3 "0" 3 1 ·" "2" - '3'. ^; '3 0 '. 3 3 ·.  '3 - 5 0 0 2 0 Second 0 2 , 0 2 0 1 " 0 3 3 3 5 1 0 0 3 1. 0 0 0 0 0 0 0 3 3 3 5. 0 0 0 3 0 0 0 0 0 0 0 0 · 1' 0 3 5 0 0 0 1 0 0 · 0 0 0 0 0 0 1 0 0 5 · 0 1 1 0 1 '0. 1 0 1 1 0 0 " 3 3 3 5 0 1 0 0 0 0 0 0 2 3 1 1 3 1 3 5 t 0 0 0 1 0 O· 0 0 0 0   0 0 1 0 0 0 0 0 0 0 0 0 0 * 0 0 0 0 0 0 0 5 ^r b ί 2 0 3 0 1 0 1 1 ' 1 0 3 · 3 3 5. 0 ο 1 0 1 0 0 Ö 3 0 0 0 3 2 3 £ 5 0 0 0 2 0 0 0 0 0 0 0 0 2 1 3 5 fm 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 5 ^ * 0 3 3 0 3 0 1 3 3 3 3 1 3 3 3 5 ^ 0 3 2 0 3 0 1 1 1 2 2 0 3 3 3 5 0 2 .0 3 • 2 0 1 0 2 2 1 0 3 3 3 5 0 3 0 2

Table III - continued

Verb.von Beisp.

kg / ha

5.6 1 12 O ¹ , 28 0.06 O ₇ oil

5.6 1.12 0.28 0.06 0.01

M N preemergence P B - Q test plant species D 'R e F C J S K T 3 3 3 0 2 1 2 2 2 0. 3 3 3 5 L 2 2 0 1 0 1 0 1 · 2 1 0 3 3 3 5 O 1 O 3 0 0 0 0 0 0 0 0 3 1 3 5 O O O 3 0 0 0 0 0 0 0 0 0 1 · 1 5 O O O 2 0 0 0 0 0 r \ O .0 0 0 0 1 5 O 2 3 0 2 0 2 1 2 3 1 0 3 3 3 5 O 1 2 0 1 0 2 0 2 1 0 0 3 3 3 5 O O ' 1 3 0 0 0 0 1 0 0 0 3 1 - 3- 5 O O Ο ·. · 2 0 0 0 0 0 0 0 0 0 0 " 0 5 O O 0 1 0 0 0 0 -0 0 0 0 0 0 Ό 5 O 0 O 0

It has been found that the herbicides of the present invention have unexpectedly superior properties as herbicides in planted rice, particularly for the effective selective control of the economically important resistant annual herbaceous weeds Echinochloa crus-galli and Monochoria vaginalis. and the perennial Cyperus serotinus (with one or two exceptions) and Eleocharis kuroguwai, while in some cases repelled the perennial weed Sagittaria trifolia to a greater extent than the commercial herbicide MACHETE, and also controlled many other less resistant annual and annual weeds pushed back ..

In order to illustrate the unexpectedly superior properties of the compounds of the invention both on an absolute and relative basis, comparative tests were conducted in the greenhouse. For comparison, MACHETE (currently the only commercially available 2-haloacetanidine rice herbicide) was tested.

i? _ 228 40

- -3Ί -

In the following discussion of the data, reference is made to herbicidal application rates represented by "GR ₁₅ " and ¹¹ GR g ₅ ", which are given in kg / ha, dividing by 1.12 in lbs / A can be transformed. GR ₁ C defines the maximum amount of herbicide which is necessary so that damage occurs at 15% or less of the crop, while GRg ₅ is the necessary minimum amount, to which a 85% inhibition of weeds is achieved. the GR ₁ ^ and GRor levels are used as a measure of the potential performance of commercially available products, it being understood that suitable commercial herbicides may exhibit greater or lesser plant damage within reasonable limits.

Another indication of the effectiveness of a chemical as a selective herbicide is the "selectivity factor"("SF") for a herbicide in certain crops and weeds. It is a measure of the relative degree of harmlessness to crops or _weed harm, and is expressed as the ratio GR _1t - / GR _8c -, ie GR ₁ ^ amount for the crop divided by the GR _ß5 amount for the weed , both quantities expressed in kg / ha.

Since crop plant tolerance and weed control are related, a brief discussion of this ratio, expressed as a selectivity factor, is appropriate. In general, it is desirable that the safety factors for the crop, i. the herbicide tolerance levels are high because, for one reason or another, higher herbicide concentrations are often desired. Conversely, the quantities for the weeds

· rf * ^

for economic and possibly ecological reasons, be small, i. the herbicide should have high unit activity. However, small amounts of herbicide may not be sufficient to control certain weeds, and more is needed. Therefore, the best herbicides are those that control the largest number of weeds with the least amount of application and the greatest possible harmlessness to the crop, i. Crop tolerance. The selectivity factors (defined above) are thus used to quantify the relationship between crop harmlessness and control of weeds; the higher the numerical value, the higher the selectivity of the herbicide for the weed control in a particular culture.

In a comparison test in the greenhouse, data were obtained for herbicidal activity, they are in Table IV put together. The relative effectiveness of the compounds of Examples 1,3 to 6, 8 and 9, which are exemplary compounds of the invention, with butachlor (active ingredient in the commercial rice herbicide MACHETE) as selective herbicides against economically important Asian weeds, usually associated with planted rice , compared.

ZS.

228407 7

The procedure used in this greenhouse test was as follows: Ray silt loam topsoil containing about G, 05 wt% Krillium and sieved through a 0.6 cm sieve was smoked about 5-10 days prior to use. Pots were filled with this soil so far that 2.54 cm remained free for flooding with water. Two to three week old rice plants (Bluebelle) were transplanted into these pots, as well as onions and seeds of the test weeds. The pots were then flooded with water and the test chemical applied to the surface of the water. The waterpic. gel was lowered so that the Echinochloa crus-galli seeds could rise, then it was lifted again and held in this position. The percent inhibition was determined using a scale of 0-100% at about 3 weeks post-treatment (WAT = weeks post-treatment).

The data presented in Table IV represent the percentage inhibition of plants within the application limits of 0.28 kg / ha to 2.24 kg / ha. The data are, as stated above, for rice and the weeds respectively as GR.r resp . GR expressed _fit; the selectivity factors are given in parenthesis below each weed; "NS" means non-selective within the rate limit. The level of control over Sagittaria trifolia, one of the major economic problem weeds and that of the perennial test weeds most resistant to 2-haloacetamide,

ZIS

is compiled in the last column of Table IV; The stated percentage control is achieved at the maximum test load of 2.24 kg / ha. The weed species. are identified as follows: Echinochloa crus-galli (EC), Monochoria vaginalis (MV), Cyperus serotinus (CS), Eleocharis kuroguwai (EK), and Sagittaria trifolia (ST).

GR ₁ , - Quantity (kg / ha) of rice EC MV Table IV EK ST ST control - at 2.24 kg / ha (%) connection 2.24 <O, 28 <O, 25 GRg ₅ Quantity (kg / ha) CS 0.4 (5.0) > 2.24 (NS). 15 butachlor 2.24 <O, 28 <O, 28 0.25 <O, 28 > 2.24 (NS) 65 Ex. 1 > 2.24 <O, 28 <O, 28 <O, 28 <O, 28 > 2.24 (NS) 30 Ex. 3 ^ 2.24 <O, 28 <O, 28 <O, 28 <O _r 28 > 2.24 (NS) 20 Ex. 4 7 * 2.24 <O, 28 <O, 28 <O, 28 <O, 28 > 2.24 (NS) 10 Ex. 5 > 2.0 <O, 28 <O, 28 0.28 0.43 > 2.24 (NS) 10 Ex. 6 1.96. <O, 28 <O, 28 <O, 28 <O, 28 > 2.24 (NS) 70 Ex. 8 1.87 <O, 28 <O, 28 <O, 28 0.86 (1.9) > 2.24 (NS) 25 Ex. 9 0.31 (5.4)

The files of Table IV give various important advantages of the compounds of the invention over butachlor: 1.) Examples 3 to 6 had higher harmlessness factors for rice; 2.) Examples 1, 3 to 5 and 8 had higher selectivity factors over EK and 3.) Examples 1, 3, 4, 8 and 9 all showed a higher percentage control over ST than butachlor. The general superiority of the compounds of the invention, especially those Examples 1 and 3 to 6 versus the commercial herbicide is clear.

In a further comparison test in the greenhouse further compounds according to the invention were compared with butachlor as a standard herbicide for planted rice. The compounds of Examples 2, 7 and 10 to 13 and butachlor were tested by the method described above; the data are summarized in Table V.

GR ₁ η amount (kg / ha) of rice EC Table V MV GRq, - Quantity (kg / ha) CS EK ST ST control at 2.24 kg / ha connection 1.68 0.99 (1.7) 1.3 (1/3) > 2.24 (NS) 0.71 (2.4) > 2.24 (NS) 25 butachlor 1.8 <0.28 <O, 25 0.78 (2.6) 0.28 > 2.24 (NS) 10 ~ Ex. 2 > 2.24 <O, 28 <O, 43 <O, 52 (4,3) 0.47 (4.8) > 2.24 (NS) O Ex. 7 > 2.24 <O, 28 <O, 28 > 2.24 (NS) <O, 28 > 2.24 (NS) O. Ex. 10 1.12 <O, 28 (4.0) <O, 28 0,95 (1,2) 0.28 > 2.24 (NS) 10 Ex. 11 0.75 <O, 28 • <O, 28 '1.8 (NS) <O, 28 > 2.24 (NS). - 15 Ex. 12 • 1.12 <O, 28 <O, 28 1.0. (1,1). <O, 28 > 2.24 (NS) 20 · Ex. 13

Also, the test data of Table V revealed that each of the compounds of this invention had one or more advantages over butachlor: 1.) Examples 2, 7, and 10 showed higher harmlessness factors for rice and 2.) Each compound of the invention exhibited higher selectivity factors over EC, MV, CS (except example 10) and EK as butachlor. Although butachlor had higher harmlessness factors than Examples 11-13 and a higher percent control over ST than the compounds of the present invention, these benefits contrasted with significantly lower selectivity factors in most of the weeds tested. It should be noted that although the greenhouse and field tests vary from test to test (more in the greenhouse than on the field), the comparative data presented in the tables were obtained under identical conditions for all tested herbicides.

In a further comparison test in the greenhouse, the compound of Example 3 and Butachlor was tested on seeded upland rice, once with a maximum test load of 1.12 kg / ha and once again with a maximum test load of 2.24 kg / ha. Ha. As an average of the two tests, it was found that the compound of Example 3 selectively controlled Echinochloa crus-galli at 0.31 kg / ha, while the harmlessness for rice was maintained at a rate of> 1.43 kg / ha, which a selectivity factor

of at least 4.6. Butachlor (a commercial rice herbicide) required 0.7 kg / ha to selectively control the same weed while maintaining the harmlessness of rice at> 1.68 kg / ha, giving a selectivity factor of at least 2.4 ie about half the selectivity factor of the compound of Example 3,

In further greenhouse tests, the compound of Example 3 was tested for activity against annual weeds in sugar beets at test load levels within the range of 0.07 to 1.12 kg / ha. The quantities of GR ₁₅ and GRg ₅ for sugar beet and the various weeds are shown in Table VI; the selectivity factors for the herbicide against the weeds in sugar beet are given in parenthesis below the weeds; "NS" means non-selective within the test amount limits. The following abbreviations are used in the table: Echinochloa crus-galli (BYG), Avena fatua (wo), Downy Trespe (DB), Arananthus retroflexus (RRP), Alopecurus / BG), Digitaria s. (LCG).

and yellow foxtail (YFT).

Table VI

GR ₁ J- manganese GR _ß ^ Quantity (kg / ha) ·, (kg / ha)

Sugar beets BYG WO DB RRP BG .- LCG YFT

> 1.12 <0.07 0.28 0.21 XI, 12 0.14 0.14 0.14 (> 16) (> 4) (> 5.3) (NS) (> 8) (> 8 ) (> 8)

The data of Table VI show that the compound of Example 3 selectively controlled each tested weed except Amaranthus retroflexus at rates well below 1.12 kg / ha, demonstrating the versatility of this compound as an effective herbicide in important crops.

The compounds of the present invention can be safely used with the normal care required for the handling of herbicidal preparations; special arrangements are not necessary.

The detailed description shows that the compounds according to the invention had unexpected and extremely superior herbicidal properties, both in absolute terms and in comparison with. structurally related known compounds, one of which (butachlor) is the active ingredient in a commercial herbicide. In particular, the compounds according to the invention proved to be excellent selective herbicides, especially in the control of economically important annual and perennial Asian weeds in planted rice. Above all, the compounds of the present invention show excellent control of the annual grasses Echinochloa crus-galli and Monochoria vaginalis, as well as perennial weeds such as Cyperus serotinus, Eleocharis kuroguwai _f and some compounds-are particularly effective against Sagittaria trifolia, while others less; resistant

control and / or restrain one-year grasses and perennial weeds, including those mentioned in Tables II, III and VI above.

The herbicidal preparations according to the invention, including the concentrates which have to be diluted before use, contain at least one active substance and one adjuvant in liquid or solid form. The formulations are prepared by mixing the active ingredient with an adjuvant comprising diluents, diluents, carriers and conditioning agents to formulate preparations in the form of finely divided solid particles, granules, pellets, solutions, dispersions or emulsions. Thus, the active ingredient can with an adjuvant such as a finely divided solid, a liquid of organic origin, water. a wetting agent, a dispersing agent, an emulsifying agent or a suitable combination thereof.

The compositions of the present invention, especially liquids and wettable powders, preferably contain as conditioning agents one or more surface-active agents in amounts sufficient to render a particular formulation readily dispersible in water or oil. The inclusion of a surface-active agent in the preparations promotes their effectiveness significantly. The term "surfactant" includes wetting agents, dispersants, suspending agents and emulsifying agents. Anionic, cationic and nonionic agents can be used equally.

Preferred wetting agents are alkylbenzene and alkylnaphthalenesulfonates, sulfated fatty acid alcohols, amines or acid amides, long-chain acid esters of sodium isothionate, sodium sulfosuccinate esters, sulfated or sulfonated fatty acid esters, petroleum sulfonates, sulfonated vegetable oils, ditertiary acetylenic glycols, polyoxyethylene derivatives of alkylphenols (especially isooctylphenol and Nonylphenol) and polyoxyethylene derivatives of the higher fatty acid monoesters of hexitol anhydrides (eg sorbitan). Preferred dispersants are methylcellulose, polyvinyl alcohol, sodium ligninsulfonates, polymeric alkylnaphthalenesulfonates, sodium naphthalenesulfonate, and polymethylene bisnaphthalenesulfonates.

Wettable powders are water dispersible formulations containing one or more active agents, an inert stretched solid, and one or more wetting and dispersing agents. The inert yield solids are usually of mineral origin, e.g. natural clays, diatomaceous earth and synthetic minerals of silica and the like. Such extenders include kaolinites, attapulgite clay and synthetic potassium silicate. The wettable powders of the invention usually contain from about 0.5 to 60 parts (preferably 5 to 20 parts) of active ingredient, about 0.25 to 25 parts (preferably 1 to 15 parts) of wetting agent, about 0.25 to 25 parts (preferably 1.0 to

- / 44

  ο

15 parts) of dispersant and 5 to about 95 parts · (preferably 5 to 50 parts) of inert stretched solid, all parts being by weight of the total formulation. If necessary, about 0.1 to 2 parts of the inert stretched solid may be replaced with a corrosion inhibitor or antifoam, or both.

Other formulations contain dust concentrates containing 0.1 to 60% by weight of active ingredient on a suitable diluent. These dusts may be diluted for use at concentrations of about 0.1 to 10% by weight.

Aqueous suspensions or emulsions can be prepared by stirring an aqueous mixture of a water-insoluble active ingredient and an emulsifying agent until uniform, and then homogenizing to obtain a stable emulsion of very finely divided particles The resulting concentrated aqueous suspension is characterized by its extremely small particle size so that after dilution and spraying the coating is very uniform. Suitable concentrations of these preparations contain about 0.1 to 60 wt.%, Preferably 5 to 50 wt.% Active ingredient, wherein the upper limit is determined by the Löslichkeitsgrenze of the active ingredient in the solvent.

In another type of aqueous suspensions, a water-immiscible herbicide is encapsulated so that an in

- / 45

2? _ 228407 7

- Λ5 -

an aqueous phase dispersed microcapsule phase is formed. In one embodiment, very small capsules are formed by combining an aqueous phase containing a lignosulfohate emulsifier, a water-immiscible chemical and polymethylene polyphenyl isocyanate, dispersing the non-water-immiscible phase in the aqueous phase, and then a poly-functional amine admits. The isocyanate and amine compounds react and form a solid urea shell around particles of the water-immiscible chemical to form microcapsules thereof. In general, the concentration of the encapsulated material is about 480 to 700 g / liter, preferably 480 to 600 g / liter of the whole preparation.

Concentrates are usually solutions of active ingredient in non-solvents or, only partially with water-miscible solvents, together with a surfactant. Suitable solvents for the active ingredient according to the invention include i.a. DimethyIformide, dimethylsulfoxide, N-methylpyrrolidone, hydrocarbons and water immiscible ethers, esters or ketones. However, other strong liquid concentrates may also be obtained by dissolving the active ingredient in a solvent and then diluting, e.g. with kerosene, to be prepared for spray concentration.

The concentrate preparations generally contain from about 0.1 to 9 parts (preferably from 5 to 60 parts) of active ingredient,

about 0.25 to 50 parts (preferably 1 to 25 parts) of surfactant and, if necessary, about H to 9H parts, solvent; all parts are by weight and based on the total weight of the emulsifiable oil.

Granules are physically stable particulate compositions containing an active agent adhered to or dispersed in a matrix of inert, finely divided, particulate extender. In order to assist the leaching of the active ingredient from the particles, a surface-active agent as listed above may be present in the preparation. Natural clays, pyrophyllites, illites and vermiculites are examples of useful types of particulate mineral diluents. Preferred extenders are porous, absorptive, preformed particles, such as pre-formed and sieved particulate attapulgite or heat-expanded, particulate vermiculite, and the finely-divided clays, such as kaolin clays, hydrogenated attapulgite or bentonite clays. These extenders are sprayed or mixed with the active ingredient to prepare the herbicidal granules.

The granule preparations according to the invention may contain about 0.1 to 30 parts by weight, preferably about 3 to 20 parts by weight of active ingredient per 100 parts by weight of clay and 0 to about 5 parts by weight of surfactant per 100 parts by weight of clay particles. ·. '·

p. 228 40? 7

The preparations according to the invention may also contain other additives, for example fertilizers, other herbicides or pesticides, protective substances and the like, which are used as adjuvants or in combination with one of the abovementioned adjuvants. Other herbicidally compounds which are useful in combination with the active compounds according to the invention, in particular in the case of planted rice, include, for example, methyl 5- (2,4-dichlorophenoxy) -2-nitrobenzoate (general name "Bifenox", active ingredient in the herbicide MODOWN®), 1 3-Dimethyl-4- (2,4-dichlorobenzoyl) -5-pyrazolyl-paratoluenesulfonate (code designation "SW-751"), α- (β-naphthoxy) -propicnanilide (code designation "MT-101), 2, ^{4-dichloro-3!} methoxy-4'-nitrodiphenylether (code-name "X-52"), 3,4-dichloropropionanilide (general term "propanil"), etc. For use in other than rice crops, other herbicidal compounds can Such compounds are, for example, triazines, ureas, carbamates, acetamides, acetanilides, uracils, acetic acid or phenol derivatives, thiolcarbamates, triazoles, benzoic acid, nitriles, biphenyl ethers and the like, such as, for example:

-IN THE

^{tof f} ' sulfur derivatives

2-chloro-M-e-thymine o-6-i s -propyl-amino-s-triazine 2-chloro-U> 6-bis- (isopropylarcino) -s-triazine 2-chloro-456-bis- (ethylamino) -s-triazine

3-isopropyl-lH ~ 2,1,3-benzothiadiazine-M- (3H) -one-2 _s 2-dioxide

3-Arnino-1,2,5-triazole

6,7-Dihydrodipyrido (1,2-a: 2 ', 1'-e) -pyrazidiinium salt 5-Bromo-3-isopropyl-6-methyluracil Γ, ^1- dimethyl-H ₅ U ¹ -bipyridine

5-tert-butyl-3- (2,4-dichloro-5-isopropoxyphenyl) -1, 3, 4-oxadiazol-2-one

ureas

N ¹ - (4-chlorophenoxy) -phenyl-NiN-dimethylurea N, N-dimethyl-N '- (3-chloro-4-methylphenyl) -urea 3- (3,4-dichlorophenyl) -1,1-dimethylurea 1 , S-Dimethyl-S- (2-benzothiazolyl) -urea 3- (p-Chlorophenyl) -1,1-dimethylurea 1-Butyl-3 ~ (3,4-dichlorophenyl) -1-methylurea

-Vf-

228407 7

Carbamates / Thiolcärbamate

2-Chloroallyldiethyldithiocarbairtate S - ^ - ChlorobenzyD-N, N-diethylthiolcarbamate Isopropyl-N-O-chlorophenyld-carbamate S-2,3-dichloroallyl-N, N-diisopropylthiolcarbamate Ethyl-N, N-dipropylthiolcarbamate.

S-Propyldipropylthiolcarbamat

Acetamide / acetanilides / Aniline / amides

2-chloro-N, N-diallylacetamide N, N-dimethyl-2,2-diphenylacetairide N- (2, U-dimethyl-5- [[(trifluoromethyl) -sulfonyl] -amino] -phenyl) -acetamide

N-isopropyl-2-chloroacetanilide

2 ¹ , 6'-diethyl-N-methoxymethyl-2-chloroacetanilide 2'-methyl-6'-ethyl-N- (2-methoxyprop-2-yl) -2-chloroacetanilide α, α, α-trifluoro-2, 6-dinitro-N, N-dipropyl-p-toluidine N- (1,1-dimethylpropynyl) -3,5-dichlorobenzamide

Acids / esters / alcohols

2,2-dichloropropionic acid 2-methyl-chlorophenoxyacetic acid U-2, M-dichlorophenoxyacetic acid methyl-2- [} ~ i (.2 U _{y-dichlorophenoxy)} phenoxy [] propionate 3-Amino-2,5-2- dichlorben2oesäure methoxy-3,6-dichlorobenzoic acid

iJ Η ·% J i · I

2,3,6 ~ trichlorophenylacetic acid N-l ~ naphthylphthalamic acid

Sodium 5- (2-chloro-4- (trifluoromethyl-phenoxy) -2-nitrobenzoate

456-dinitro-o-sec-butylphenol

N- (phosphonomethyl) glycine and sine C * - Honoalkylamin- and alkali metal salts and combinations thereof

ether

2, U-dichlorophenyl-M-nitrophenyl ether

2-Chloro-α, α ₅ α-trifluoro-p-tolyl-3-ethoxy-4-nitrodiphenyl ether

various

2,6-dichlorobenzonitrile. M & nona-sodium methane arsonate DinatriurniTiethanarsonat

228407

The herbicides of the present invention may be used singly, as mixtures with other herbicides, or in a particular order with other herbicides. Thus, for example, at treatments of planted rice crops with the herbicides according to the invention attach treatments with other herbicides or mixtures, e.g. with S-4-chlorobenzyldiethylthiocarbamate (generic term "benthiocarb") plus 2-chloro-4,6-di- (ethylamino) -1,3,5-triazine (general term "simazine") or 3-isopropyl- (1H ) benzo-2,1,3-thiadiazin-4-one-2,2-dioxide (generic name "bentazone") or 4- (4-chloro-2-methylphenoxy) butyric acid (general name "MCPB").

The main field of application of the compounds according to the invention is planted rice. However, as indicated by the test data for the compound of Example 3 in Table V, at least some compounds of this class can also be used in directly sown rice. However, due to the high unit activity of the compounds of this invention, directly seeded rice may be less tolerant to some of the compounds of this invention. It is therefore within the scope of the invention to combine these herbicides with protectants or antidotes to increase the tolerance of both planted and directly sown rice. Exemplary protective substances which are useful with the herbicides according to the invention.

see are u.a. the phenylglyoxylonitrile-2-oxime cyanomethyl ether described in US Pat. No. 4,152,137, 2,4-disubstituted-5-thiazolecarboxylic acids and their derivatives as described in US Pat. No. 4,199,506, and other rice protective agents for 2-haloacetanilides.

Fertilizers useful in combination with the active ingredients are e.g. Ammonium nitrate, urea, potash and superphosphate. Other useful additives are u.a. Substances in which plant organisms are rooted and grow, e.g. Compost, manure, humus, sand and the like

For herbicide formulations of the type described above, various exemplary embodiments are given below.

I. Emulsifiable concentrates

Wt.%

A. Compound of Example 1 50.0

Phosphate esters of ethoxylated alcohols

(e.g., GAFAC® RE-610) 4.125

Ethoxylated tertiary Ämin derived from fatty oils such as palm oil

{E.g. Ethomeen © C / 12) · Monochlorobenzene Cg aromatic solvent (T-400)

'' ": '.', 100,00

0 875 1 3, 5 3 1, 5

us

40 "

Wt.%

B. Compound of Example 3 46.45

GAFÄC® RE-61O '4,125

Ethomeen ^ C / 12 0.875

MCB 48.55

1OO, OO

C. Compound of Example No. 4: 5 Calcium dodecyl benzene oil onate / polyoxyethylene ether blend

(e.g., Atlox 3437F) 1.0

Xylene. 94.0

100.00

II. Liquid concentrates

Wt.%

A. Compound of Example No. 5 10.0

Xylene 90.0

100.0

B. Compound of Example No. 6 85.0

Dimethylsulfoxide 15.0

100.0

C. Compound of Example No. 7 50.0

N-methylpyrrolidone 50.0

100.0

D. Compound-of Example No. 8. 5.0 Ethoxylated Castor Oil 20.0 Rhodamine B * 0.5 Dimethylformamide 74.5

10.0,0

III. emulsions

A. Compound of Example No. 9 40.0

Polyoxyethylene / block

Copolymer with butanol (e.g., Tergitol XH) 4.0. Water. 56.0

B. Compound of Example No. 10, 5,0

Polyoxyethylene / polyoxypropylene

Block polymer with butanol. , 3.5

Water 91, 5

".100,0 '

IV. Wettable powders

' Wt.

A. Compound of Example No. 1 25.0 Sodium lignosulfonate 3.0 Sodium N-methyl-N-oleyl taurate 1.0

Amorphous silica (synthetic) 71.0

, 100.0

B. Compound of Example No. 3 80.0 sodium dioctylsulfosuccinate 1.25 calcium lignosulfonate 2.75 amorphous silica (synthetic) 16.00

100.00

C. Compound of Example No. 4 '10, O sodium lignosulfonate '. ' 3.0 sodium N-methyl-N-oleyl taurate 1.0 kaolinite clay' 86.0

_ £ _,. .228407

V. dusts

Wt.%

A. Compound of Example No. 10 '2.0 attapulgite. 98 _f O

100.0

B. Compound of Example No. 11 60.0 montmorillonite · 40.0

* 100.0

C. Compound of Example No. 12 '30.0 Bentonite · 70.0

100.0

D. Compound of Example No. 13 1.0 Diatomaceous earth 99.0

100.0

VI. granules

Wt.%

A ... compound of Example No. 1 15.0

Granulated attapulgite (20/40 sieve) 85.0

100.0

B. Compound of Example No. 3 '30.0

Diatomaceous earth (20/40) 70.0

;. , 100.0

C. Compound of Example No. 4 0.5

Bentonite (20/40) '. , 99.5

100.0

D. Compound of Example No. 5 '5.0

Pyrophyllite (20/40) x 95.0

100.0

r-jr »we fc« a » % ate ^ *% tß v

VII. Microcapsules

Wt.%

A. Compound of Example No. 1

encapsulated in polyurea shell. 49.2

Sodium lignosulfonate (e.g., Reax 88 B) 0.9

Water 49.9

B. Compound of Example No. 3

encapsulated in polyurea shell 10.0

Potassium lignosulfonate (e.g., Reax C-21) 0.5

Water 89.5

100.0

C. Compound of Example No. 4 80.0

encapsulated in polyurea shell magnesium salt of lignosulfate

(Treax. LTM) 2.0

Water 18.0

100.0

When used according to the invention, effective amounts of the acetanilides according to the invention are applied to the soil containing the plants or are taken up in a suitable manner in aqueous media. The application of the compositions as liquids and solid particles to the soil can be carried out by conventional methods, e.g. with motor atomizers, tank and hand sprayers or spray atomizers. Because of their effectiveness in low doses, the preparations can also be spread from airplanes as dust or spray. The application of herbicidal preparations to aquatic plants is usually carried out by adding the preparations to the aqueous medium in the area in the control of the aquatic plants

it is asked for.

The application of an effective amount of the preparations according to the invention at the site of the unwanted weeds is essential and critical for the use according to the invention. The exact amount of active substance to be used depends on various factors, e.g. the use in-aqueous medium or soil, the plant species and its stage of development, the nature and condition of the soil, the amount of rainfall and the specific acetanilide used. In selective pre-emergence application to plants or soil, an application rate of 0.02 to 11.2 kg / ha, preferably from about 0.04 to 5.60 kg / ha or 1.12 to 5.6 kg / ha is usually used Acetanilide used. In some cases, smaller or larger quantities may be sufficient or needed. In some tests with seeded upland rice compounds of the invention gave measurable damage to Echinochloa crus-galli at extremely low rates. Thus, the compound of Example 3 showed a 5% control of Echinochloa crus-galli at 0.035 kg / ha, and the compound of Example 5 showed a 10% control of Echinochloa crus-galli at 0.0175 kg / ha. The person skilled in the art can easily determine the optimum amount for each case, based on the description, including the examples. ·

so iiUkD 7

The term "soil" is used in the broadest sense of the word and includes all common soil types as defined under "soils" in Webster's New International Dictionary, Second Edition, Unabridged (1961). The term thus refers to any substance or medium in which plants can root and grow, and includes not only soil, but also compost, manure, dung, humus, sand and the like that can sustain plant growth.

End of the description

Claims (26)

Invention claim: A herbicidal preparation characterized by comprising an adjuvant and a herbicidally effective amount of a compound of formula I ClCH C (D includes, wherein R is allyl, chloroallyl, Pr.opargyl, 1-methoxyprop-2-yl or a Hydrocarbyloxymethylradikal of formula -CH ₀ OR ₁ represents wherein R, is allyl or a C ₁ alkyl radical. 2. Preparation according to item 1, characterized in that the compound of formula I is N-propargyl-2 '-ifbutoxy-6 "ethyl-2-chloroacetanilide. 3. Preparation according to item 1, characterized in that the compound of formula I is N- (1-methoxyprop-2-yl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 4. Preparation according to item 1, characterized in that the compound of formula I is N- (allyloxymethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 5. Preparation according to item 1, characterized in that in the compound, the formula IR _{1 is} a C ₃ _ ₅ alkyl radical • means. , -Jt- 6: preparation according to item 5, characterized in that the compound of formula I is N- (n-propoxymethyl) -2'-H butoxy-6'-ethyl-2-chloroacetanilide. 7. A preparation according to item 5, characterized in that the compound of the formula I is N - (sec-butoxymethyl) -2'-n-butoxy-6 ^l -ethyl-2-chloroacetanilide. 8. Preparation according to item 5, characterized in that the compound of formula I is N- (2-methylbutyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 9. Preparation according to item 5, characterized in that the compound of formula I is N- (isoamyloxymethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 10. A preparation according to item 5, characterized in that the compound of formula I is N- (isobutoxymethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 11. A preparation according to item 5, characterized in that the compound of formula I is N- (n-butoxymethyl) -2'-n-butoxy-6 ^1- ethyl-2-chloroacetanilide. 12. A method for controlling undesirable plants in crops, characterized in that at the location of these plants, a herbicidally effective amount of a compound of formula I is applied. 13. The method according to item 12, characterized in that the culture is planted rice. 14. A process according to item 13, characterized in that the compound of formula I is N-propargyl-2'-n-butoxy-6'-ethyl-2-chloroacetanilide, -So- 15. The method according to item 13, characterized in that the compound of formula I is N- (1-methoxyprop-2-yl) -2'- ; n-butoxy-6'-ethyl-2-chloroacetanilide. 16. The method according to item 13, characterized in that the compound of formula I is N- (allyloxymethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 17. The method according to item 13, characterized in that in the compound of formula IR _1, a C denotes alkyl radical. 18. The method according to item 17, characterized in that the compound of formula I is N- (n-propoxyrnethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 19. The method according to item 17, characterized in that the compound of formula I is N- (sec-butoxymethyl) -2'-n-butoxy-6 ^1- ethyl-2-chloroacetanilide. 20. The method according to item 17, characterized in that the compound of formula I is N- (2-methylbutyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 21. The method according to item 17, characterized in that the compound of formula I is N- (isoamyloxymethyl) -2'-n-butoxy-6 ^1- ethyl-2-chloroacetanilide. 22. The method according to item 17, characterized in that the compound of formula I is N- (isobutoxymethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 23. The method according to item 17, characterized in that the compound of formula I is N- (n-butoxymethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 24. The method according to item 12, characterized in that a herbicidally effective amount of Nr (allyloxymethyl) -2'-n-butoxy-6'-ethyl ~ -2-chloroacetanilide is applied for controlling weeds in planted rice at the site thereof. 25. The method according to item 12, characterized in that a herbicidally effective amount of N-propargyl-2'-n-butoxy-6'-ethyl-2-chloroacetanilide is applied for controlling weeds in planted rice at the site thereof. 26. A method according to item 12, characterized in that a herbicidally effective amount of N- (1-methoxyprop-2-yl) -2 "-n-butoxy-6'-ethyl is used in the control of weeds in planted rice at the site thereof. 2-chloroacetanilide is applied.