DE1921840A1 - Herbicides - Google Patents

Description

CIBA AKTIENGESELLSCHAFT, BASEL (S CH WE IZ)

Case 6458 / E

Herbicidal agents

The present invention relates to agents for controlling
of unwanted plant growth acting as an active substance
at least one compound of the general formula

^ -NIF-CO-R ₂ (I)

contain, in which R, a lower alkenyl or alkynyl radical or an optionally substituted phenyl radical, X represents oxygen or sulfur and R represents an aliphatic _} cycloaIiphatic or heterocyclic radical, together with at least one of the following additives:

909947/1203

Carriers, solvents, diluents, dispersants, emulsifiers, wetting agents, adhesives, thickeners and / or other pesticides especially herbicidal, or fertilizers.

Compounds of the formula are predominantly used as active substances

NH-GOR ₄ (II)

in question, in which R is an alkenyl or alkynyl radical with 2 to 4 Carbon atoms and one with -F, -Cl, -Br, -J, -NO, -CN,

-CF ,, -CF Cl, 1-4 alkyl groups is substituted phenyl, X is oxygen or sulfur and R ^ is an alkyl, haloalkyl, cyanoalkyl, rhodanoalkyl, ^, nitroalkyl, isocyanatoalkyl, isothiocyanatoalkyl, Denotes carboxyalkyl, carbalkoxyalkyl, carboxamidoalkyl groups whose branched or unbranched alkyl chains have 1 to 18, preferably 1 to 10, carbon atoms and can be substituted and Ru denotes an alkenyl, carboxyalkenyl, carbalkoxyalkenyl, carboxyamidoalkenyl, alkynyl, haloalkynyl group, whose alkenyl or alkynyl chains have 2 to 4 carbon atoms and R _{1 is} a substituted or unsubstituted cycloalkyl radical with 3 to 6 ring members and 5- or 6-membered heterocycles.

Herbicidal compositions have proven to be particularly effective which, as active substances, contain compounds of the formula

. ..; ORIGINAL INSPECTiD

909847 / 12U3

19? ¹ BAQ

(in)

contain, where η is 0, 1, 2 or 3 and R_ is a corresponding one

L?

Number of independent substituents such as halogen, C ₁ -C 4 alkyl, C 1 -C 4 -AlkOXy, C- ^ C ^ -haloalkyl, trifluorinethyl, difluorochloromethyl, dichlorofluoromethyl, trichloromethyl, nitro, nitrilo, rhodano and TU and X as defined above sirri,

The following are examples of compounds suitable for the purposes of the invention.

BATH 9 09847/1203

CF.

CO — R,

Cl-

CH ₂ = CH-CH ₂ -

HC = C -

CH,

-C.

-O.

-O ₂ H ₅

-O ₂ H ₅

-σ.

: ^H 5

9098 A 7/1

O O

The active substances of the formula (i) are selective Effects against various weeds, especially those in cereal, soybean, carrot and maize crops, while the crops are spared. But under weeds also understood undesirable, e.g. previously cultivated plants. With a sufficiently large application rate, however, it is also total herbicidal Effect present. The active ingredients can be used both pre-emergence and post-emergence. Included the application rate can vary within wide limits, e.g. between 0.1 to 10 kg of active ingredient per hectare, but preferably 0.5 to 5 kg of active ingredient per hectare. The above - defined Compounds are also suitable as active ingredients for exerting other inhibitory effects on plant growth in particular defoliation of e.g. cotton plants, acceleration of ripening due to premature drying out e.g. potato plants furthermore also reduction of the fruit set, delay of flowering, extension of the harvest period and improvement of the Shelf life of harvested products. Also, the use of growth-inhibiting agents may not only be due to the Suppression of the weeds lead to an increase in yield, but also by the fact that this means counteracts influences acts »which causes the growth of crops in undesirable Direction could stimulate, such as high temperatures or abundant fertilization. On the other hand, the use of herbicidal Means of eradicating stubborn weeds in the long run may also be of interest if the selectivity of the agent is concerned not sufficient to exclude a reduction in the yield of the plants grown at the time of application «

ORIGINAL IMSPECTED

The new agents can be used in a variety of ways. Aqueous sprays can for example be based on an emulsifiable concentrate or a wettable powder be generated. A suitable emulsifiable concentrate can for example from about 25 parts of a compound of formula (i) or (il) 40-50 parts of diacetone alcohol or isophorone, 20-30 parts of an aromatic petroleum product, xylene, toluene or other mixture of such solvents, and 2-10 parts of one or more emulsifying agents can be prepared. There can also be small amounts of an agent that the training. a homogeneous solution such as methanol, ethoxymethanol or butoxymethanol can be used.

A suitable emulsifying agent may, for example, consist of 1-1.5 parts of calcium dodecylbenzenesulphonic acid or 2.5 parts of sodium an octyl- or nonyl-phenoxy-polyethoxyethanol and approximately 0.5-1 part of methanol and 0-0.8 parts of xylene are prepared. The resulting mixture is the solvents and the active body of formula (i) or (il) in that given above Quantity ratio added. However, one or more other surfactants can also be used.

A wettable powder can be obtained when taking an active compound of general formula (I) or (II) in a volatile solvent such as acetone and treated with a finely divided solid, such as kaolin ,, pyrophyllite, or diatomaceous earth, with evaporation of the solvent _β matches the Powder is heated with small amounts of one or more wetting agents and ■ dispersants. A typical composition consists, for example, of 20 parts of an active ingredient, 5 parts of an or

ORIGINAL INSPECTED

- 1 -

19 ° ι 8 4 O

several finely divided solids, 0.5 parts of a wetting agent such as an octyl-phenoxy-polyethoxyethanol and 2 parts of the sodium salt of a condensed naphthalene formaldehyde sulfonate.

Dusts with an active ingredient content of $ 5-10 can be prepared by diluting such a wettable powder with a finely divided solid support. If desired, the wetting agent and the dispersing agent can be omitted or replaced by others.

In some cases, granules are beneficial. They can be made by dissolving the active ingredient in an organic solvent, absorption of this solution by granulated mineral, e.g. Attapulgite or SiO followed by removal of the solvent produce.

Each of the herbicidal preparations described above usually contains a carrier and in most cases a surface-active one Middle.

Further information on application technology can be found in U.S. Patent 3,329,702 or Brit. Patent 1, θ4γ, 644 or Swiss patent 424,359.

In the preparation of the herbicidally active agents can For example, the following components can also be used in combination:

N-phenyl-N '^ - dimethyl urea, N- (3-chloro-4-methoxyphenylJ-NSN'-dimethylurea, Np-chlorophenyl-N ¹ , N'-dimethylurea, N-3,4-dichlorophenyl-N ^l , N ^t -dimethylurea, N-3,4-dichlorophenyl-N'-methoxy-N'-methylurea, N-4-bromo-3-chloropheriyl-N'-methoxy-N'-methylurea, Neburon, Cotoran, Maloran, trichloro

acetic acid, 2,6-dichlorobenzonitrile, bromoxynil, joxynil, 2,3 * 6- _w , _ ⁹ 098 ^ _{7/1 203 OR! Ö1NAL mS} PECTEi>

- 8 - 19? ¹ 840

Trichlorobenzoic acid, 2,4-D, 2,4-T, MCPB, MCPP, isopropyl carbanilate ,. Isopropyl-3-chlorocarbanilate, N - ^ - chlorophenylcarbamic acid- ^ 'chlorobutin-2-yl-1-ester, ordram, 2,3,6-trichlorophenylacetic acid and salts, 3. »^ - dichloropropionanilide, 2-chloro-diallylacetamide , 2-chloro-4 _i 6-bis-ethylamino-s-triazine, 2-azido-4-methyl-thio-6-isopropylaminotriazine, 4-ethylamino-2-tert. butylamino-6-methylthios-triazine, CCC preparations, 3i6-dichloro-2-πlethoxybenzoic acid, 2,3 ^ 6-trichlorobenzoic acid, barban, triallates, dinitrocresols and other dinitro derivatives, monomethylarseniate di-Na salt, various Arsenite, sodium metaborate, sodium chlorate, sulfamic acid.

The anilides of the formula (i) are new. The invention also refers to these new connections.

They can be obtained by known processes for the preparation of acid anilides, for example by adding an aniline of the formula

with a corresponding carboxylic acid which has the substituent for the desired active ingredient of the general formula (i). R _{p is to} form, converts, or with a carboxylic acid halide, anhydride or ester derived therefrom. But you can also use an isocyanate of the formula

R ₁ -X-

IfCO

Allow to react with a corresponding carboxylic acid with GO _{2 separation.} The substituents R ₁ , R ₂ and X have the

for-Pormel ... (Il given meaning. " _ΙΛ4ΚΙΔ ϊ

«*.""*. 9 0 9 8 47/1203 original

example 1

A three-necked sulphurizing flask equipped with a stirrer, thermometer and two dropping funnels was initially charged: 41.4 g of 4-methoxy-3-trifluoromethylaniline and 300 ml of benzene. At an internal temperature of 10 ° -30 ° C., 18 g of pyridine and 20 g of propionic acid chloride, dissolved in 25 ml of benzene each time, were added dropwise at the same time. The mixture was then stirred at room temperature for 2 hours. The reaction product was washed once with 100 ml of 2N HCl and 3 times with 100 ml of water, dried over sodium sulfate and the benzene was distilled off. The crude product obtained was finally recrystallized from acetone / water. This gave 46.3 B * that is 93.8% of theory, propionic acid - ^ - methoxy ^ -trifluoromethylanilide with a melting point of 105 ° -109 °. [Compound No. 2]

In an analogous manner, the following compounds of the formula

R ₇

manufactured*

OBIÖIWAL

90 9I4 U 1203

19-1840

Verbg. No.

10

-SGH.

CF,

Cl

Cl

Cl

Cl-

Cl

H-

CH,

-GH = CH ₀

GEL

-OF-

O-

M.p. G

70-78

OeI

OeI

134-137

101-104 55-58 Oei

97-100 113-115

OeI

INSPECTED

309847/1303

1971840

Connection no.

M.p. ⁰ C

11 12

14th

15th

16

17th

18 19

20th

<f> -σι

Cl

-CH ^ -CH = CH.

Cl

CH

CH.

C 0

> ^Η 5

-O ₂ H ₅

-O ₂ H ₅

-O ₂ Hg

-0_Η _κ

73-74

79-81

95-100

50-52

65-68

88-90

OeI

110-118

ScJp.

160-188

909847/1203

1971840

Example 2

a) 50 g of active ingredient, and 40 g of bolus alba with 5 g of Zeosil and finely grind 5 g dispersants. So you get a 50 # wettable powder that can be diluted with water as required.

b) There were 40 parts of compound no. 7 with 25 parts of a mixture of an anionic surface-active compound, preferably the calcium or magnesium salt of monolaurylbenzene monosulfonic acid, and a nonionic surface-active Compound ^ preferably a polyethylene glycol ether of the monolauryl ester of sorbic acid, mixed and diluted to 100 ecm with xylene. A clear solution is obtained emulsified by adding water and used as a spray concentrate can be used.

! NSPECTED

909847/1203

Example 3

In the greenhouse the following types of plants were grown for a Later post-emergence treatment sown:

Triticum, Hordeum, Avena, Zea May, Oryzä, Gossypium, Digitaria, Sorghum, Beta, Calendula, Chrysanthemum, Brassica, Ipomoea, Stellaria, Amaranthus.

Depending on the type of plant, 12-14 days after sowing with an application rate of 1-2 kg of the compounds No. 7 in In the form of a wettable powder, the above-mentioned plants are sprayed in the 2-leaf stage. Twenty days after the Treatment was evaluated. The results are summarized in the following table:

Plant species Post-emergent - - ■ - - - ■ No.
andmengi
2kg Verb.]
12th
lkg Wr.
2kg Verb.
14th
lkg No.
2kg Verb.
11th
Exp
lkg - 9 1 1 2 2 3 Triticum 1 9 6th 1 1 2 1 2 Hordeum 1 9 6th - - - - - Avena 9 - - - 1 1 Zea Mays - 2 3 - - Oryza - - - 1 1 Gossypiura - 5 9 - Sorghum 9 8th 9 - - Digitaria 9 9 9 9 9 beta - 9 9 ■ - - - Calendula * - 9 9 - - Chrysanthemum 9 9 9 8th 8th Brassica 8th 9 9 - - Ipomoea 7th 9 9 8th Stellaria 9 9 9 9 9 Amaranthus

Evaluation: 1-3 = plants not or hardly affected

4-6 = Medium damage

7-8 = severe damage

9 = plants dead

Claims (1)

Claims 1. Herbicidal agents which are a compound as the active substance the formula NH-CO-R contain, wherein R, a lower alkenyl or alkynyl radical or denotes an optionally substituted phenyl radical, X denotes oxygen or sulfur and R denotes an aliphatic, cycloaliphatic or heterocyclic radical, together with at least one of the following additives: carriers, solvents, Diluents, dispersants, emulsifiers, wetting agents, adhesives, thickeners and / or other pesticides in particular herbicidal kind, or fertilizers. 2 ... Herbicidal agents according to claim 1, which are used as active Substance a compound of the formula NH-COR ₄ contain, in which R, an alkenyl or alkynyl radical with 2 to '4 Carbon atoms and a phenyl radical substituted with -F, -Cl, -Br, -J, -NOp, -CN, -CF. ,, -CFpCl, 1-4 alkyl groups, X stands for oxygen or sulfur and R, an alkyl, haloalkyl, Cyanoalkyl, rhodanoalkyl, nitroalkyl, isocyanatoalkyl, Isothiocyanatoalkyl, carboxyalkyl, carbalkoxyalkyl, carboxamidoalkyl group means their branched or unbranched alkyl chains 1 to 18, preferably 1 to 10, carbon atoms. and can be substituted and R ^ is an alkenyl, carboxyalkenyl, 909847/1203 ORlQWAL INSPECTED ^ Carbalkoxyalkenyl., Carboxamidoalkenyl, carbalkoxyalkenyl, carboxamidoalkenyl, alkynyl, haloalkenyl groups whose alkenyl or alkynyl chains have 2 to 4 carbon atoms and Ru is a substituted or unsubstituted cycloalkyl radical with 3 to 6 ring members and 5-. or mean 6-membered heterocycles. 3. Herbicidal agents according to claim 2, which as active Substance a compound of the formula ■ NH — CO — R where η is 0, 1, 2 or 3 and R ^ is a corresponding number of mutually independent substituents such as halogen, C ₁ -C ₂ , alkyl, C ₁ -C ^ -AIkOXy, C ₁ -C ₂ ^ haloalkyl, trifluoromethyl , Difluorochloromethyl, dichlorofluoromethyl, trichloromethyl, nitro, nitrilo, rhodano and R ₂ and X have the meaning given in claim 2. · 4. Herbicidal agent according to claim 3, which is the compound of the formula NH-CüC _o H _c c. 0 Contains JNSPECTSD. 09847/120 3 ft 5. Herbicidal agent according to claim 3, which as active substance the compound of formula -NH-COC ₅ H ₁ - 2 D contains. 6. Herbicidal agent according to claim 3, which is the compound of the formula C ₀ ILO-CH ₀ -CH ₀ - d 0 dd - co-C contains. 7 · Herbicidal agent according to claim 3, which is available as active substance the compound of formula _(X > -NH-COC ₂ H ₅ contains. ' 8. Use of an agent according to claim 1 for combating of weeds in monocotyledon and dicotyledon crops. 909847/1203 ORIGWAL WSPECTtD 9 · Use according to claim 8 of an agent according to Claim 1 for combating weeds in grain and cotton .. 10. Use according to claim 9 of an agent according to claim 1 for combating weeds in wheat, maize, Barley, oats and rice. ■ "11J Process for the preparation of the active ingredient in the Means according to claim 1 used compounds of the formula wherein R, a lower alkenyl, alkynyl radical or an optionally substituted phenyl radical, X stands for oxygen or fc sulfur and Rp an aliphatic, cycloaliphatic or represents heterocyclic group by adding an aniline of the formula with an appropriate carboxylic acid to form the substituents Rp for the desired active compound of the general formula, are reacted, or ester with a carboxylic acid halide derived therefrom, anhydride, or _T. But you can also use an isocyanate of the formula ■■■ * ^! "" · ■ --- '~ - ■ -. 908847/1203: ORIGHNAL INSPECTED 19 ^ 1840 rait a corresponding carboxylic acid with CO separation let react. 12. Anilides , which are encompassed by the formula in claim 1. 13. Anilidej which of the formula in claim 2 includes will. 14. Anilides, which are covered by the formula in claim 3 will. 15. Anilide, the formula in claim 16. Anilide of the formula in claim 17. Anilide of the formula in claim 18. Anilide, the formula in claim 0 9847/1203 ORISiNAL IMSPBCTSD