DK144419B - 1-THIADIAZOLYL-5-ACYLOXYIMIDAZOLIDIONS WITH HERBICIDE EFFECT - Google Patents

Description

(W.

os) DENMARK \ Ra>

| J | 02) PRESENTATION WRITING (11) 144419 B

DIRECTORATE OF THE PATENT AND TRADEMARKET SYSTEM

(21) Application No. 5146/75 (51) Int.CI.3 C 07 D 417/04 (22) Filing Day 14. noV. 1975 J | N i3 / 82 (24) Race day l4. November 1975 (41) Aim. available Oct. 15 1976 (44) Submitted Mar 8 1982 (86) International application # - (86) International filing day - (85) Continuation day - (62) Master application no -

(30) Priority 14 Apr 1975, 567468, US 25 · Apr. 1975, 571466, US Apr 30 1975, 573188, US Jun 13 1975, 587006, US

(71) Applicant VELSICOL CHEMICAL CORPORATION, Chicago, US.

(72) Inventor John Krenzer, US.

(74) Associate Engineering Company Budde, Schou & Co.

(54) 1-Thiadiazolyl-5-acyloxyimidazole = idinones with herbicidal action.

The present invention relates to novel 1-thiadiazolyl-5-acyloxyimidazolidinones having herbicidal activity which are characterized in that they have the general formula q NN 0 - C - R 3 II / CH - CH 2 RX - CC - N / Tv m \ \ 2 (I)

Ώ Ns c-N - R

± 1 tf where R is alkyl or haloalkyl of 1-4 carbon atoms, t 3 R is alkyl of 1-4 carbon atoms, and R is alkyl of 1-8 carbon atoms or the group? (5-n)

-ISLAND

X

n where X represents alkoxy of 1-4 carbon atoms or halogen and n is an integer from 0 to 3.

Surprisingly, it has been found that the compounds of the present invention are useful as herbicides.

The compounds of this invention may be prepared by reacting a compound of the formula

OH

N-N I

1 I / CH —- 0¾ R1 - C b - Η I (II) XC-N - ΪΓ

II

wherein R and R have the above meanings, with an acid anhydride of the formula

P P

Wherein R · is as defined above in the presence of a catalytic amount of p-toluenesulfonic acid. This reaction can be effected by combining the reactants and the catalyst at room temperature in an inert organic reaction medium, whereupon the reaction mixture is heated under stirring on a steam bath for 1/2 to 4 hours. Thereafter, the reaction mixture can be cooled and the desired product recovered if formed as a precipitate product, or by evaporation of the organic reaction medium if it is soluble therein. In some cases, the acid anhydride can be used as a solvent for the compound of formula II, avoiding the use of an inert solvent as the reaction medium. When lower alkanoic anhydrides are used, water can be added to the reaction mixture to precipitate the desired product upon completion of the reaction.

3 144419

The product can then be purified in a conventional manner, e.g. by recrystallization. In some cases, the above reaction results in the formation of a mixture of products consisting of the desired compound and dehydrated starting material of the formula

N-N

II | / CH ^ = CH

R1 - c) - N (IV) -i2 r2 o 1 2 where R and R have the above meanings. In these cases, the desired product can be isolated by fractional precipitation.

The compounds of this invention may also be prepared by reacting a compound of formula II with an acid halide of formula 0

Cl - ϋ - R-5 (V) where T? has the aforementioned meaning, in the presence of an acid acceptor such as e.g. a tertiary amine. This preparation method can be used when the desired anhydride of formula III is not available. This reaction may be effected by slowly adding, under stirring, the acid chloride of Formula V to a solution of an approximately equimolar amount of the compound of Formula II in an inert solvent, in the presence of an acid acceptor at a temperature of ca. 10-30 ° C.

After the addition, the reaction mixture can be heated to a temperature up to the reflux temperature of the mixture to ensure completion of the reaction. The desired product may then be recovered by filtration of the reaction mixture to remove acid acceptor, followed by evaporation of the solvent if the product is soluble therein, or, if formed as a precipitate product, by filtration and subsequent washing and purification.

The compounds of Formula II can be readily prepared by heating a compound of Formula U4419 4 W-N no „, I II Γ3 R - C C - N - C - N - CH0 - CH VI)

\ s / I II l2 2 I

HOW AND

V

Wherein R and R have the above meanings, in a dilute aqueous acidic reaction medium, for approx. 10-60 minutes. Temperatures from approx. 70 ° C to the reflux temperature of the reaction mixture. The reaction medium may contain a dilute aqueous inorganic acid, e.g. hydrochloric acid, at a concentration of approx.

0.5 to approx. 5%. Upon completion of the reaction, the desired product can be recovered as a precipitating product by cooling the reaction mixture. This product can be used as such or can be further purified by conventional means, e.g. by recrystallization.

The compounds of formula VI can be prepared by reacting a molar amount of isocyanate dimer of formula

N-N

0 = C = N - C C-R1 ^ VI1 ^ - * 2 where R1 has the meaning given above, with approx. two molar amounts of dimethyl metal of formula OCH, in 5 H - N - CHO - CH (VIII) i2 2 in k OCH, p where R has the meaning given above. This reaction may be effected by heating a mixture of the isocyanate and acetal in an inert organic reaction medium such as e.g. benzene, at the reflux temperature of the reaction mixture. The reflux heating can be continued for approx. 2 to approx. 30 minutes to ensure complete turnover. Then, the desired product can be recovered by evaporation of the reaction medium and can be used as such or can be further purified in known manner.

5 U4A19

The isocyanate dimer of formula VII can be prepared by reacting a thiadiazole of formula

N-N

! II II (ix) R1 - C C - NH0 2 where R 1 has the above meaning, with phosgene. This reaction may be effected by the addition of a slurry or solution of the thiadiazole, in a suitable organic solvent, e.g. ethyl acetate, to a saturated solution of phosgene in an organic solvent such as e.g. ethyl acetate. The resulting mixture can be stirred at ambient temperature for from ea. 4 to approx. 24 hours. The reaction mixture can then be purified with nitrogen gas to remove unreacted phosgene. The desired product can then be recovered by filtration if it is formed as a precipitating product, or by evaporation of the organic solvent used if it is soluble therein. This product may be used as such or may be further purified.

As examples of suitable acid chlorides of formula V which can be used in the preparation of the compounds of the present invention may be mentioned the acid halides of the same acids mentioned under the examples of acid anhydrides.

The invention is further illustrated in the following Examples, Examples 1-3 and 5-7 relate to the preparation of starting materials and Examples 4 and 8 relate to the preparation of compounds of the invention.

Example 1

Preparation of 5-t-butyl-1,3,4-thiadiazol-2-yl isocyanate dimer

A saturated solution of phosgene in 100 ml of ethyl acetate is charged to a glass reaction flask equipped with a mechanical stirrer. A slurry of 10 g of 5-t-butyl-2-amino-1,5,4-thiadiazole in 300 ml of ethyl acetate is added to the reaction vessel, and the resulting mixture is stirred for approx. Then, the reaction mixture is purified with nitrogen gas to remove unreacted phosgene. The purified mixture is filtered to give the desired product 5-t-butyl-1,3,4-thiadiazol-2-yl isocyanate as a solid, m.p. 26L-263 ° C.

144419 6

Example 2

Preparation of the dimethyl acetal of 2- / 1-methyl-3- (5-t-butyl-1,3,4-thiadiazol-2-yl) ureido7acetaldehyde

A mixture of 6 g of 5-t-butyl-1,3,11-thiadiazol-2-yl isocyanate dimer, 3.9 S of the dimethyl acetal of 2-methylaminoacetaldehyde and 50 ml of benzene is charged into a glass reaction flask equipped with a mechanical stirrer. and reflux. The reaction mixture is heated under reflux and stirring for approx. 5 minutes. The benzene is then removed from the reaction mixture to give an oil which solidifies on standing. The resulting solid is recrystallized from pentane to give the desired product the dimethyl acetal of 2- / 1-methyl-3- (5-t-butyl-1,3,4-thiadiazol-2-yl) ureido7acetaldehyde, m.p. 80-82 ° C.

Example 5

Preparation of 1- (5-t-butyl-1,3 Ji <-thiadiazol-2-yl) -5-methyl-5-hydroxy-1,3-imidazolidin-2-one 16 g of the dimethyl acetal of 2- -Methyl-3- (5-t-butyl-1,3,3-thiadiazol-2-yl) ureido7acetaldehyde, 10 ml of concentrated hydrochloric acid and and 500 ml of water are charged to a glass reaction vessel fitted with a mechanical stirrer, thermometer and reflux. The reaction mixture is heated at reflux for approx. 15 minutes. The reaction mixture is filtered hot and the filtrate is then cooled to form a precipitate product. The precipitate product is recovered by filtration, dried and recrystallized from a mixture of benzene and hexane to give the desired product 1- (t-butyl-1- (1-thiadlazol-1-yl) -methyl-5-hydroxy-1 , 3-imidazolidin-2-one, m.p.

Example 4

Preparation of 1- (5-t-butyl-1,3'-thiadiazol-2-yl) -3-methyl-5-acetyloxy-1,3-imidazolidin-2-one 70 g of 1- (5-t butyl-1,3,4-thiadiazol-2-yl) -3-methyl-5-hydroxy-1,3-imidazolidin-2-one, 56 g of acetic anhydride and a catalytic amount of toluene sulfonic acid are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is heated on a steam bath with still stirring for approx. 2 hours. Then 500 ml of water is added to the reaction mixture to form a precipitate product. The precipitate is recovered by filtration and dried in an oven at 60 ° C. The dried product is recrystallized from ethanol and the desired product is obtained 1- (5-t-butyl-1,3,4-thiadiazol-2-yl) -3-methyl-5-acetyloxy-1,3-imidazolidin-2 -one with mp, 144 ° C.

Example 5

Preparation of 5-trifluoromethyl-1,3,4-thiadiazol-2-yl - isocyanate dimer

A saturated solution of phosgene in 100 ml of ethyl acetate is charged into a glass reaction vessel equipped with a mechanical stirrer. A slurry of 45 g of 5-trifluoromethyl-2-amino-1,3,4-thiadiazole in 300 ml of ethyl acetate is added to the reaction vessel and the resulting mixture is stirred for approx. 16 hours to form a precipitate product. The reaction mixture is then purified with nitrogen gas to remove unreacted phosgene. The purified mixture is filtered to obtain 48 g of white solid. This solid is recrystallized from dimethylformamide to give the desired product 5-trifluoromethyl-1,3,4-thiadiazol-2-yl isocyanate dimer.

Example 6

Preparation of the dimethyl acetal of 2- [1-methyl-3- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) ureido] acetaldehyde

A mixture of 9.5 g of 5-trifluoromethyl-1,3,4-thiadiazol-2-yl-isocyanate dimer, 5 * 8 g of the dimethyl acetal of 2-methylaminoacet aldehyde and 60 ml of benzene is charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The reaction mixture is heated at reflux for approx. 15 minutes. The benzene is then removed from the mixture under reduced pressure and a solid product is obtained as residue. This product is recrystallized from heptane and the desired product is obtained from the dimethyl acetal of 2- / 1-methyl-3- (5-trifluoromethyl-1,3 * 4-thiadiazol-2-yl) ureido7-acetaldehyde, m.p. 101-102 ° C.

144419 8

Example 7

Preparation of 1- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) -5-methyl-5-hydroxy-1,3-imidazolidin-2-one 15 g of the dimethyl acetal of 2- / 1-methyl 3- (5-Trifluoromethyl-1,3,4-thiadiazol-2-yl) ureido7acetaldehyde, 400 ml of water and 4 ml of hydrochloric acid are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux. The reaction mixture is heated at reflux for approx. 15 minutes. The reaction mixture is then filtered hot and the filtrate is cooled to form a precipitate product. The precipitate product is recovered by filtration, dried and recrystallized from a mixture of ethyl acetate and hexane to give the desired product 1- (5-trifluoromethyl-1,3,1-f-thiadiazol-2-yl) -3-methyl 5-hydroxy-1,3-imidazolidin-2-one, m.p. 136-138 ° C.

Example 8

Preparation of 1- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) -3-methyl-5-acetyloxy-1,3-islamidazolidin-2-one 0.05 mole of 1- (5-trifluoromethyl) -1,3Λ-Thiadiazol-2-yl) -3-methyl-5-hydroxy-1,3-imidazolidin-2-one, 6 ml of acetic anhydride, 20 ml of acetic acid and 0.1 g of toluene sulfonic acid are charged to a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is stirred at room temperature for approx. 24 hours. Then 200 ml of water is added to the reaction mixture. The resulting mixture is extracted with ether and the ether extract is washed with aqueous sodium carbonate and dried over anhydrous magnesium sulfate. The dried solution is then filtered and the solvent removed under reduced pressure to give a solid residue. This solid residue is recrystallized from a mixture of water and methanol to give the desired product 1- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl) -3-methyl-5-acetyloxy-1.3 -imidazolidin-2-one as a crystalline solid, m.p. ^ 72-7 ° C.

144419 9

For practical use as herbicides, the compounds of this invention are usually incorporated into herbicidal agents containing an inert carrier and a herbicidal toxic amount of such compound. Such herbicidal agents, which may also be called preparations, cause the active compound to be readily applied to the weed infected area in the desired amount. These materials may be solids such as e.g. powders, granules, or moist powders, or they may be liquids, e.g. solutions, aerosols or emulsifiable concentrates.

Powders can e.g. is prepared by grinding and mixing the active compound with a solid inert carrier such as e.g. talc, clay, silica or pyrophyllite. Granule preparations can be prepared by impregnating the compound, usually dissolved in a suitable solvent, on and in granulated carrier materials such as e.g. attapul grids or vermiculites, usually in the particle size range from about. 0.3 to 1.5 mm. Moisture powders which can be dispersed in water or oil to a desired concentration of the active compound can be prepared by incorporating wetting agents in concentrated powder formulations.

In some cases, the active compounds are sufficiently soluble in ordinary organic solvents such as e.g. petroleum or zylene so that they can be used directly as solutions in these solvents. Often solutions of herbicides can be dispersed under over-atmospheric pressure such as aerosols. However, preferred liquid herbicidal compositions are emulsifiable concentrates which contain an active compound of the present invention and as inert carrier a solvent and an emulsifier. Such emulsifiable concentrates can be diluted with water and / or oil to a desired concentration of active compound for application as a spraying agent in the weed-infested area. The emulsifiers commonly used in these concentrates are nonionic or mixtures of nonionic with anionic surfactants. By using some emulsifier systems, an inverted emulsion (water in oil) can be prepared for direct application to weed-infested areas.

A typical agent containing a herbicidal compound of the present invention is shown in the following examples wherein the amounts are given in parts by weight.

144419 10

Example 9

Preparation of a Powder Product of Example 4 10

Talc 90

The above ingredients are mixed in a mechanical grinding mixer and ground until a homogeneous, free-flowing powder of the desired particle size is obtained. This powder is suitable for direct application to the weed-infested area.

The compounds of this invention can be applied as herbicides according to all known methods. One method of weed control is to contact the weed site with herbicidal compositions containing an inert carrier and, as an essential active ingredient in an amount that is herbicidal toxic to the weed, a compound of the invention. The concentration of the novel compounds of this invention in the herbicidal preparations varies greatly with the nature of the preparation and the purpose for which it is intended, but usually contains the herbicidal preparations from about 10%. 0.05 to approx. 95% by weight of the active compounds herein. In a preferred embodiment of the present invention, the herbicidal compositions contain from ca. 5 to approx. 75% by weight of active compound. The compositions may also contain such additional substances as other pesticides such as e.g. insecticides, nematodicides, fungicides, stabilizers, sprays, deactivators, adhesives, adhesives, fertilizers, activators, synergists.

The compounds of this invention may also be used in combination with other herbicides and / or defoliation agents, dessicants or growth inhibitors in the herbicidal compositions described above.

These other materials may contain from ca. 9% to approx. $ 95 active ingredients in the herbicidal preparations. By using combinations of these other herbicides and / or defoliation agents, dessicants etc. with the compounds of the present invention, herbicidal preparations are provided which are more effective in controlling weeds and often yield results which are unattainable with separate preparations of the individual herbicides.

11 U4419

Weeds are undesirable plants that grow in undesirable places, without economic value, and which interfere with the production of cultural crops, the cultivation of ornamental plants or the welfare of the livestock stock. Many weed species are known, including annual plants such as Kvinoa, Chenopodium album, Fox tail, Digitaria sarguina-lis, Sinapis arvensis, Thlaspi arvense, ryegrass, Eleusine indica, Stellaria sp., Avena fatua, velvet leaf, portulak, Echinochloa, Persi-carla hydropiper, Polygonum aviculare , Medicago, KLinte, Ambrosia, pig milk, Cassia marylandica, croton, Cuphea, Cuscuta, Fumaria, Senecio vulgaris, Galeopsis, Scleranthus, warthog, Spergula arvensis, emex, Echinochloa colonum, Potamogeton, Galgo, Anthemis cotula, Anthemis cotula, Anthemis cotula , Naias, back herons, autumn millet, Datura stramonium, mercury, Panicum virgatum, Paspalum dilatatum, teaweed, wild turnips and Flurainea festueacea, biennial plants such as wild carrot, Matricaria, wild barley, Lychnis, Anthemis, Arctium, Verbascum, round-leafed cotton, horsetail, dog tongue, Verbascum blattaria and purple bud, or perennial plants, such as white clump, perennial ryegrass, mercury, Sorghum tail brush, field thistle, Convolvulus sepium, Bermuda grass, red knee, rippled debris,

Cyprus sp., Cerastium arvense, dandelion, Campanula, Convolvulus arvensis, Centaurea picris, Propopis, Linaria, Achillea millefolium, Aster, Lithospermum, Equisetum, Vernonina, Sesbania, Scirpus, downhammer, winter karse, Solanum carolinense, Cyperus

Such weed species may also be classified as broadleaf or grass weed species. It is economically desirable to control the growth of such weeds without damaging the crops or livestock.

The compounds of this invention are particularly valuable for the control of weeds as they are toxic to many species and groups of weeds, whereas they are relatively non-toxic to many utility plants. The exact amount of compound needed depends on many different factors, such as the hardness of the particular weeds, the weather, the soil, the method of application and the nature of the crops in the same area. Thus, the use of up to only approx.

U4A19 12 0.07-0.14 kg / ha active compound may be sufficient to effectively control a slight attack of weeds growing under adverse conditions, whereas 11.2 kg / ha or more active compound may be required to good fight against a dense attack of hardy perennial weeds growing under favorable conditions.

The herbicidal toxicity of the novel compounds of this invention can be illustrated by many of the recognized test methods known in the art, such as e.g. pre- and post-emergence trials.

The herbicidal activity of the compounds of this invention has been demonstrated by experiments conducted to pre-emergence control of many weed species. In these experiments, small plastic herb pots filled with dry soil were seeded with the various weed seeds. 24 hours or less after sowing, the pots are sprayed with water until the soil is wet and the test compound formulated as an aqueous emulsion of an acetone solution containing emulsifiers is sprayed at the indicated concentrations on the soil surface.

After spraying, the herb pots are placed in the greenhouse and additional heat is added as needed and daily or more frequent watering. The plants remain under these conditions for approx. 15-21 days, after which the condition of the plants and the degree of damage of the plants are determined on a scale from 0 to 10 as follows: 0 = not damaged, 1-2 = slightly damaged, = moderately damaged, 5-6 moderately severe, 7-9 = severely damaged and 10 dead. The effectiveness of the compounds of this invention is shown in the following Table I.

144419 13

Table I

damage Assessment

Product according to Example 4 Concentration (kg / ha)

Weed Species 4,48_1,12_0.28

Cyprus 10 8 5

Flying Oats 10 10 9

Datura stramonium 998

Velvet leaf 10 10 9

Sorghum tail pens 10 10 10

Kvinoa 10 10 10

Sinapis 10 10 10 Fox Tail

Panicum erus bile 10 10 10

Digitaria 10 10 10

Returns 10 10 10

Ipomoea 10 10 10

Further results from pre-emergent trials for herbicidal activity made with the compounds of this invention are shown in the following Table II. In these tests, damage assessment was performed for each compound, respectively. 14 days and 21 days after treatment 14 UU19 in — 1!

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The herbicidal effect of the compounds of this invention has also been demonstrated by experiments carried out for post-emergence control of many different weed species. During these tests, the test compounds are formulated as an aqueous emulsion and sprayed in the indicated dose on the leaves of the weeds which have reached the prescribed size. After spraying, the plants are placed in a greenhouse and watered daily or more often. No water is poured onto the leaves of the treated plants. The rate of damage is determined 10-15 days after treatment and assessed on a scale of 0-10 as described above. The effectiveness of the compounds is shown in Table III.

Table III

damage Assessment

Product according to Example 4 Concentration (kg / ha)

Weed Species 4,48_1,12_0.28

Cyprus 10 10 4

Flying Oats 10 10 10

Datura stramonium 10 10 10

Kvinoa 10 10 10

Sorghum tail brushes 10- 10 10

Snerle 10 9 10 S inapis 10 10 10 Foxes · 10 10 10

Panicum crus galli 10 10 10

Digitaria 10 10 10

Ipomoea 10 10 10

Further results from post-emergent trials for herbicidal activity made with the compounds of this invention are set forth in the following Table IV. In these trials, damage assessment was performed for each compound 14 days after treatment.

27 144419

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144419 33

In order to compare the herbicidal activity of the compounds of this invention with known compounds, pre-emergent experiments are performed as described above. The test compounds are formulated in an inert solvent. Damage assessment is performed, respectively. 14 days and 21 days after treatment. The results are shown in the following table V.

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Similarly, post-emergent experiments are performed as described above. The test compounds are formulated in an inert solvent. Damage assessment is done 14 days after treatment. The results are shown in the following Table VI.

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