DK141202B - Thiadiazolylimidazolidinones with herbicidal activity. - Google Patents

Description

; “Τ · (11) PUBLICATION SHIFT 141202 DENMARK (B1) lnt 0.3 c 07 0 417/04 UMmviMmV A 01 N § 43/82 (21) Application No. 2580/74 (22) Filed on 9 * ®aJ 1974 (23) Running day 9 May 1974 (44) The application submitted and the thesis statement openend on 4. f eb. 1 98Ο

DIRECTORATE OF

PATENT AND TRADEMARKET SYSTEM (30) Priority requested

29 Jun. 1975, 375203, US

Jul 27 1973, 383417, US

Aug 13 1973, 388005, US

(7i) VELSICOL CHEMICAL CORPORATION, 341 East Ohio Street, Chicago, Illinois 130611, US.

I72) Inventor: John Krenzer, 435 North Elmwood, Oak Park, Illinois 6Ο3Ο2, US. "(74) Plenipotentiary in the proceedings:

The engineering firm Budde, Schou & Co ._____ (54) Thiadiazolylimidazolidinones with herbicidal action.

The present invention relates to novel herbicidal thiadiazolylimidazolidinones. The thiadiazolylimide azolidinones of the invention are peculiar in that they have the general formula

? H

N-N CH-CHO 1 1 I I I 2 (i)

R1 - C ft - N N - R

8 wherein R 1 is alkyl of 1-4 carbon atoms or trifluoromethyl, 2 and R is alkyl of 1-4 carbon atoms.

141202 2

From the disclosures of DK Patent Nos. 126,003, 128,782 and 130,001, it is known that certain 1,3,4-thiadiazolyl imidazolidinos have herbicidal activity.

Surprisingly, it has been found that the thiadiazolylimidazolidinones of formula (I) have a surprisingly good herbicidal activity over the known, closely related thiadiazolylimide azolidinones, as illustrated in more detail below.

The thiadiazolylimidazolidinones of the invention can be readily prepared by heating a compound of the formula

N-N

ill P

R - C C - N - C - N - CH0 - CH (II) \ fl / I II l2 2 i HOR AND? Wherein R and R have the meaning given above, in a dilute aqueous acidic reaction medium, for approx. 10 to approx. 60 minutes. Temperatures from approx. 0 ° C to the reflux temperature of the reaction mixture can be used. The reaction medium may contain a dilute aqueous inorganic acid, e.g. hydrochloric acid, at a concentration of approx. 0.5 to approx. $ 5 · After completion of the reaction, the desired product can be obtained as a precipitate by cooling the reaction mixture.

This product can be used as such or can be further purified by conventional means, e.g. recrystallization.

The compounds of formula II can be prepared by reacting one mole of isocyanate dimer of formula

N-N

0 = C = N-Ϊ C - R1 (III) J2 wherein R1 has the meaning given above, with approx. 2 moles of dimethyl metal of formula OCH, I 3 H - N - CH 2 - CH (IV)

l2 I

H OCH, 2 3 141202 wherein R has the meaning given above. This reaction may be carried out by heating a mixture of the feocyanate dimer and acetal in an inert organic reaction medium, e.g. benzene, at the reflux temperature of the reaction mixture. Reflux heating can be continued for approx. 2 to approx. 30 minutes to ensure complete circulation. Then, the desired product can be obtained by evaporation of the reaction medium and can be used as such or further purified by known methods.

The isocyanate dimer of formula III can be prepared by reacting a thiadlazole of the formula

N-N

in «1 R1 - C. C - m0 (V) N / wherein R1 has the meaning given above, with phosgene. This reaction can be carried out by adding a slurry or solution of the thiadiazole in a suitable organic solvent, e.g. ethyl acetate, for 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 ca. 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 present as a precipitate, or by evaporation of the organic solvent used if it is soluble therein. This product can be used as such or, if desired, further purified.

The process for preparing the compounds of the invention is further illustrated in the following Examples, in which Examples 1, 2, 4 and 5 illustrate the preparation of intermediates.

Example 1

Preparation of 5-trifluoromethyl-1,3,4-thiadlazol-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. Then, the reaction mixture is purified with nitrogen gas to remove unreacted phosgene.

141202 4

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-isoyanate dimer.

Example 2

preparation; of the dimethyllaetal of 2- / 1-methyl-3- (5-trifluoromethyl-1,5,4-thiadiazol-2-yl) ureido7acetaldehyde

A mixture of 9 * 5 g of 5-trifluoromethyl-1,3,4-thiadiazol-2-yl-isocyanate dimer, 5.8 g of dimethyl acetal of 2-methylaminoacetaldehyde and 60 ml of benzene is charged to a glass reaction vessel equipped with a mechanical stirrer and reflux. . The reaction mixture is heated under reflux in ea. 15 minutes. The benzene is then removed from the mixture by distillation under reduced pressure to give a solid product as residue. This product is recrystallized from heptane to give the desired product dimethyllaoetal of 2-T1-methyl-5- (5-trifluoromethyl-1,3 * 4-thiadiazol-2-yl) ureido7acetaldehyde, m.p. 101-102¾

Example 3

Preparation of 1- (5-trifluoromethyl-1,3 * 4-thiadiazol-2-yl) -3-methyl-5-hydroxy-1,3-imidazolidin-2-one 15 g 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 fitted with a mechanical stirrer, thermometer and reflux. The reaction mixture is heated at reflux for approx. 15 minutes. Then the reaction mixture is filtered while hot and the filtrate is cooled to form a precipitate product. The precipitated product is recovered by filtration, dried and recrystallized from a mixture of ethyl acetate and hexane to give the desired product 1- (5-trifluoromethyl-1,5,4-thiazolidin-2-yl) -3-methyl 5-hydroxy-1,5-imidazolidin-2-one, m.p.

156-158 ° C.

Example 4

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 into a glass reaction vessel equipped with a mechanical stirrer. A slurry of 10 g of 5-t-butyl-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.

Then, the reaction mixture is purified with nitrogen gas to remove unreacted phosgene. The purified mixture is then filtered to recover the desired product 5-t-butyl-1,3,4-thiadiazol-2-yl isocyanate dimer as a solid, m.p. 26L-263 ° C.

Example 5

Preparation of the dimethyl oetal of 2- [1-methyl-3- (5-t-butyl-1,3,4-thiadiazol-2-yl) ureido] oetaldehyde

A mixture of 6 g of 5-t-butyl-1,5,4-thiadiazol-2-yl-isocyanate dimer, 3.9 g of dimethyl acetal of 2-methylaminoacetaldehyde and 50 ml of benzene is charged to a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The reaction mixture is heated under reflux and stirring for approx. 5 minutes. The benzene is then removed from the reaction mixture by distillation to give an oil which solidifies on standing. The resulting solid is then recrystallized from pentane and the desired product is obtained from the dimethyl acetal of 2- [1-methyl-5- (5-t-butyl-1,3,4-thiadiazol-2-yl) ureido-7-ethyldehyde, m.p. 80-82 ° C.

Example 6

Preparation of 1- (5-t-butyl-1,3,4-thiadiazol-2-yl) -3-phenethyl-5-hydroxy-1,3-imidazolidin-2-one 16 g dimethyl acetal of 2- / 1 -Methyl-3- (5-t-butyl-1,3,4-thiazolidin-2-yl) ureido7acetaldehyde, 10 ml of concentrated hydrochloric acid 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 while hot and the filtrate is then cooled to form a precipitate product. The precipitated product is recovered by filtration, dried and recrystallized from a mixture of benzene and hexane to give the desired product 1- (5-t-butyl-1,3,4-thiadiazol-2-yl) -3-methyl 5-hydroxy-1,3-imidazolidin-2-one, m.p. 133-134 ° C.

141202 6

Example 7

Preparation of 1- (5-isopropyl-1,3,4-thiadiazol-2-yl) -3-methyl-5-hydroxy-1,3-imidazolidin-2-one 17 g of dimethyl acetal of 2- [1-methyl -3- (5-isopropyl-1,3,4-thiadiazol-2-yl) ureido] acetaldehyde, 10 ml of concentrated hydrochloric acid and 500 ml of water are charged into a glass reaction vessel equipped with a mechanical stirrer, a thermometer and a reflux condenser. The reaction mixture is heated at reflux for approx. 15 minutes. The reaction mixture is filtered while hot and the filtrate is then cooled to form a precipitate. The precipitate is filtered off, dried and recrystallized from a mixture of ethyl acetate and heptane to give the desired product 1- (5-isopropyl-1,3,4-thiadiazol-2-yl) -3-methyl-5- hydroxy-1,3-imidazolidin-2-one with m.p. 149-150 ° C.

Analysis for C 9 H 4 144 N 4 O 2 S: C Η N S

Calculated: 44.61 5.82 23.12 13.23

Found: 44.43 5.79 23.14 13.02

For practical use as herbicides, the compounds of this invention are incorporated with an inert carrier. Such herbicidal preparations allow the active compound to be easily applied to the weed-infested area in the desired amount. These compositions may be solids such as e.g. powders, granules, or moist powders, or they may be liquids, e.g. solutions, aerosols or emulsifiable concentrates.

For example, powders can be 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. Moisturizing powders which can be dispersed in water or oil to a desired concentration of the active compound can be prepared by incorporating wetting agents into concentrated powder formulations.

In some cases, the active compounds are sufficiently soluble in ordinary organic solvents such as e.g. petroleum or xylene so that they can be used directly as solutions in these solvents. Frequently, solutions of herbicides can be dispersed under over-atmospheric pressure as aerosols. However, preferred liquid 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 non-powdered 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 herbicidal composition is illustrated in the following example wherein the amounts are expressed in parts by weight.

Example 8

Preparation of a powder

Product of Example 6 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 compounds of the present invention in the herbicidal compositions varies greatly with the nature of the composition and the purpose for which it is intended, but usually the herbicidal compositions contain from about 20%. 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, nematocides, fungicides and the like, stabilizers, sprays, deactivators, adhesives, adhesives, fertilizers, activators and synergists.

141202 8

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. The novel compounds of this invention are particularly valuable for weed control 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 0.07-0.14 kg / ha of active compound may be sufficient for good control of a slight attack of weeds growing under adverse conditions, whereas it may be necessary to use 11.2 kg / ha or more active compound for good control of a dense attack of hardy perennial weeds growing under favorable conditions.

The herbicidal toxicity of the novel compounds of this invention has been demonstrated in experiments conducted for the pre-emergence control of many weed species. In these experiments small plastic herb pots filled with dry soil with weeds were sown. 24 hours or less after sowing, the pots are sprayed with water until the soil is wet and the test compounds formulated as aqueous emulsions of acetone solutions containing emulsifiers are 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 27 days, after which the condition of the plants and the degree of damage of the plants are determined on a scale of 0 to 10 as follows: 0 = not damaged, 1-2 = slightly damaged, 3-4 = moderately damaged, 5-6 = moderately severely damaged, 7-9 = severely damaged and 10 = dead.

The effectiveness of the compounds of this invention is shown in Table I.

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The herbicidal effect of the compounds of this invention has also been demonstrated in experiments performed for post-emergence control of many different weed species. In these experiments, the compounds of this invention are formulated as a solution in an inert solvent and sprayed at 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 degree of damage is determined 17 days after treatment and assessed on a scale of 0-10 as previously described. The effectiveness of the compounds is shown in Table II.

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As stated above, the thiadiazolylimidazolidinones of the invention have a surprisingly good herbicidal activity over the known thiadiazolylimidazolidinones, as illustrated in the following comparative experiment.

Test compounds QH

| H I I

N-N CH - CH, N- N CH-CH

If II I I 2 II II I I

F, C - C C - N N - CH, F, C - C C - N N - CH, 3 \ ^ \ / 3 3 \ 3 S C S ^ C- II Π o o A. B. (known)

Præémergensforsøg

Small plastic herb pots filled with dry soil were sown with weed seeds. Twenty-four hours after sowing, the pots are sprayed with water until the soil is wet and the test compounds formulated as aqueous emulsions are 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 14-28 days, after which the condition of the plants and the degree of damage of the plants are determined according to a scale of 0 to 10 as follows: 0 = not damaged, 1-2 = slightly damaged, 3-4 = moderately damaged, 5-6 = moderately severely damaged, 7-9 = severely damaged and 10 = dead. The results are shown in the following Table III.

Postemergensforsøg

The test compounds are formulated as a solution in an inert solvent and sprayed at 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 14-15 days after treatment and assessed on a scale of 0-10 as previously described. The results are shown in the following Table IV.

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OH

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CH, C

3 II

ISLAND

C.

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I I

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The results obtained are shown in Tables V and VI below.

141202 16

Table V

Postemergensforsøg

weed species

Number of da- Panicum Paspa- Fluminea

Experimental Quantity after crus Ipomo- Thalum di- Fox fox- Fly compound (kg / ha) application galli ea weed latatum tail cacea_hats 0.14 14 10 10 10 10 10 10 10 C 0.07 14 10 10 9 10 10 10 10 0.035 14 6 97 56 9 9 0.14 14 2 72013 2 D 0.07 14 0 7 1 0 0 0 1 0.035 14 0 30 00 0 3

Table VI

Præemergensforsøg

Number of da- Panicum Paspa- Fluminea

Experimental Quantity ge after crus Ipomo- Thalum di- Fox fox- Fly compound (kg / ha) application galli ea_weed latatum tail cacea_ oats 0.28 14 (22) 9 (10) 8 (10) 3 (10) 9 ( 10) 7 (10) 10 (10) 10 (10) C 0.14 14 (22) 9 (10) 5 (9) 3 (10) 4 (9) 7 (10) 10 (10) 9 (10) 0.07 14 (22) 4 (7) 5 (9) 1 (10) 3 (6) 3 (7) 8 (7) 6 (9) 0.28 14 (22) 7 (6) 0 (0) 0 (2) 5 (3) 2 (3) 0 (0) 1 (4) D 0.14 14 (22) 0 (1) 0 (0) 0 (1) 0 (0) 0 (0) 0 ( 0 (0) 0.07 14 (22) 0 (0) 0 (0) 0 (0) 0 (0) 0 (0) 0 (0) 0 (0)