JPS5852964B2 - Japanese porridge - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel compositions of matter and more particularly relates to novel compositions of matter of the formula ~7 cycloalkyl, and R2 is alkyl.

).

The compounds of this invention are unexpectedly useful as herbicides.

In a preferred embodiment of the invention, R1 is lower alkyl, lower alkoxy, cycloalkyl of 3 to 7 carbon atoms optionally substituted with chlorine or bromine, and R2 is lower alkyl.

As used herein, the term "lower" refers to straight or branched carbon chains of up to 6 carbon atoms.

The compound formula of the present invention is the formula (In the formula, R1 and R2 have the same meanings as above.

) in a dilute aqueous acidic reaction medium for about 10 to 60 minutes.

Temperatures from about 70° C. to the reflux temperature of the reaction mixture can be used.

The reaction medium can contain a dilute aqueous inorganic acid, such as hydrochloric acid, at a concentration of about 0.5-5%.

After the reaction is complete, the desired product is obtained as a precipitate by cooling the reaction mixture.

This product can be used as is or can be further purified by conventional means such as recrystallization.

The compound of formula ■ is 1 molar amount of the formula (In the formula, R1 has the same meaning as above.

) is the isocyanate dimer represented by the formula (In the formula, R2 has the same meaning as above.

) can be produced by reacting with dimethyl acecool represented by

This reaction can be accomplished by heating the mixture of isocyanate dimer and acecool in an inert organic reaction medium such as benzene to the reflux temperature of the reaction mixture.

Heating under reflux is continued for about 2 to 30 minutes to ensure completion of the reaction.

The reaction medium is then evaporated to obtain the desired product.

This product can be used as is or can be further purified by standard methods in the field.

The isocyanate dimer represented by the formula ■ has the formula (in the formula,
R1 has the same meaning as above.

) can be produced by reacting thiadiazole represented by phosgene with phosgene.

This reaction can be accomplished by adding a slurry or solution of Chadiazole dispersed or dissolved in a suitable organic solvent such as ethyl acetate to a saturated solution of phosgene dissolved in an organic solvent such as ethyl acetate.

The resulting mixture can be stirred at ambient temperature for about 4 to 24 hours.

The reaction mixture can then be flushed with nitrogen gas to remove unreacted phosgene.

The desired product can then be obtained by filtration if it forms as a precipitate or by evaporating the organic solvent if it is in solution.

This product can be used as is or can be further purified if desired.

Representative thiadiazoles of formula (1) useful in preparing the compounds of this invention include 5-cyclopropyl-2-
Amino-1,3,4-thiadiazole, 5-cyclobutyl-2-amino-1,3゜4-thiadiazole, 5-cyclopentyl-2-amino-1,3,4-thiadiazole, 5-cyclohexyl-2-amino-1 ,3,4-thiadiazole,5-cyclohebutyl-2-amino-1,3
゜4-thiadiazole, 5-(2methylcyclobutyl)
-2-amino-1,3,4-thiadiazole, 5-(3
-methoxycyclopentyl)-2-amino-1,3,4
-thiadiazole, 5-(3-chlorocyclohexyl)
-2-amino-1,3,4thiadiazole, 5-(1-
methylcyclohexyl)-2-amino-1,3,4-thiadiazole, 5-(4-hydroxycyclohexyl)
-2amino-1,3,4-thiadiazole, 5(4-1
0-lycyclohexyl)-2-amino-1゜3.4-thiadiazole, 5-(4-bromocyclohexyl)-2-
Amino-1,3,4-thiadiazole, 5-(3-ethylcycloheptyl)2-amino-1,3,4-thiadiazole, 5(3-propoxycyclohexyl)-2-amino1,3,4-thiadiazole, etc. It is.

The method for preparing the compounds of the invention is explained in more detail in the Examples below.

Example 1 5-cyclopropyl-1,3,4-thiadiazole-2
-Production of isocyanate dimer Ethyl acetate (100
A saturated solution of phosgene dissolved in mA was charged to a glass reactor equipped with a mechanical stirrer.

A slurry of 5-cyclopropyl-2-amino-1,3,4-thiadiazole (6 g) in ethyl acetate (100 m) was added to the reactor, and the resulting reaction mixture was
When the mixture was stirred for an hour, a precipitate was formed.

Then, nitrogen gas was blown into the reaction mixture to remove unreacted phosgene.

The desired product, 5-cyclopropyl-1,3,4-thiadiazole-, is obtained by filtering the blown mixture.
A 2-yl isocyanate dimer was obtained.

Example 2 2-[1-methyl-3-(5-cyclopropyl 1.3,
Preparation of dimethylacecool from 4-thiadiazol-2-yl)ureido]acetaldehyde 5-cyclopropyl-1,3,4-thiadiazole-2
A mixture of -yl isocyanate dimer (7 g), dimethylacecool of 2-methylaminoacetaldehyde (5 g) and ethyl acetate (50 TLl) was charged into a glass reactor equipped with a mechanical stirrer and a reflux condenser. .

The reaction mixture was heated under reflux for about 2 hours.

The solvent was then removed from the mixture under reduced pressure, yielding the desired product, 2-[1methyl-3-(5-cyclopropyl-
Dimethylacecool of 1,3,4thiadiazol-2-yl)ureido]acetaldehyde was obtained as an oil.

Example 3 ■-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-hydroxy-1,3
-Preparation of imidazolidin-2-one 2-[1-methyl-3(5-cyclopropyl-1,3,4-thiadiazol-2-yl) obtained from Example 2
[ureide] dimethyl acetaldehyde, water (400 ml) and hydrochloric acid (4 m0) were charged to a glass reactor equipped with a mechanical stirrer, a thermometer and a reflux condenser.

The reaction mixture was heated under reflux for about 15 minutes.

The reaction mixture was then filtered hot and the filtrate was cooled to form a precipitate.

The precipitate is collected by filtration, dried and recrystallized from ethyl acetate to give the desired product, mp 178-17.
1-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-hydroxy- at 9°C.
1,3-imidazolidin-2-one was obtained.

Example 4 5-cyclohexyl-1,3,4-thiadiazole-2
-Production of isocyanate dimer Ethyl acetate (500
A saturated solution of phosgene dissolved in 1111) was charged to a glass reactor equipped with a mechanical stirrer.

5-Cyclohexyl-2-amino-1,3,4-thiadiazole (6 g) was added to the reactor and the reaction mixture was heated and stirred under reflux for about 4 hours, resulting in the formation of a precipitate.

Then, nitrogen gas was blown into the reaction mixture to remove unreacted phosgene.

The mixture after blowing was then filtered to collect the precipitate.

This precipitate is then recrystallized from a mixture of dimethylformamide and water to give the desired product, mp 23
A 5-cyclohexyl-1,3,4-thiadiazol-2-yl isocyanate dimer having a temperature of 7 to 239°C was obtained.

Example 5 2-[1-methyl-3-(5-cyclohexyl 1.3,
Preparation of dimethylacecool from 4-thiadiazol-2-yl)ureido]acetaldehyde 5-cyclohexyl-1,3,4-thiadiazole-2
-yl isocyanate dimer (12 g), dimethylacecool of 2-methylamino-acetaldehyde (6,9
A mixture of g) and benzene (60 m7) was charged into a glass reactor equipped with a mechanical stirrer and a reflux condenser.

The reaction mixture was heated under reflux for about 15 minutes.

Thereafter, the solvent was removed from the mixture under reduced pressure to obtain a solid substance as a residue.

This residue is then recrystallized from methanol to give the desired product, 2-
[1-Methyl-3-(5cyclohexyl-1,3,5-
Dimethyl acetal of thiadiazol-2-yl)ureido]acetaldehyde was obtained.

Example 6 ■-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-hydroxy-1,3
-Production of imidazolidin-2-one 2-[1-methyl-3-(5-cyclohexyl-1,3
, 4-thiadiazol-2-yl)ureido] acetaldehyde dimethyl acecool (15 g), water (400
1 rLl) and hydrochloric acid (4 m0) were charged into a glass reactor equipped with a mechanical stirrer, thermometer and reflux condenser.

The reaction mixture was heated under reflux for about 15 minutes.

The reaction mixture was then filtered while hot and the p-liquid was cooled to form a precipitate.

The precipitate is collected by filtration, dried and recrystallized from methanol to give the desired product, mp 154-1
1-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)3-methyl-5-hydroxy- at 55°C
1,3-imidapridin-2-one was obtained.

Example 7 5-cyclobutyl-1,3,4-thiadiazole-2-
Production of isocyanate dimer Ethyl acetate (100 m
A saturated solution of phosgene dissolved in l) was charged to a glass reactor equipped with a mechanical stirrer.

A slurry of 5-cyclobutyl-2-amino-1,3,4-thiadiazole (45 g) in ethyl acetate (300 mO) was added to the reactor and the resulting mixture was stirred for about 16 hours, resulting in the formation of a precipitate.

Then, nitrogen gas was blown into the reaction mixture to remove unreacted phosgene.

The mixture after blowing was then filtered to collect the precipitate.

The desired product, 5-cyclobutyl-1,3,4-thiadiazol-2-yl isocyanate dimer, was then obtained by recrystallizing the precipitate.

Example 8 2-[1-propyl-3-(5-cyclobutyl 1.3.
Preparation of dimethyl acetal of 4-thiadiazol-2-yl)ureido]acetaldehyde 5-cyclobutyl-1,3,4-thiadiazole-2-
isocyanate dimer (0.05 mol), dimethyl acecool of 2-propylaminoacetaldehyde (0.05 mol),
, 1 mol) and benzene (60 TLl) were charged into a glass reactor equipped with a mechanical stirrer and a reflux condenser.

The reaction mixture was heated under reflux for about 15 minutes.

Thereafter, benzene was removed from the mixture under reduced pressure to obtain a solid product as a residue.

This residue is then recrystallized to yield the desired product, 2-[1-propyl-3-(5-cyclobutyl-1,
Dimethylacecool of 3,4-thiadiazol-2yl)ureido]acetaldehyde was obtained.

Example 9 l-(5-cyclobutyl-1,3,4-thiadiazol-2-yl)-3-propyl-5-hydroxy-1,3
-Production of imidazolidin-2-one 2-[1-propyl-3-[5-cyclobutyl-1,3
, 4-thiadiazol-2-yl)ureido] acetaldehyde dimethyl acecool (11), water (400 m
A) and hydrochloric acid (4 m) were charged into a glass reactor equipped with a mechanical stirrer, thermometer and reflux condenser.

The reaction mixture was heated under reflux for about 15 minutes.

The reaction mixture was then thermally filtered and the solution cooled to form a precipitate.

The precipitate is collected by filtration, dried and recrystallized to give the desired product, 1-(5-cyclobutyl 1.3,4
-thiadiazol-2-yl)-3propyl-5-hydroxy-1,3-imidazolidin-2-one was obtained.

Example 10 5-cyclopentyl-1,3,4-thiadiazole-2
-Production of isocyanate dimer Ethyl acetate (100
A saturated solution of phosgene dissolved in m7) was charged to a glass reactor equipped with a mechanical stirrer.

A slurry of 5-cyclopentyl-2-amino-1,3,4-thiadiazole (50 g) in ethyl acetate (300 mA) was added to the reactor and the reaction mixture was stirred for about 16 hours, resulting in the formation of a precipitate.

Then, nitrogen gas was bubbled into the reaction mixture to remove unreacted phosgene.

The mixture after blowing was then filtered to collect the precipitate.

The desired product 5 is then obtained by recrystallizing this precipitate.
-cyclopentyl-1,3,4-thiadiazole-2-
An isocyanate dimer was obtained.

Example 11 2-[l-methyl-3-(5-cyclopentyl 1.3,
Preparation of dimethylacecool from 4-thiadiazol-2-yl)ureido]acetaldehyde 5-cyclopentyl-1,3,4-thiadiazole-2
-yl isocyanate dimer (0,05 mol), dimethyl acecool of 2-methylaminoacetaldehyde (0
, 1 mol) and benzene (60 TLl) were charged into a glass reactor equipped with a mechanical stirrer and a reflux condenser.

The reaction mixture was heated under reflux for about 15 minutes.

Thereafter, benzene was removed from the mixture under reduced pressure to obtain a solid product as a residue.

The residue is then recrystallized to obtain the desired product 2-[
1-Methyl-3-(5-cyclopentyl-1,3,4-
Dimethylacecool of thiadiazol-2-yl)ureido]acetaldehyde was obtained.

Example 12 1-(5-cyclopentyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-hydroxy-1,3
-Production of imidazolidin-2-one 2- [1-methyl-3-(5-cyclopentyl 1.3
, 4-thiadiazol-2-yl)ureido] acetaldehyde dimethyl acecool (15 g), water (400
11 LA) and hydrochloric acid (4 m) were charged to a glass reactor equipped with a mechanical stirrer, thermometer and reflux cooler.

The reaction mixture was heated under reflux for about 15 minutes.

The reaction mixture was then filtered while hot, and the F solution was cooled to form a precipitate.

This precipitate is collected by filtration, dried and recrystallized to obtain the desired product, 1-(5-cyclopentyl-1,
3,4-thiadiazol-2-yl)-3=methyl-5
-Hydroxy-1,3-imidazolidin-2-one was obtained.

Example 13 5-cycloheptyl-1,3,4-thiadiazole-2
-Production of isocyanate dimer Ethyl acetate (100
A saturated solution of phosgene dissolved in m0 was charged to a glass reactor equipped with a mechanical stirrer.

A slurry of 5-cyclohebutyl-2-amino-1,3,4-thiadiazole (51) in ethyl acetate (300 mO) was added to the reactor, and the resulting reaction mixture
When the mixture was stirred for an hour, a precipitate was formed.

Then, nitrogen gas was bubbled into the reaction mixture to remove unreacted phosgene.

After blowing, the mixture was then filtered to collect the precipitate.

The desired product is then obtained by recrystallizing this precipitate.
5-cycloheptyl-1,3,5-thiadiazole-2
-yl isocyanate dimer was obtained.

Example 14 2-[1-methyl-3-(5-cycloheptyl 1.3.
Production of dimethyl acetal of 4-thiadiazol-2-yl)ureido]acetaldehyde 5-cycloheptyl-1,3,4-thiadiazole-2
-yl isocyanate dimer (0,05 mol) 2-methylaminoacetaldehyde dimethylacecool (0,05 mol)
A mixture of 1 mol) and benzene (60 ml) was charged into a glass reactor equipped with a mechanical stirrer and a reflux condenser.

The reaction mixture was heated under reflux for about 15 minutes.

Thereafter, benzene was removed from the mixture under reduced pressure to obtain a solid product as a residue.

This residue is then recrystallized to obtain the desired product, 2-[1-methyl-3-(5-cycloheptyl-1
, 3,4-thiadiazol-2-yl)ureido] dimethylacecool of acetaldehyde was obtained.

Example 15 1-(5-cycloheptyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-hydroxy-1,3
-Production of imidazolidin-2-one 2-[1-methyl-3-(5-cycloheptyl-1,3
, 4-thiadiazol-2-yl)ureido] acetaldehyde dimethylacecool (15 g), water (400
ml) and acetic acid (4 ml) were charged into a glass reactor equipped with a mechanical stirrer, thermometer and reflux condenser.

The reaction mixture was heated under reflux for about 15 minutes.

The reaction mixture was then heated in a hot oven and the filtrate was cooled to form a precipitate.

By recovering this precipitation, drying and recrystallizing the desired product, ■-(5-cycloheptyl-1°3.4
-thiadiazol-2-yl)-3-methyl-5-hydroxy-1,3-imidacillin-2-one was obtained.

Example 16 Preparation of 5-(1-methylcyclohexyl)-1,3°4-thiadiazol-2-yl isocyanate dimer A saturated solution of phosgene dissolved in ethyl acetate (100 ml) was prepared with a mechanical stirrer. The mixture was charged into a glass reactor.

Ethyl acetate (5(1-methylcyclohexyl)-2-amino-1゜3.4-thiadiazole (6
The slurry containing g) was added to the reactor and the resulting mixture was stirred for about 16 hours, resulting in the formation of a precipitate.

Then, nitrogen gas was bubbled into the reaction mixture to remove unreacted phosgene.

By filtering the blown mixture, the desired product, 5-(1-methylcyclohexyl)-1,3,4-
Thiadiazol-2-yl isocyanate dimer was obtained.

Example 17 Preparation of dimethylacecool of 2-(1-methyl-3-(5-(1-methylcyclohexyl)-1,3,4-thiadiazol-2-ylioreido)acetaldehyde 5-(1-methylcyclohexyl)-1 ,3゜4-thiadiazol-2-yl isocyanate dimer (7,5,
? ), 2-methylaminoacetaldehyde in dimethylacecool (5 g) and ethyl acetate (50 mA') was charged into a glass reactor equipped with a mechanical stirrer and a reflux condenser.

The reaction mixture was heated under reflux for about 2 hours.

The desired product, 2-(1-methyl-3-[5(
Dimethylacecool of l-methylcyclohexyl)-1,3,4-thiadiazol-2-ylioreido)acetaldehyde was obtained.

Example 18 1-(5-(1-methylcyclohexyl)-1°3.4
-Production of thiadiazol-2-yl-3-methyl-5-hydroxy-1,3-imidazolidin-2-one 2-(1-methyl-3(5-1-methylcyclohexyl)-1,3,4-thiadiazole) -2il〕ureid)
Acetaldehyde dimethyl acecool, water (400m
and hydrochloric acid (4 ml) were charged into a glass reactor equipped with a mechanical stirrer, a thermometer and a reflux condenser.

The reaction mixture was heated under reflux for about 15 minutes.

The reaction mixture was then filtered hot, and the synovial fluid was cooled to remove the precipitate.

The precipitate is collected by filtration, dried and recrystallized to yield the desired product, 1-(5-(1-methylcyclohexyl)-1,3,4-thiadiazol-2-yl-3-
Methyl-5-hydroxy-1,3-imidacillin-2-
Got it on.

Example 19 Preparation of 5-(4-chlorocyclohexyl)-1,3°4-thiadiazol-2-yl isocyanate dimer A saturated solution of phosgene dissolved in ethyl acetate (500 mO) was prepared with a mechanical stirrer. It was charged into a glass reactor.

5-(4-chlorocyclohexyl)2-amino-1,3
, 4-thiadiazole (6 g) was added to the reactor and the resulting mixture was heated under reflux for about 4 hours, when the precipitate was removed.

Then, nitrogen gas was bubbled through the reaction mixture to filter out unreacted phosgene.

The mixture after blowing was then filtered to collect the precipitate.

The desired product is then obtained by recrystallizing this precipitate.
A dimer of 5-(4-chlorocyclohexyl)-1,3,4-thiadiazol-2-yl isocyanate was obtained.

Example 20 Preparation of dimethylacecool of 2-(l-ethyl-3-(5-(4-chlorocyclohexyl)-1,3,4-thiadiazol-2-ylioreido)acetaldehyde 5-(4-chlorocyclohexyl)-1 ,3゜4-thiadiazol-2-yl isocyanate dimer (1:1l
l), 2-ethylaminoacetaldehyde, a mixture of dimethylacecool (6.9 g) and benzene (60 mA) was charged into a glass reactor equipped with a mechanical stirrer and a reflux condenser.

The reaction mixture was heated under reflux for about 15 minutes.

Thereafter, benzene was removed from this mixture under reduced pressure to obtain a solid product as a residue.

This residue was then recrystallized to obtain the desired product, 2-(1-ethyl-3-(5-4-chlorocyclohexyl)-1°3.4-thiadiazol-2-ylioreido)acetaldehyde.

Example 21 1-(5-(4-chlorocyclohexyl)-1°3.4
-Production of thiadiazol-2-yl-3-ethyl-5-hydroxy-1,3-imidazolidin-2-one 2-(1-ethyl-3-(5-(4-chlorocyclohexyl)-1,3,4 -thiadiazol-2-ylioreido)acetaldehyde in dimethyl acecool (15g)
), water (400 mJ) and hydrochloric acid (4 m) were charged into a glass reactor equipped with a mechanical stirrer, thermometer and reflux condenser.

The reaction mixture was heated under reflux for about 15 minutes.

The reaction mixture was then thermally filtered and the p-liquid was cooled to form a precipitate.

The precipitate was collected by filtration, dried and recrystallized to yield the desired product, 1-[5(4-chlorocyclohexyl)-1,3,4-thiadiazol-2-yl-3
-ethyl-5-hydroxy-1,3-imidazolidine-
2-on was obtained.

Other compounds falling within the scope of the present invention that can be prepared by the methods of the above examples include the following.

1-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-3-ethyl-5-hydroxy-1,3
-Imidazolidin-2-one, 1-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-3-propyl-5-hydroxy-1,3-imidazolidine-2
-one, 1-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-3-butyl-5-hydroxy-1,3-imidazolidin-2-one, ■-(5-cyclopropyl -1,3,4-thiadiazol-2-yl)
-3-pentyl-5-hydroxy-1,3-imidazolidin-2-one, -(5-cyclopropyl-1,3,
4-thiadiazol-2-yl)-3-hexyl-5-
Hydroxy-1,3-imidazolidin-2-one, 1-
(5-cyclohexyl-1,3,4-thiadiazole-
2-yl)-3-ethyl-5-hydroxy-1,3-imidazolidin-2-one, ■-(5-cyclohexyl-
1,3,4-thiadiazol-2-yl)-3-propyl-5-hydroxy-1,3-imidazolidin-2-one, -(5-cyclohexyl-1,3,4-thiadiazol-2-yl) )-3-butyl-5-hydroxy-1
, 3-imidazolidin-2-one, ■-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)-3
-pentyl-5-hydroxy-1,3-imidazolidin-2-one, 1-(5-cyclohexyl-1,3,4-
Thiadiazol-2-yl)-3-hexyl-5-hydroxy-1,3-imidazolidin-2-one, 1-(5
-cyclobutyl-1,3,4-thiacyfusol-2-yl)-3-ethyl-hydroxy 1,3-imidazolidin-2-one, -(5-cyclopentyl-1,3,4-thiadiazol-2-yl) )-3-ethyl-5-hydroxy-1,3
-Imidazolidin-2-one, ■-(5-cycloheptyl-1,3,4-thiadiazol-2-yl)-3-ethyl-5-hydroxy-1,3-imidazolidine-2-
on, 1-(5-(2-methylcyclopropyl)1゜3
．． 4-Thiadiazol-2-ylio3-methyl-5-
Hydroxy-1,3-imidacillin-2-one, 1-(5-(2-methylcyclobutyl)-1゜3.4-
Thiadiazol-2-yl)-3-methyl-5-hydroxy-1,3-imidapridin-2-one 1-(5-(3-methylcyclopentyl)-1°3.4
-thiadiazol-2-yl)-3-methyl-5-hydroxy-1,3-imidazolidin-2-one, 1-(5-(i-propylcyclopentyl)-1,3,
4-thiadiazol-2-ylyo3=methyl-5-hydroxy-1,3-imidazolidin-2-one, 1-(5-(3-hexylcyclohexyl) 1.3.4
-thiadiazol-2-ylio3-methyl-5-hydroxy-1,3-imidapridin-2-one, 1-(5-(4-bromocyclohexyl)-1°3.4
-Thiadiazol-2-ylio3-methyl-5-hydroxy-1,3-imidazolidin-2-one, 1-(5-(3-hydroxycyclohexyl)1.3.
4-thiadiazol-2-ylyo3=methyl-5-hydroxy-1,3-imidazolidin-2-one, 1-(5-(4-methoxycyclohexyl)-1,3,
4-thiadiazol-2-yl-io3-methyl-5-hydroxy-1,3-imidapridin-2-one, 1-(5-(4-butoxycyclohexyl)-1,3,
4-Thiadiazol-2-ylyo3-methyl-5-hydroxy-1,3-imidazolidin-2-one, 1-(5-(3-hexyloxycyclohephthyl)-1
,3,4-thiadiazol-2-yl]3-methyl-5
-Hydroxy-1,3-imidazolidin-2-one, For practical use as herbicides, the compounds of the invention are usually prepared in a herbicidal composition containing an inert carrier and a herbicidally toxic amount of such compound. mixed into the agent composition.

Such herbicide compositions are also called formulations, but
These make it possible to conveniently apply the active compounds to weed-infested areas in any desired amount.

These compositions may be solids, such as powders, granules, or wettable powders, or liquids, such as solutions, aerosols, or emulsifiable concentrates.

For example, powders can contain active compounds such as talc, clay, silica,
It can be produced by powdering and blending with a solid inert carrier such as pyrophyl Iite.

Granular formulations usually include this compound dissolved in a suitable solvent, such as attapu-Igite or vermiculite, usually having a particle size of about 0.3 to 1.5 mm. ) can be produced by impregnating it on or into a granulated carrier.

Wettable powders, which can be dispersed in water or oil to any desired concentration of active compound, can be prepared by incorporating a wetting agent into a concentrated powder composition.

In some cases, the active compounds are sufficiently soluble in common organic solvents such as kerosene or xylene, so that they can be used as solutions in the abovementioned solvents.

Often, herbicide solutions can be dispersed as an aerosol under pressure.

However, preferred liquid herbicidal compositions are emulsifiable concentrates, which contain the active compound according to the invention and as an inert carrier a solvent and an emulsifier.

Such emulsifiable concentrates can be diluted with water and/or oil to any desired concentration for application as a spray to weed-infested areas.

The emulsifier most commonly used in this concentrate is a nonionic surfactant or a mixture of nonionic and anionic surfactants.

By using several emulsifier systems, inverse emulsions can be produced that can be applied directly to weed growth sites.

Typical herbicidal compositions according to the invention are illustrated by the following examples.

Amounts in Examples are based on parts by weight.

Example 22 Preparation of Powder Product of Example 3 10 Powdered Talc 90 The above aliquots were ground in a mechanical grinding compounder until a homogeneous free-flowing powder with the desired particle size was obtained. .

This powder is suitable for direct application to weed-infested areas.

The compositions of the invention can be applied as herbicides by any method known in the art.

One method of controlling weeds is to contact weed-growing areas with a herbicidal composition containing an inert carrier and a compound of the invention as a substantial active ingredient in an amount that is toxic to the weed as a herbicide. Consisting of

Although the concentration of the novel compounds of the present invention in herbicidal compositions will vary widely depending on the formulation and intended purpose, typically the herbicidal compositions will contain about 0.0% of the active compound of the present invention.
Contains 5 to 95% by weight.

In a preferred embodiment of the invention, the herbicidal composition contains about 5-75% by weight of active compound.

The composition may also contain other pesticides, such as insecticides, nematode killers, fungicides; stabilizers, dispersants, killing agents, adhesives, etc.
Additional substances such as adhesives, fertilizers, activators, synergists, etc. may also be included.

The compounds of the present invention are also useful in combination with other herbicides and/or defoliation promoters, desiccation promoters, growth inhibitors, etc. in the herbicidal compositions described above.

These other materials can contain from about 5 to 95% of the active ingredient in the herbicidal composition.

By using these other herbicides and/or defoliation accelerators, desiccation accelerators, etc. in combination with the compounds of the present invention, a herbicidal composition that is more effective in controlling weeds can be provided, and Each herbicide individually provides results that cannot be obtained by forming individual herbicides into separate compositions.

Other herbicides, defoliation promoters, desiccation promoters and growth inhibitors that can be used in herbicidal compositions to control weeds with the compounds of this invention include the following:

2.4-D, 2,4.5-T, MCPA, MCPB.

4 (2,4-DB), 2,4-DEB, 4-CPB,
4-CPA, 4-CPP, 2.4.5-TB, 2°4.
Chlorphenoxy herbicides such as 5-TES, 3,4-DA, Silvex; IPC, CIPC, Sweep, Burpan, BCPC,
Carbamate herbicides such as CEPC and CPPC; CDEC1 mekim sodium, EPTC1 sialate,
Thiocarbamate and dithiocarbamate herbicides such as PEBC, Perplate, Varut; Lua, Diduron, Zinloral Urea, Chlorcuron, Cycluron, Fenuron, Monolon, Monolon TCA
Substituted urea herbicides such as , diuron, linuron, monolinuron, nephron, fuduron, trimeteuron; symmetrical triazines such as simazine, phlorazine, atraone, desmetrin, furanone, ipazine, promethrin, acudin, trietazine, dimedone, promethone, propazine, ametrine, etc. Chloracetamide herbicides such as 4-(chloroacetyl)morpholine and 1-(chloroacetyl)piperidine; TCA1 Darapon, 2,3-dichloropropionic acid, 2
, 2,3-TPA and other chlorinated aliphatic acid herbicides; 2.3,6-TBA, 2,3,5,6-TBA, dicamba, trichampa, amiben, phenac, PBA, 2-
Methoxy-3,6-dichlorophenylacetic acid, 3-methoxy-2,6-dichlorophenylacetic acid, 2-methoxy-3
, 5,6-dolychlorophenylacetic acid, 2,4-dichloro-3-nitrobenzoic acid and other chlorinated benzoic acids and phenylacetic acid herbicides; aminotriazole, maleic hydrazide, mercuric phenylacetate, Endosal, Biuret, industrial chlordane, dimethyl 2,3,5.6-titrachloroterephthalate, diquat, Arbon, DNC, DNBP, dichlobenil, DPA, diphenamide, dibrovaline, trifluralin, puran, cyclyl, Marphos, DMPA,
, DSMAlMSMA, Potassium Azido, Acrolein, Benefin, Bensuride, AMS1 Bromacil, 2-
(3,4-dichlorophenyl)-4-methyl-1°2.
4-oxadiazolidine-3,5-dione, bromoxynil, cacodylic acid, CMA, CPMF, cypromid,
DCBL1DCPA, Zicron, Diphenatrile, DMT
T, DNAP, EBEP, EXD, HCA, ioxynil, IPX1 isosyl, potassium cyanate, MAAlM
AMAlMCPES, MCP P, MH, Molinate,
NPAloCH, baraquat, PCP, picloram,
DPA, PCA, pychlor, sesson, terbasil,
Terbutol, TCBA, Brominyl, CP-5014
4, H-176-1, H-732, M-2901, pranavin, sodium tetraborate, calcium cyanamide, DEF, ethylxanthogen sulfide, synthon, synthon B1 propanyl, etc.

Such herbicides may also be used in the compositions of the present invention in the form of their salts, esters, amides, and any other derivatives applicable to this particular parent compound.

Weeds are undesirable plants that grow where they are not desired and have economic value, interfering with the production of crops, the growth of ornamental plants, or the sanitary environment of livestock.

Many of the weeds are well known, such as pigweed and lamb's quarters.
mbsquarters), foxtail (fo
xtail), crabgrass (cr-abgras)
s), wild mustard (wild mu -5t
ard), field pennycress (fieldpen
nycres s), ryegrass
), goose grass, ch ickweed, wildoats, velvet leaf (ve)
lvet 1eaf), purslin (purs 1a
ne), barnyard grass (barnya-rdg)
rass), smartweed (smar twee)
d), knotweed, cocklebar, wild buckwheat, kochia, mesoic
), corrt-cockle, ragweed, sowweed (
sowthistle), coffee weed (cof
feeweed), croton, cuphea, dodder
, fumitory, ground cell (
ground-sel), hempnettle
et t le), knawel, spurge, spurley (5pur r
y), emex, jungle rice, pontweed
dweed), dog fennel (dogfen-nc)
l), carpe tweed
), Morning Glory
y), bedstraw, duck salad, nai
ad), cheatgrass, fallpauicum, Jimsonweed, witchgrass, switchgrass (
swi-tchgrass), water glass (wa
tergrass), teaweec
Q Annual plants such as wildturnip and sprangletop; wild carrot,
Matricaria (matr 1caria), wildbar ley (wildbar ley), champion (campion), chamomile (chamomile)
le), burdock, marine (
Mullein), Rowntree Tomarrow (rou)
nd Ieaved marnow), bull thistle, houun-dstongue, mosmarine (mot
biennials such as H mul 1ein) and purple 5 tarthistle; white cockle, perennial rye grass;
ass), quackgras s
), Johnson grass
), canadathistle
, hedgebindweed (hedgeb indwe)
ed), Bermuda gr
ass), sheepsorrel (5heepsorrel)
), curly dock, nutgrass, field chickweed, dandel one, campanula (ca
mpanula), field pinweed (f.
1eld bindweed), dump lion (
dandel ion), campanula (camp
anu 1 a), field pinweed (f
1eld bindweed), Russian knapweed, mesquid, toad
flax), yarrow, astar, gromweed
), horsetail, ironweed, sesbania (5
esbania), bullrush,
cattail, wintercress, horsetail
rse-nettle), nutsed
ge ), milkweed and sicklepod.

Similarly, such weeds can be classified as broad-leaved weeds or green grasses.

It is economically desirable to control these weeds without harming beneficial plants or livestock.

This novel compound of the invention is of particular value for weed control.

This is because while they are relatively non-toxic to many beneficial plants, they are toxic to many species and groups of weeds.

The exact amount of this compound required depends on a variety of factors, including the hardness of the particular weed species, weather, soil type, method of application,
It depends on the types of beneficial plants in the same area.

Therefore, for good control of lightly bushy weeds growing under unfavorable conditions, approximately 1 or 2
Applying less than an ounce (less than 0.7 or 1.B/are) of active compound may be sufficient to provide good control of dense, hardy perennial weeds that grow under favorable conditions. may require application of 10 pounds (110 g/are) or more of active compound per kneeker.

The herbicidal toxicity of the novel compounds of the present invention can be demonstrated by a number of well-known and established test methods in the art, such as pre-emergence and post-emergence tests.

The herbicidal effect of the compounds of the present invention was demonstrated by experiments conducted for pre-emergence control of various weeds.

In these experiments, seeds of various weeds were sown in small plastic greenhouse pots filled with dry soil.

Within 24 hours after sowing, the soil was watered until moist and the test compound, formulated as an aqueous emulsion in acetone solution containing an emulsifier, was sprayed onto the soil surface at the indicated concentration.

After spraying, place the soil container in the greenhouse and replenish the necessary heat.
Water was withdrawn once or more per day.

The plants were kept under the above conditions for about 15-21 days, at which point the condition of the plants and the degree of damage to the plants were determined as follows:
Evaluation was made on a scale of 10 to 10.

〇-Damage 0% 1 = '' 10%l Slight damage 2-7720% 0 3- `` 30%) Moderate damage 4 = /740% 5- '' 50%) Slight damage 6-7760% 7 = // 70% 8- /780% Very severe damage 9=//90% 10-77100% Death The action of the compound of the present invention is evidenced by the following data.

The herbicidal efficacy of the compounds of the present invention was also demonstrated by experiments conducted for the post-emergence control of various weeds.

In these experiments, the compound to be tested was formulated as an aqueous emulsion and sprayed at the indicated dose onto the leaves of weeds that had reached a defined size.

After spraying, the plants were placed in a greenhouse and watered daily or more frequently.

Water was not poured onto the leaves of the treated plants.

The severity of the damage was measured 10-15 days after treatment and
Rated on a scale of ~10.

The effectiveness of these compounds is evidenced by the following data.

Comparative Example A post-germination weed suppression test was conducted on the compounds shown in Table 3 in the same manner as described above.

This compound is a dihydroxy compound in which a hydroxyl group is further added to the 4-position of the compound of Example 3.

The experimental results are shown in Table 3 below.

Table 3

Claims (1)

[Scope of Claims] 1. A herbicidal composition containing an inert carrier and an amount of a compound represented by the following formula that is toxic to weeds as an essential active ingredient. (In the formula, R1 is cycloalkyl of 3 to 7 carbon atoms, and R2 is alkyl of 1 to 3 carbon atoms.)