IE44565B1 - Herbicidally active 2-dimethylcarbomoylimino-1,3,4-thiadiazolin-3-ide derivatives, process for their manufacture and their use - Google Patents
Herbicidally active 2-dimethylcarbomoylimino-1,3,4-thiadiazolin-3-ide derivatives, process for their manufacture and their useInfo
- Publication number
- IE44565B1 IE44565B1 IE346/77A IE34677A IE44565B1 IE 44565 B1 IE44565 B1 IE 44565B1 IE 346/77 A IE346/77 A IE 346/77A IE 34677 A IE34677 A IE 34677A IE 44565 B1 IE44565 B1 IE 44565B1
- Authority
- IE
- Ireland
- Prior art keywords
- ide
- thiadiazolin
- dimethylcarbamoylimino
- salt
- compound
- Prior art date
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Herbicidally active 2-dimethylcarbamoylimino-1,3,4-thiadiazolin-3-ide derivatives of the general formula I in which R represents an aliphatic hydrocarbon group, B represents a monovalent metal equivalent and n represents 0, 1 or 2.
Description
The present invention is concerned with new herbicidally active 2 - dimethyl carbamoyl imino - 1,3,4 - thiadiazolin - 3 - ide derivatives, with a proii'ss for the manufacture' of those compounds and with their use.
- (1,3,4 - thiadiazol -2-yl) - urea derivatives having a herbi5 cidal action have already been known (German Offen!egungsschriften Nos.
1,816, 696 and 2,118,520). However, they have only a very limited spectrum of selectivity towards crop plants.
Accordingly, the problem upon which the present invention is based has been to make available a herbicidal agent, which, in addition to having an outstanding action against weeds, ,has a broad spectrum of selectivity towards crop plants.
This problem is solved in accordance with the present invention by the compounds of the general formula I, as defined below.
The present invention accordingly provides compounds of the general 15 formula I
N-N-B
I /CH3
R-S(0)n-C C=N-CO-NX (I) ch3 in which R represents an aliphatic hydrocarbon group, B represents a monovalent metal equivalent and n^ represents 0, 1 or 2.
The compounds of the present invention are distinguished by a 20 broad soil- and leaf-herbicidal action. They can be used for combating mono- or di-cotyledonous weeds (including certain undesired plants not normally considered as. weeds).
With the compounds of the present invention there can be combated by the pre-emergerice method and also the post-emergence method agricultural
- 2 4 4 5 G S weeds amongst which there may be mentioned, for example, Sinapis ssp., Stellaria media, Senecio vulgaris, Matricaria chamomi11 a, Ipomoea purpurea, Chrysanthemum segetum, Lamium amplexicaule, Centaurea cyanus, Amaranthus retroflexus, Alopecurus myosuroides, Echinochloa crus gal 1i, Setaria ; italica, Sorphum halepense and Lolium perenne.
For combating weed seeds there are generally used quantities within the range of from 1 kg of active substance per hectare to 5 kg of the active substance per hectare. Thereby, the active compounds of the present invention have been found to be selective in commercial vegetable
TQ crops, for example bush-bean, ground-nut, potato, pea, rice, maize, sorghum and soya crops. When two or more compounds of the general formula I are used the range of 1 kg to 5 kg refers of course to the total amount applied of these compounds.
At higher rates of application the compounds are also suitable as total herbicides for the destruction or suppression of waste land flora during a period of growth.
The present invention accordingly also provides a herbicidal preparation which comprises a compound of the general formula I, in admixture or conjunction with a suitable carrier. The preparation may of course contain one or more compounds of the general formula I.
The present invention further provides a method of protecting a living plant against weeds, wherein the area in the vicinity of a living plant is treated with a compound of the general formula I.
The present invention further provides a method of protecting a 25 crop area against weeds, wherein a crop area is treated with a compound of the general formula I.
- 3 445G5
The present invention further provides a method of protecting a waste land against weeds, wherein a waste land is treated with one or more compounds of the general formula I, the compound(s) being used in a total amount of more than 5 kg per hectare.
The present invention further provides a pack which comprises a compound of the general formula I together with instructions for its use as a selective herbicide.
The compounds of the present invention may be used either alone, or in admixture with one another or with other active substances. If desired, there may be added other defoliating, plant protecting or pest combating agents depending on the purpose desired.
When it is intended to broaden the spectrum of action, other herbicides may also be added. For example, there are suitable as herbicidally active components to be added active substances of the group of triazines, aminotriazoles, anilides, diazines, uracils, aliphatic carboxylic acids and halogenocarboxylic acids, substituted benzoic acids and aryloxy carboxylic acids, hydrazides, amides, nitriles, esters of such carboxylic acids, carbamic acid esters and thiocarbamic acid esters, ureas, 2,3,6trichlorobenzyloxy - propanol and thiocyanate-containing agents. As other additives there are also to be understood, for example, nonphytotoxic additives, which cause a synergistic increase in action with herbicides, for example wetting agents, emulsifiers, solvents and oily additives.
The active compounds of the general formula I or mixtures thereof are advantageously used in the form of herbicidal preparations, for example powders, strewable preparations, granules, solutions, emulsions
- 4 4 4 S 6 5 or suspensions with the addition of liquid and/or solid vehicles or diluents, and, if desired, of surface-active agents, for example wetting, adherent, emulsifying and/or dispersing agents.
Suitable liquid carriers are, for example, water, aliphatic hydro5 carbons, aromatic hydrocarbons, for example benzene, toluene and xylene, cyclohexanone, isophorone, dimethyl sulphoxide and dimethylformamide, and also mineral oil fractions.
As solid carriers there are suitable, for example, mineral earths, for example tonsil, silica gel, talcum, kaolin, attaclay, limestone and silicic acid, and vegetable products, for example meals.
As surface-active agents there may be mentioned, for example, calcium lignin sulphonate, polyoxyethylene alkylphenol ethers, naphthalene sulphonic acids and salts thereof, phenol sulphonic acids and salts thereof formaldehyde condensates, fatty alcohol sulphates and also substituted benzene sulphonic acids and salts thereof.
The total amount of the active compound(s) of the general formula I in the various herbicidal preparations may vary within wide limits. For example, the preparations may contain 10 to 80% by weight of active compound^), 90 to 20% by weight of liquid or solid carrier and, if desired, also up to 20% by weight of surface-active agent(s).
The active compounds may be applied in the usual manner, for example with water as carrier in quantities of spray liquor· of 100 to 1000 litres per hectare. It is also possible to apply the active compounds by the so-called low-volume and ultra-low-volume methods and it is also possible to apply them in the form of so-called microgranules.
Among the compounds of the general formula I there may be used in
- 5 4 4 5 6 5 accordance with the present invention, more especially, those in which R represents an alkyl, alkenyl or alkynyl group containing up to 6 carbon atoms and B represents an alkali metal atom, preferably a lithium, sodium or potassium atom.
As alkyl, alkenyl and alkynyl groups there come into consideration for this purpose, for example, straight-chained and branched alkyl, alkenyl and alkynyl groups, for example methyl, ethyl, propyl, isopropyl, allyl, 2 - propynyl, n - butyl, isobutyl, sec. - butyl, tert. - butyl,
- butenyl, 1 - methyl - 2 - propenyl, n - pentyl, isopentyl, neopentyl, tert. - pentyl, 1 - methyl butyl, 1 - ethyl - propyl, n - hexyl and isohexyl groups.
The compounds of the present invention of the general formula I are salts, which exist ionically corresponding to the following polar formulae
- 6 4 4 5 6 5 or formulated in general as
R-(0)n
for the sake of simplicity these ionic forms are not shown by the general formula I, but it is to be understood herein that each compound of the general formula I includes any one of the aforesaid ionic forms. The new compounds of the general formula I may be prepared, for example, by the process of the present invention, as defined below.
The present invention accordingly further provides a process for the manufacture of a compound of the general formula I, wherein 10 (a) dimethyl carbamoyl chloride of the formula II
H3C
N-CO—Cl (Π) h3c ts reacted in the presence of an acid-binding agent with a 1,3,4 - thia diazolylamine of the general formula III
II II ,c - nh2 (III) in which R and in have the meanings given above, to form a 2 - (dimethyl
- 7 44S6S carbamoyl imino) - 1,3,4 - thiadiazolin - 3 - carboxylic acid dimethyl amido derivative of the general formula IV
co-ir
N-hr ch3 W
N '''CHa in which R and ji have the meanings given above, which is split with a 5 metal compound of the general formula V
BY (V) in which B has the meaning given above and Y represents a hydrogen atom or a hydroxyl, Cx—C3 - alkoxy or amino group, or (b) a 1 - (1,3,4 - thiadiazol - 2- yl) - 3,3 - dimethylurea derivative of the general formula VI n· n
R-S(O) -C C-NH-CO-N \/ xch3 (VI) in which R and n have the meanings given above, is reacted with a metal compound of the general formula V
BY in which B and Y have the meanings given above.
(V)
- 8 4 4 5 6 S
Each step of the process of the present invention may, if desired, be carried out in the presence of a solvent.
The reaction of the components is preferably carried out at between 0° and 100°C, but generally at room temperature.
For the synthesis of the compounds of the present invention the reactants are advantageously used in approximately equimolar amounts.
As reaction media there are suitable polar organic solvents, alone or in admixture with water. Their choice depends, according to generally known view-points, on the metal compounds of the general formula BY used.
As solvents or suspension media there may be mentioned amongst many, for example, acid amides, for example dimethylformamide, acid nitriles, for example acetonitrile, alcohols, for example methanol and ethanol, and ethers, for example tetrahydrofuran.
The isolation of the compounds of the present invention formed is carried out finally by distilling off the solvent used under atmospheric or a reduced pressure or by precipitation with less polar organic solvents, for example with ketones, for example acetone, or ethers, for example diisopropyl ether.
Some specific compounds of the present invention are listed in the following Table:
TABLE
Name of the Compound
Potassium salt of 5-ethylthio-2-(dimethylcarbamoy1imi no)-1,3,4-thi adi azoli n-3-i de
Sodium salt of 2-(dimethylcarbamoylimino)-5methylsulphony!-1,3,4-thi adi azoli n-3-i de
Physical Constant
M.p. >250°C
M.p. >250°C
- 9 Name of the Compound
Sodium salt of 2-(dimethylcarbamoylimino)-5propylthi o-1,3,4-thi adi azoli n-3-i de
Potassium salt of 2-(dimethylcarbamoylimino)-5propylthio-1,3,4-thi adi azoli n-3-i de
Potassium salt of 2-(dimethylcarbamoyliminio)-5methy1thio-1,3,4-thi adi azoli n-3-i de
Potassium salt of 5-ethylsu1phonyl-2-(dimethylcarbamoyl imi no)-1,3,4-thi adi azol i n-3-i de
Sodium salt of 5-ethylthio-2-(dimethy1carbamoylimino)-l,3,4-thiadiazolin-3-ide
Sodium salt of 2-(dimethylcarbamoylimino)-5methylthio-1,3,4-thi azoli n-3-ide
Sodium salt of 5-butylthio-2-(dimethylcarbamoylimino)-l,3,4-thiadiazolin-3-ide
Potassium salt of 5-butylthio-2-(dimethylcarbamoylimi no)-l,3,4-thi adi azoli n-3-i de
Lithium salt of 5-butylthio-2-(dimethylcarbamoylimino)-l,3,4-thiadiazolin-3-ide
Sodium salt of 5-ethy1sulphonyl-2-(dimethylcarbamoylimi no)-l,3,4-thi adi azolin-3-ide
Potassium salt of 2-(dimethylcarbamoylimino)5-methylsulphonyl-1,3,4-thi adi azoli n-3-i de
Sodium salt of 2-(dimethylcarbamoy1imino)-5methylsulphi nyl-1,3,4-thiadiazoli n-3-i de
Physical Constant
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
- 10 4 4 5 6 S.
Name of the Compound
Potassium salt of 2-(dimethylearbamoylimino)5-methylsulphi nyl -1,3,4-thi adi azoli n-3-ide
Sodium salt of 2-(dimethylcarbamoyliminio)-55 (2-propynylthio)-l,3,4-thiadiazolin-3-ide
Potassium salt of 2-(dimethylcarbamoylimino)-5~ (2-propynylthio)-l,3,4-thiadiazolin-3-ide
Lithium salt of 5-ethylthi0-2-(dimethyl carbamoyl imino)-!,3,4-thi adi azoli n-3-ide
- Lithium salt of 2-(dimethylcarbamoylimino)-5methylthi o-l,3,4-thi adi azoli n-3-i de
Sodium salt of 2-(dimethylcarbamoylimino)-5isopropylthio-1,3,4-thiadiazolin-3-ide
Potassium salt of 2-(dimethylcarbamoylimino)-515 isopropylthio-1,3,4-thiadiazolin-3-ide
Sodium salt of 2-(dimethylcarbamoylimino)-5 (2-methyl-2-propenylthi o)-l,3,4-thi adiazoli n3-ide
Potassium salt of 2-(dimethylcarbamoylinrino)-520 (2-methy1-2-propenylthio)-1,3,4-thiadiazolin3-ide
Potassium salt of 2-(dimethylcarbamoylimino)-5hexylsulphonyl-1,3,4-thiadiazolin-3-ide
Sodium salt of 2-(dimethylcarbamoylimino)-525 hexylsulphinyl-1,3,4-thiadiazolin-3-ide
Physical Constant
M.p. 230°C (decomposition)
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. 213°C (decomposition)
M.p. 236°C (decomposition)
- 11 44SG5
Name of the Compound
Potassium salt of 2-(dimethylcarbamoylimino)-5hexylsulphi nyl-1,3,4-thi adi azoli n-3-i de
Lithium salt of 2-(dimethyl carbamoyl imino)-55 hexylsulphinyl-1,3,4-thiadiazolin-3-ide
Lithium salt of 2-(dimethylcarbamoylimino)-5i sobutylsulphi nyl -1,3,4-thi adi azolin-3-ide
Lithium salt of 2-(dimethylcarbamoylimino)-5pentylsulphony!-1,3,4-thi adi azoli n-3-i de
Sodium salt of 2-(dimethylcarbamoylimino)-bi sobutylsulphi nyl-1,3,4-thi adi azoli n-3-i de
Potassium salt of 2-(dimethylcarbamoylimino)-5i sobutylsulphi nyl-1,3,4-thi adi azoli n-3-i de
Lithium salt of 2-(dimethylcarbamoylimino)-515 hexylthio-1,3,4-thiadiazolin-3-ide
Sodium salt of 2-(dimethylcarbamoyl imino)-5hexylthi o-l,3,4-thi adi azolin-3-i de
Potassium salt of 2-(dimethylcarbamoylimino)-5hexylthi o-l,3,4-thi adi azoli n-3-i de
Sodium salt of 2-(dimethylcarbamoylimino)-5pentylsulphi nyl-1,3,4-thi adi azoli n-3-i de
Potassium salt of 2-(dimethylcarbamoylimino)-5pentylsulphinyl-1,3,4-thi adi azoli n-3-i de
Lithium salt of 2-(dimethylcarbamoylimino)-525 pentylsulphinyl-1,3,4-thiadiazolin-3-ide
Physical Constant
M.p. 191°C (decomposition)
M.p. 178°C (decomposition)
M.p. 193°C (decomposition)
M.p. 200°C (decomposition)
M.p. 250°C
M.p. 250°C
M.p. 248°C
M.p. 250°C
M.p. 250°C
M.p. 226°C (decomposition)
M.p. 176°C (decomposition)
M.p. 174°C (decomposition)
- 12 4 4 5 6 5
Name of the Compound
Sodium salt of 2-(dimethylcarbamoylimino)-5 hexylsulphony!-1,3,4-thiadi azoli n-3-i de
Lithium salt of 2-(dimethylcarbamoylimino)-55 isopropylthio-1,3,4-thiadiazolin-3-ide
Lithium salt of 2-(dimathylcarbamoy1inrino)-5(2-methyl-2-propeny1thi o)-1,3,4-thi adiazolin-3-ide
Sodium salt of 2-(dimethylcarbamoylimino)-510 isobutylthio-1,3,4-thiadiazolin-3-ide
Potassium salt of 2-(dimethylcarbamoylimino)-5isobutylthio-1,3,4-thiadiazolin-3-ide
Sodium salt of 2-(dimethylcarbamoylimino)-5isopropylsulphony!-1,3,4-thiadiazolin-3-ide
Potassium salt of 2-(dimethylcarbamoylimiho)-5isopropylsulphonyl-1,3,4-thiadiazolin-3-ide
Sodium salt of 2-(dimethylcarbamoylimino)-5isopropylsulphinyl-1,3,4-thiadiazolin-3-ide
Potassium salt of 2-(dimethylcarbamoylimino)-520 isopropylsulphinyl-1,3,4-thiadiazolin-3-ide
Lithium salt of 2-(dimethylcarbamoylimino)-5isopropylsulphinyl-1,3,4-thiadiazolin-3-ide
Lithium salt of 2-(dimethylcarbamoylimino)-5propylsulphonyl-1,3,4-thiadiazolin-3-ide
Lithium salt of 2-(dimethylcarbamoylimino)-5isobutylsulphony!-1,3,4-thiadiazolin-3-ide
Physical Constant
M.p. 215°C (decomposition)
M.p. >250°C
M.p. 250°C (decomposition)
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. 247°C (decomposition)
M.p. 240°C (decomposition)
M.p. 245°C (decomposition)
M.p. 25O°C (decomposition)
M.p. 175°C (decomposition)
- 13 Name of the Compound
Lithium salt of 2-(dimethylcarbamoylimino)-5pentylthio-1,3,4-thiadiazolin-3-ide
Lithium salt of 2-(dimethylcarbamoylimino)-5i sobutylthi o-l,3,4-thi adi azoli n-3-i de
Lithium salt of 2-(dimethylcarbarnoylimino)-5propylthi o-l,3,4-thi adi azoli n-3-i de
Sodium salt of 2-(dimethylcarbamoylimino)-5propylsulphony!-1,3,4-thi adi azoli n-3-ide
Lithium salt of 2-(dimethylcarbamoylimino)-5i sopropyl sulphony1-1,3,4-thi adi azoli n-3-ide
Sodium salt of 2-(dimethyl carbamoylimino)-5isobutylsulphonyl-1,3,4-thiadiazolin-3-ide
Potassium salt of 2-(dimethylcarbamoylimino)-5i sobutylsulphonyl-1,3,4-thi adi azoli n-3-i de Potassium salt of 2-(dimethylcarbamoylimino)-5pentylthi o-l,3,4-thi adi azoli n-3-i de Sodium salt of 2-(dimethylcarbamoylimino)-5pentylthi o-l,3,4-thi adi azoli n-3-ide Potassium salt of 2-(dimethylcarbamoylimino)-5propyl sul phonyl-1,3,4-thi adiazol.i n-3-i de Sodium salt of 2-(dimethylcarbamoylimino)-5pentylsulphonyl-1,3,4-thiadi azoli n-3-i de Potassium salt of 2-(dimethylcarbamoylimino)-5pentylsulphony!-1,3,4-thi adi azoli n-3-i de
Physical Constant
M.p. 260°C (decomposition)
M.p. >250°C
M.p. 263°C (decomposition)
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >250°C
M.p. >25D°C
M.p. >250°C
M.p. >250°C
M.p. 240°C (decomposition)
M.p. 230°C (decomposition)
- 14 Name of the Compound
Sodium salt cf 2-(dimethylcarbamoylimino)-5propyTsui phi nyl-1,3,4-thi adi azoli n-3-i de Lithium salt of 2-(dimethylcarbamoylimino)-5propy1sulphi nyl-1,3,4-thi adiazoli n-3-i de Lithium salt of 2-(dimethylcarbamoylimino)-5hexylsulphonyl-1,3,4-thiadi azoli n-3-i de
Physical Constant
M.p. 256°C (decomposition)
M.p. 228°C (decomposition)
M.p. 158°C (decomposition)
The compounds of the present invention are colourless and odourless, crystalline substances, which are excellently soluble in water, are readily soluble in polar organic solvents, for example carboxylic acid amides, for example dimethylformamide, sulphoxides, for example dimethyl sulphoxide, and lower alcohols, for example methanol and ethanol, are less soluble in carbonitriles, for example acetonitrile, and are insoluble in hydrocarbons, halogenated hydrocarbons, ethers and ketones.
The following Examples illustrate the invention. Examples 1 and 2 illustrate the manufacture of compounds of the general formula I and Examples 3 to 5 illustrate the mode of action of the compounds of the general formula I.
Example 1
Potassium Salt of 5 - ethylthio- 2 - (dimethylcarbamoylimino) - 1,3,4thiadiazolin-3-ide
To a suspension of 30.3 grams of 5 - ethylthio - 2 - (dimethylcarbamoylimino) - 1,3,4 - thiadiazolin - 3 - carboxylic acid dimethylamide (M.p.: 91°C) in 200 ml of methanol were added dropwise at room temperature, while stirring, 6.58 grams of potassium hydroxide of 85% strength, dissolved in 100 ml of methanol.
The reaction mixture after standing overnight, was dried in vacuo, and the residue remaining behind was digested twice with isopropanol and dried in vacuo.
Yield: 25.2 grams (93.4% of the theoretical yield)
M.p.: >250°C
Analysis: Calculated: C 31.09% H 4.10% N 20.72% K 14.46%
Found: C 30.89% H 4.31% N 20.43% K 14.72%
Example 2
Sodium Salt of 2 - (dimethylcarbamoylimino) - 5 - methylsulphonyl10 1,3,4 - thiadiazolin - 3 - ide
12.5 grams of 1,1 - dimethyl -3-(5- methyl sulphonyl - 1,3,4thiadiazol -2-yl) - urea were suspended in 150 ml of methanol, and at room temperature a solution of 2 grams of sodium hydroxide in 100 ml of methanol was slowly added while stirring.
After standing for 2 hours, the solvent was distilled off in vacuo and the residue was first washed twice with 50 ml of isopropanol, then with di isopropyl ether and dried in vacuo.
Yield: 12.6 grams (92.7% of the theoretical yield)
M.p.: >250°C
Analysis: Calculated: C 26.47% H 3.33% N 20.58% Na 8.44%
-Found: C 26.49% H 3.38% N 20.41% Na 8.49%
Each of the other compounds of the present invention listed in the Table above can be prepared in a manner analogous to that described in Example 1 or 2.
- 16 •1 4 S ϋ S
Example 3
In a series of tests carried out in a greenhouse the compounds of the present invention listed in the Table below were each sprayed at a rate of application of 5 kg of active substance per hectare, dissolved in 500 litres of water per hectare, on mustard and tomatoes as test plants by the pre- and post-emergence methods. Three weeks after the treatment the results of the treatment were evaluated, the results being expressed by a numerical scale extending from 1 to 4, the value 0 representing no action and the value 4 representing destruction of the plants. As can be seen from the was generally achieved.
Compound of the Present Invention
Sodium salt of 2-(dimethylcarbamoyli mino)-5-propylthi ΟΙ ,3,4-thiadiazolin-3-ide
Potassium salt of 2-(dimethylcarbamoylimino)-5-propylthi o1.3.4- thiadi azoli n-3-ide
Potassium salt of 5-ethylthio-2(d i methyl carbamoyli mi no) -1,3,4thiadiazolin-3-ide
Potassium salt of 2-(dimethylcarbamoy1i mino)-5-methylthi o1.3.4- thiadiazolin-3-ide
Potassium salt of 5-ethylsulphony1-2-(di methyl carbamoylimino)-!,3,4-thiadi azoli n-3-ide
Table destruction of the test plants Pre-Emergence Mustard Tomato Post-Emergence Mustard Tomato 4 4 4 4 4 4 4 4 4 2 4 4 4 4 4 4 4 4 4 4
- 17 4 4 S β 5
Compound of the Present Invention Pre-Emergence Post-Emergence Mustard Tomato Mustard Tomato Sodium salt of 2-(dimethyl- 4 4 4 4 carbamoylimi no)-5-methyl- sulphonyl-1,3,4-thiadiazolin- 3-ide Sodium salt of 5-ethylthio-2- 4 4 4 4 (di methyl carbamoylimi no)- 1,3,4-thiadiazolin-3-ide Sodium salt of 2-(dimethyl- 4 4 4 4 carbamoylimi no)-5-methylthi o- 1,3,4-thiadiazolin-3-ide Sodium salt of 5-butylthio-2- 4 4 4 4 (di methyl carbamoyli mi no)- 1,3,4-thi adi azoli n-3-i de Sodium salt of 5-ethylsulphonyl - 4 4 4 4 2-(dimethyl carbamoylimi no)- 1,3,4-thiadiazolin-3-ide Potassium salt of 2-(dimethyl- 4 4 4 4 carbamoylimi no)-5-methyl- sulphonyl-1,3,4-thiadiazolin- 3-ide Sodium salt of 2-(dimethylcarba- 4 4 4 4
moylimino)-5-methylsulphi nyl1,3,4-thiadiazolin-3-ide
- 18 4 4 5 « 5
Compoud of the Pre-Emergence Post-Emergence Present Invention Mustard Tomato Mustard Tomato Potassium salt of 2-(dimethyl- carbamoyl i mi r.o) -5-methyl - sulphinyl-1,3,4-thiadiazolin- 3-ide 4 4 4 4 Sodium salt of 2-(dimethyl- carbamoy1i mi no)-5-(2-propynyl- thio)-l,3,4-thiadiazolin- 3-ide 4 4 4 4 Potassium salt of 2-(dimethyl- carbaniovl imi no)-5-(2-propynyl - tnio)-l,3,4-thiadiazolin- 3-ide 4 4 4 4 Lithium salt of 5-ethylthio-2- (dimethylcarbamoylimino)- 1,3,4-thiadiazolin-3-ide 4 4 4 4 Lithium salt of 2-(dimathyl- carbamoy1imino)-5-methylthio- 1,3,4-thiadiazolin-3-ide 4 4 4 4 Sodium salt of 2-(dimethyl- carbamoylimino)-5-isopropylthio- 1,3,4-thiadiazolin-3-ide 4 4 4 4 Potassium salt of 2-(dimethyl- carbamoylimino)-5-isopropylthi o- 1,3,4-thi adi azoli n-3-i de - 19 4 4 4 4
Compound of the Pre-Line rgence I’os t-f mergence Present Invention Mustard Ionia to Musi aril Ionia to Potassium sal t of b-butylthio- 2-(dimethyl carbamoylimino)- 1,3,4-thiadiazolin-3-ide 4 4 4 4 Sodium salt of 2-(dimethyl- carbamoylimi no)-5-(2-methyl- 2-propenylthio)-l,3,4-thiadiazol ϊη-3-ide 4 4 4 4 Potassium salt of 2-(dimethyl- carbamoylimi no)-5-(2-methyl- 2-propeny1thi o)-1,3,4-thi a- diazolin-3-ide 4 4 4 4 Potassium salt of 2-(dimethyl- carbamoylimino)-5-hexylsulphonyl- 1,3,4-thiadiazolin-3-ide 4 4 4 4 Sodium salt of 2-(dimethyl- carbamoylimi no)-5-hexy1sulphi nyl- 1,3,4-thiadiazolin-3-ide 4 4 Potassium salt of 2-(dimethy1- carbamoylimi no)-5-hexylsulphi nyl- 1,3,4-thiadiazolin-3-ide 4 4 4 Lithium salt of 2-(dimethyl- carbamoylimi no)-5-hexylsulphi nyl- 1,3,4-thiadiazolin-3-ide 4 3 4 3
- 20
Compound of the Present Invention Pre-Emergence Post-Emergence Mustard Tomato Mustard Tomato Lithium salt of 2-(dimethyl- carbamoylimi no)-5-isopropyl- thio-l,3,4-thiadiazolin-3-ide 4 4 4 4 Lithium salt of 2-(dimethyl- carbamoyli mino)-5~(2-methyl -2- propenylthio)-! ,3,4*-thiadi- azolin-3-ide 4 4 4 4 Sodium salt of 2-(dimethyl- carbamoy1imi no)-5-isobutyl- t.hio-l,3,4-thiadiazo1in-3-ide 4 4 4 4 Potassium salt of 2-(dimethyl- carbamoylimino)-5-isobutyl- thio-1,3,4-thiadiazolin-3-ide 4 4 4 4 Sodium salt of 2-(dimethyl- carbamoyli mino-5-i sopropyl- su!phonyl-l,3,4-thiadiazolin- 3-ide 4 4 4 4 Potassium salt of 2-(dimethyl- carbamoylirai no)-5-i sopropyl- sulphonyl-1,3,4-thiadiazolin- 3-ide 4 4 4 4 Sodium salt of 2-(dimethylcarba- 4 4 4 4
moyl ΐ mi no)-5-i sopropyl s u 1 phi nyl 1,3,4-thiadia2olin-3-ide
- 21 4 4SCS
Compound of tin' Pro- l.iiiorgi'iiie Post.-I moryi’ine Present Invention Mustard tomato Mustard Toma to Potassium salt of 2-(dimethyl- carbamoylimi no)-5-isopropyl- sulphinyl-1,3,4-thiadiazolin- 3-ide 4 4 4 4 Lithium salt of 2-(dimethyl- carbamoylimi no)-5-i sopropyl- sulphinyl-1,3,4-thiadiazolin- 3-ide 4 4 4 4 Lithium salt of 2-(dimethyl- carbamoylimi no)-5-propylsul- phonyl-1,3,4-thiadiazolin- 3-ide 4 4 4 4 Lithium salt of 2-(dimethy1 carbamoylimino)-5-pentylthio- 1,3,4-thiadi azoli n-3-i de 4 4 4 4 Lithium salt of 2-(dimethyl- carbamoylimi no)-5-i sobutylsul- phony1-1,3,4-th i ad i azoli n-3-i de 4 4 4 4 Lithium salt of 2-(dimethyl- carbamoylimi no)-5-isobuty1thi o- 1,3,4-thiadiazolin-3-ide 4 4 4 4 Lithium salt of 2-(dimethyl- carbamoy1imi no)-5-propylth i o- 1,3,4-thiadiazo1in-3-ide 4 4 4 4
•14 5 6 5
Compound of the Pre-Emergence Post-Emergence Present Invention Mustard Tomato Mustard Tomato Sodium salt of 2-(dimethyl- carbamoy1 imino)-5-propy1 sulphonyl-! ,3,4-thiadiazolin- 3-ide 4 4 4 4 Lithium salt of 2-(dimethyl- carbamoylimi no}-5-i sopropyl- sulphonyl-1,3,4-thiadiazolin- 3-ide 4 4 4 4 Sodium salt of 2-(dimethyl- carbamoylimi no)-5-i sobutylsul- phonyl-1,3,4-thi adi azoli n-3-i de 4 4 4 4 Potassium salt of 2-(dimethyl- carbamoy1imino)-5-isobutyl- sulphonyl-1,3,4-thiadiazolin- 3-ide 4 4 4 4 Potassium salt of 2-(dimethyl- carbamoylimi no)-5-penty1thi ΟΙ ,3,4-thiadiazolin-3-ide 4 4 4 4 Sodium salt of 2-(dimethyl- carbamoylimino)-5-pentylthio- 1,3,4-thiadiazolin-3-ide 4 4 4 4 Potassium salt of 2-(dimethyl- carbamoylimi no)-5-propy1 sulphonyl -1 ,3,4-thiadi azoli n-3-ide 4 4 4 4
Compound of the Present Invention
Sodium salt of 2-(dimethylcarbamoylimino)-5-pentyl-su1phonyl-1,3,4-thi adi azoli n-3-i de
Potassium salt of 2-(dimethylcarbamoylimino)-5-penty1 sulphonyl -1,3,4-thi adi azoli n-3-ide
Lithium salt of 2-(dimethylcarbamoylimi no)-5-i sobutylsulphi nyl 1.3.4- thi adi azoli n-3-i de
Lithium salt of 2-(dimethylcarbamoylimi no)-5-penty1 sulphonyl1.3.4- thiadiazolin-3-ide
Sodium salt of 2-(dimethylcarbamoyl imi no)-5-isobuty1 sul phi nyl1.3.4- thiadiazo1in-3-ide
Potassium salt of 2-(dimethylcarbaffloylimino)-5-isobutylsulphinyl-1,3,4-thiadiazolin3-ide
Lithium salt of 2-(dimethylcarbamoylimino)-5-hexylthio1.3.4- thiadiazolin-3-ide
Sodium salt of 2-(dimethy1carbamoylimi no)-5-hexylthi o1.3.4- thiadiazoli n-3-i de
Pre-Emergence Mustard Tomato Post-Emergence Mustard Tomato 4 4 4 4 4 4 4 4 4 4 4 4 4 — 4 4 4 4 4 4 4 4 4 4 — — 4 4 4 4
- 24 4 ii 5 S 5
Compound of the Present Invention Pre-Emergence Post-Emergence Mustard Tomato Mustard Tomato Potassium salt of 2-(dimetbyl- carbamoyl imi no)-5-hexyIthi o- I,3,4-thiadiazolin-3-ide 4 4 Sodium salt of 2-(dimethyl- carbamoylimino)-5-pentylsul- phinyl-1,3,4-thisdiazolin-3-ide 4 4 Potassium salt of 2-(dimethyl- carbamoylimi no)-5-pentyl- sulphi nyl-1,3,4-thi adi azoli n- 3-ide 4 4 Lithium salt of 2-(dimethyl- carbamoylimi no)-5-pentyl- sulphinyl-1,3,4-thiadiazolin- 3-ide 4 4 Sodium salt of 2-(dimethyl- carbamoylimi no)-5-hexy1- sulphonyl-1,3,4-thiadiazolin- 3-ide 4 4 Sodium salt of 2-(dimethyl- carbamoylimino)-5-propyl - sulphinyl-1,3,4-thiadiazolin- 3-ide 4 4 4 4 Lithium salt of 2-(dimethyl- carbamoylimino)-5-propylsulphi nyl-1,3,4-thi adiazoli n-3-i de - 25 4 4 4 4
Example 4
In n serins of tests mrriod out in a qieeniiiiuse the planls listed in the following table were treated before tlieir emergence witn the listed agents being tested at the rates of application given. For this purpose the agents were in each case applied uniformly to the soil in the form of an aqueous solution using 1 kg of active substance per hectare with 500 litres of water per hectare. The results shot·/ that the compounds of the present invention, in contradistinction to the known compounds used for comparison, have a good selectivity. The results are expressed by a numerical scale extending from 0 to 10, the value 0 representing destruction of the plant and the value 10 representing no damage.
- 26 •i 4 5 6 3 ssue
Boiieqi. Busqas iiqsB snjo Boiipouiipg sapiojnsoXui srunosdotv snxaipuqeu snqquBdBiuv snuE/to B3JnE}U33
3|ne3Lxa|duiB tunLuneq uinqgSss lunuraqquEsAxqo Bauncur-d eaoaodT en.uuoaeip eueouqew
SlJBSinA 0133U3S
Bipaiil BUBLI33S sunqBuos ia
3ZLBW
E3d
UBaq-qsng
Bij/BouBqsqns sApos jo Bq ω
ίο, c □
o
o.
Ξ σ
δ o
ία.
co
I c
χ= ε co t
c
Ό o
v>
o •p
JO
Sto
is TJ nJ E σ re r— Ό «Γ~ rd w nJ in >> rc •p* r~ JZ •r“ >, E >, x: E -P x: O •P 13 O -p 3 Φ •p E 1 *r* E I •r* E 1 fO «^· cn ra <- Vi XI tn XI Λ in XJ * i- co 5- CO nJ CO re •p rc * -P 1 »> u r— o u r— O CM *—
•p r— re carbamoylimi no)-5-methylthio- 27 445SS ssuadoieq uinqSuos
B3ll®4.L eusqas l l LhS snuo bo iqoou 11433 sapiounsoAui snunaadoiv snxaijouqau sniiquEUBiuv snueAa Eaunequag aine3i.xa|dujs uintiuBq umqaBas mniuaqquBsAuqg eaandund saoSodi e l t Luiouieqa BUBaJipw
ΤΰΕβμΪΛ OLaauas
BLpaut BUBLiais uinq6jos aa ly az lew say
OTEgoy qnu-punojg
UBaq-qsng
Bq/aauBgsqns aappe 30 By o
destruction of the plant no damage
4 5 6 5
Example 5
In a series of tests carried out in a greenhouse the plants listed in the following Table were treated after their emergence with the listed agents being tested at a rate of application of 1 kg of active substance/hectare. For this purpose the agents were in each case sprayed uniformly over the plants in the form of an aqueous solution using 500 litres of water per hectare. Also in this case the compound of the present invention exhibited 3 weeks after the treatment a high selectivity coupled with an excellent action against the weeds. The agent usee) for comparison did not exhibit selectivity. Again, the results are expressed by a numerical scale extending from 0 to 10, the value 0 representing destruction of the plant and the value 10 representing no damage.
- 29 44S65 eoiieit. Btaaqas Baandand eaourodi uingaSas uiniuaqquGsX'u'Oo a'uLaisde uinL[eg snxauoaqaa snqquaaBiuv snueXo eaanequag
3LnB3i.xa[duiB uiniiusi B[[LlilOUIBtp BiaBoTaqBW siaeBinA oioauas
Bipaui Bi.aBi.iais uinqBaos ao aziBH
Baa b/Cos oq.B}Od qnu-punoag
SCL
04 1 1 1 ) o 04 O <—>» φ ί •r- ο -σ C o r~ x: C o 3 O 4J ι (/) r— N f— ε CO •r- 4- (O >J ·Γ“ 1 S- •|~ 44 C ΓΟ S- •o 3 >> »»“ CL 44 «3 X) Ο τ— ε 1 •ι- 1 ε Ο o LO J= LO ro Ν o x_^ 44 an Π3 1 1 4- s- •ρ» s- r-~ «d* o <α Ό o i υ to 4- r— CO 4J r— *r* >> n γ- >> JZ 44 JZ r— re π} _c 44 C 44 I Φ (/) +4 1 Φ Φ r~ U Φ <4* CD ε >i 3 £ ε fl < •r— zz I 3 CO Ό 44 ’Γ n t Φ r*“ -σ r“ 00 ε >> ο λ ςη r—
-σ
Claims (15)
1. ,3,4 - thiadiazolin - 3 - ide. 65. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - hexylsulphonyl - 1,3,4 - thiadiazolin - 3 - ide. 66. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - hexyl10 sulphonyl - 1,3,4 - thiadiazolin - 3 - ide. 67. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - hexylsulphinyl - 1,3,4 - thiadiazolin - 3 - ide. 68. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - hexylsulphinyl - 1,3,4 - thiadiazolin - 3 - ide. 15 69. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - hexylsulphinyl - 1,3,4 - thiadiazolin - 3 - ide. 70. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - isobutylthio - 1,3,4 - thiadiazolin - 3 - ide. 71. A herbicidal preparation which comprises a compound of the 20 general formula I given in claim 1, in which R, B and £ have the meanings given in claim 1, in admixture or conjunction with a suitable carrier. 72. A herbicidal preparation which comprises a compound as claimed in any one of Claims 2 to 6, in admixture or conjunction with a suitable carrier. 25 73. A herbicidal preparation which comprises the compound claimed in any one of Claims 7 to 29, in admixture or conjunction with a suitable carrier. - 36 4 4 5 6 5 74. A herbicidal preparation which comprises the compound claimed in any one of Claims 30 to 70, in admixture or conjunction with a suitable carrier. 75. A preparation as claimed in any one of Claims 71 to 74, which is 5 in the form of a powder, a strewable preparation, granules, a solution, an emulsion or a suspension. 76. A preparation as claimed in any one of Claims 71 to 75, containing a single compound of the general formula I in an amount of 10 to 80% by weight. 1,3,4 - thiadiazolin - 3 - ide. 19. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - methylsulphinyl - 1,3,4 - thiadiazolin - 3 - ide. 20 20. Potassium salt of 5 - butylthio - 2 - (dimethylcarbamoylimino) 1,3,4 - thiadiazolin - 3 - ide. 21. Lithium salt of 5 - butylthio - 2 - (dimethylcarbamoylimino) 1,3,4 - thiadiazolin - 3 - ide. 22. Sodium salt of 2 - (dimethylcarbamoylimino) -5-(2- propynyl25 thio) - 1,3,4 - thiadiazolin - 3 - ide. - 32 1 J 5 6 S 23. Potassium salt of 2 - (dimethylcarbamoyl imino) -5-(2- propynylthio) - 1,3,4 - thiadiazolin - 3 - ide. 24. Lithium salt of 5 - ethylthio - 2 - (dimethylcarbamoylimino) 1,3,4 - thiadiazolin - 3 - ide. 25. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - methylthio1,3,4 - thiadiazolin - 3 - ide. 26. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - isopropylthio1,3,4 - thiadiazolin - 3 - ide. 27. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - isopropylthio - 1,3,4 - thiadiazolin - 3 - ide. 28. Sodium salt of 2 - (dimethylcarbamoylimino) -5-(2- methyl 2 - propenylthio) - 1,3,4 - thiadiazolin - 3 - ide. 29. Potassium salt of 2 - (dimethylcarbamoylimino) -5-(2- methyl 2 - propenylthio) - 1,3,4 - thiazolin - 3 - ide. 30. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - isopropylthio - 1,3,4 - thiadiazolin - 3 - ide. 31. Lithium salt of 2 - (dimethylcarbamoylimino) -5-(2- methyl2 - propenylthio) - 1,3,4 - thiadiazolin - 3 - ide. 32. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - isobutylthio1,3,4 - thiadiazolin - 3 - ide. 33. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - isopropylsulphonyl - 1,3,4 - thiadiazolin - 3 - ide. 34. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - isopropylsulphonyl - 1,3,4 - thiadiazolin - 3 - ide. 35. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - isopropylsulphinyl - 1,3,4 - thiadiazolin - 3 - ide. - 33 36. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - isopropylsulphinyl - 1,3,4 - thiadiazolin - 3 - ide. 37. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - isopropylsulphinyl - 1,3,4 - thiadiazolin - 3 - ide. 38. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - propylsulphonyl1,3,4 - thiadiazolin - 3 - ide. 39. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - isobutylsulphonyl - 1,3,4 - thiadiazolin - 3 - ide. 40. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - pentylthio 1,3,4 - thiadiazolin - 3 - ide. 41. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - isobutylthio 1,3,4 - thiadiazolin - 3 - ide. 42. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - propylthio 1,3,4 - thiadiazolin - 3 - ide. 43. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - propylsulphonyl1,3,4 - thiadiazolin - 3 - ide. 44. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - isopropylsulphonyl - 1,3,4 - thiadiazolin - 3 - ide. 45. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - isobutylsulphonyl - 1,3,4 - thiadiazolin - 3 - ide. 46. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - isobutylsulphonyl - 1,3,4 - thiadiazolin - 3 - ide. 47. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - pentylthio 1,3,4 - thiadiazolin - 3 - ide. 48. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - pentylthio 1,3,4 - thiadiazolin - 3 - ide. - 34 4 4 5 S 5 49. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - propylsulphonyl - 1,3,4 - thiadiazolin - 3 - ide. 50. Sodium salt of 2 - (dimethyl carbamoyl imino) - 5 - pentyl sulphonyl 1,3,4 - thiadiazolin - 3 - ide. 51. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - pentylsulphonyl - 1,3,4 - thiadiazolin - 3 - ide. 52. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - propylsulphinyl1,3,.4 - thiadiazolin - 3 - ide. 53. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - propylsulphinyl1,3,4 - thiadiazolin - 3 - ide. 54. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - isobutylsulphinyl - 1,3,4 - thiadiazolin - 3 - ide. 55. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - pentylsulphonyl - 1,3,4 - thiadiazolin - 3 - ide. 56. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - isobutylsulphinyl - 1,3,4 - thiadiazolin - 3 - ide. 57. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - isobutylsulphinyl - 1,3,4 - thiadiazolin - 3 - ide. 58. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - hexylthio 1,3,4 - thiadiazolin - 3 - ide. 59. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - hexylthio 1,3,4 - thiadiazolin - 3 - ide. 50. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - hexylthio 1,3,4 - thiadiazo!in-3-ide. 61. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - pentylsulphinyl1,3,4 - thiadiazolin - 3 - ide. - 35 \_ 62. Potassium salt of 2 - (dimetliylcarbanioylimino) - 5 - pentylsulphinyl - 1,3,4 - thlndlazo) in - .1 - ide. 63. Lithium salt of 2 - (dimethylcarbamoylimino) - 5 - pentyl sulphinyl - 1,3,4 - thiadiazolin - 3 - ide. 1,3,4 - thiadiazolin - 3 - ide. 1,3,4 - thiadiazolin - 3 - ide.
2. A compound as claimed in Claim 1, wherein R represents an alkyl group containing 1 to 6 atoms.
3. A compound as claimed in Claim 1, wherein R represents an alkenyl group containing up to 6 carbon atoms.
4. A compound as claimed in Claim 1, wherein R represents an alkynyl group containing up to 6 carbon atoms. 5. Of the general formula VI (VI) in which R and ji have the meanings given above, is reacted with a metal compound of the general formula V BY (V) 5 is reacted in the presence of an acid-binding agent with a 1,3,4 - thiadiazolylamine of the general formula III N-N R-S(O) -C C -NH, n \ / z s' (III) in which R and £ have the meanings given above, to form a 2 - (dimethylcarbamoylimino) - 1,3,4 - thiadiazolin - 3 - carboxylic acid dimethylamido 5 an amount within the range of from 1 to 5 kg per hectare. 96. A method as claimed in any one of Claims 90 to 94, wherein two or more compounds of the general formula I are used for the treatment in a total amount within the range of from 1 to 5 kg per hectare. 97. A method as claimed in any one of Claims 90 to 96, wherein the 5 64. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - hexyl sulphonyl ·
5. A compound as claimed in any one of Claims 1 to 4, wherein B represents an alkali metal atom.
6. A compound as claimed in Claim 5, wherein the alkali metal atom is a lithium, sodium or potassium atom.
7. Potassium salt of 5 - ethylthio - 2 - (dimethylcarbamoylimino) 1,3,4 - thiadiazolin - 3 - ide.
8. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - methylsulphonyl
9. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - propylthio1,3,4 - thiadiazolin - 3 - ide. 10. In which B and Y have the meanings given above. 104. A process as claimed in Claim 103, wherein each step is carried out in the presence of a solvent. 105. A process as claimed in Claim 103, conducted substantially as described herein. 10 derivative of the general formula IV /h 3 .CO-N ’N R-S(O) n -C, \ /¼ / CH ' 3 \ S Z N-co-rZ \h 3 (iv) in which R and £ have the meanings given above, which is split with a metal compound of the general formula V - 40 4 4 5 6 5 in which B has the meaning given above and Y represents a hydrogen atom or a hydroxyl, Cj—C 3 - alkoxy or amino group, or (b) a 1 - (1,3,4 - thiadiazol - 2 - yl) - 3,3 - dimethylurea derivative 10 crop is a bush-bean, ground-nut, potato, pea, rice, maize, sorghum or soya crop. 98. A method of protecting a waste land against weeds, wherein a waste land is treated with one or more compounds of the general formula I given in Claim 1, in which R, β and n have the meanings given in Claim 1, 15 the compound(s) being used in a total amount cf more than 5 kg per hectare. 99. A pack which comprises a compound of the general formula I given in Claim 1, in which R, B and n. have the meanings given in Claim 1, together with instructions for its use as a selective herbicide. 100. A pack which comprises a compound as claimed in any one of 20 Claims 2 to 6 together with instructions for its use as a selective herbicide. 101. A pack which comprises the compound claimed in any one of Claims 7 to 29 together with instructions for its use as a selective herbicide. 25 102. A pack which comprises the compound claimed in any one of Claims 30 to 70 together with instructions for its use as a selective herbicide. - 39 •14 5 6 5 103. A process for the manufacture of a compound of the general formula I given in Claim 1, in wlii.ih II, |i and n have the menntnir· given in Claim 1, wherein (a) dimethylcarbamoyl chloride of the formula II H 3 C N—CO—Cl (II) Z H 3 C 10 77. A preparation as claimed in any one of Claims 71 to 75, containing two or more compounds of the general formula I in a total ' amount of 10 to 80% by weight. 78. A preparation as claimed in any one of Claims 71 to 77, containing a single surface-active agent in an amount of up to 20% by weight. 15 79. A preparation as claimed in any one of Claims 71 to 77, containing two or more surface-active agents in a total amount of up to 20% by weight. 80. Any one of the herbicidal preparations as claimed in Claim 71 and substantially as described in Example 3 herein, 20 81. Any one of the herbicidal preparations as claimed in Claim 71 and substantially as described in Examples 4 and 5 herein. 82. A method of protecting a living plant against weeds, wherein the area in the vicinity of a living plant is treated with a compound of the general formula I given in Claim 1, in which R, B and n have the 25 meanings given in Claim 1. - 37 1 j Η 6 ft HJ. A melhuil as. i.laImeil in Claim H?, wherein the area is. tieated with a compound as claimed in any one of Claims 2 to 6. 84. A method as claimed in Claim 82, wherein the area is treated with the compound claimed in any one of Claims 7 to 29. 85. A method as claimed in Claim 82, wherein the area is treated with the compound claimed in any one of Claims 30 to 70. 86. A method as claimed in Claim 82, wherein the area is treated with a herbicidal preparation as claimed in any one of Claims 71 to 81. 87. A method as claimed in any one of Claims 82 to 86, wherein a single compound of the general formula I is used for the treatment in an amount within the range of from 1 to 5 kg per hectare. 88. A method as claimed in any one of Claims 82 to 86, wherein two or more compounds of the general formula I are used for the treatment in a total amount within the range of from 1 to 5 kg per hectare. 89. A method as claimed in Claim 82, conducted substantially as described in Example 4 or 5 herein. 90. A method of protecting a crop area against weeds, wherein a crop area is treated with a compound of the general formula I given in Claim 1, in which R, B and £ have the meanings given in Claim 1. 91. A method as claimed in Claim 90, wherein the crop area is treated with a compound as claimed in any one of Claims 2 to 6. 92. A method as claimed in Claim 90, wherein the crop area is treated with the compound claimed in any one of Claims 7 to 29. 93. A method as claimed in Claim 90, wherein the crop area is treated with the compound claimed in any one of Claims 30 to 70. 94. A method as claimed in Claim 90, wherein the crop area is - 38 >4565 treated with a herbicidal preparation as claimed in any one of Claims 71 to SI. 95. A method as claimed in any one of Claims 90 to 94, wherein a single compound of the general formula I is used for the treatment in 10 15. Sodium salt of 5 - butylthio - 2 - (dimethylcarbamoylimino) 1,3,4 - thiadiazolin - 3 - ide. 16. Sodium salt of 5 - ethylsulphony! - 2 - (dimethylcarbamoylimino)1,3,4 - thiadiazolin - 3 - ide. 17. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - methyl15 sulphonyl - 1,3,4 - thiadiazolin - 3 - ide. 18. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - methylsulphinyl
10. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - propylthio- 31 4456S
11. Potassium salt of 2 - (dimethylcarbamoylimino) - 5 - methylthio - 1,3,4 - thiadiazolin - 3 - ide.
12. Potassium salt of 5 - ethyl sulphonyl - 2 - dimethyl carbamoyl5 imino) - 1,3,4 - thiadiazolin - 3 - ide.
13. Sodium salt of 5 - ethylthio - 2 - (dimethylcarbamoylimino) 1,3,4 - thiadiazolin - 3 - ide.
14. Sodium salt of 2 - (dimethylcarbamoylimino) - 5 - methylthio 1,3,4 - thiadiazolin - 3 - ide.
15. 105. A process as claimed in Claim 103, conducted substantially as described in Example 1 or 2 herein.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762607481 DE2607481A1 (en) | 1976-02-20 | 1976-02-20 | 2-DIMETHYLCARBAMOYLIMINO-1,3,4-THIADIAZOLIN-3-ID DERIVATIVES, PROCESS FOR THE PREPARATION OF THESE COMPOUNDS AND HERBICIDAL AGENTS THESE CONTAINED |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE44565L IE44565L (en) | 1977-08-20 |
| IE44565B1 true IE44565B1 (en) | 1982-01-13 |
Family
ID=5970729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE346/77A IE44565B1 (en) | 1976-02-20 | 1977-02-18 | Herbicidally active 2-dimethylcarbomoylimino-1,3,4-thiadiazolin-3-ide derivatives, process for their manufacture and their use |
Country Status (32)
| Country | Link |
|---|---|
| JP (1) | JPS52102277A (en) |
| AR (1) | AR217638A1 (en) |
| AT (1) | AT351314B (en) |
| AU (1) | AU2186377A (en) |
| BE (1) | BE851600A (en) |
| BG (1) | BG27713A3 (en) |
| BR (1) | BR7700890A (en) |
| CA (1) | CA1077044A (en) |
| CS (1) | CS193083B2 (en) |
| DD (1) | DD128655A5 (en) |
| DE (1) | DE2607481A1 (en) |
| DK (1) | DK29577A (en) |
| EG (1) | EG12458A (en) |
| ES (1) | ES456051A1 (en) |
| FI (1) | FI770452A (en) |
| FR (1) | FR2341573A1 (en) |
| GB (1) | GB1577523A (en) |
| GR (1) | GR62395B (en) |
| IE (1) | IE44565B1 (en) |
| IL (1) | IL51461A (en) |
| IN (1) | IN155287B (en) |
| IT (1) | IT1118003B (en) |
| LU (1) | LU76741A1 (en) |
| NL (1) | NL7701752A (en) |
| NZ (1) | NZ183378A (en) |
| PL (1) | PL101774B1 (en) |
| PT (1) | PT66210B (en) |
| RO (1) | RO73052A (en) |
| SE (1) | SE7701776L (en) |
| SU (2) | SU648098A3 (en) |
| TR (1) | TR20545A (en) |
| ZA (1) | ZA77985B (en) |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3565901A (en) * | 1969-01-29 | 1971-02-23 | Air Prod & Chem | Certain salts of 1,3,4-thiadiazol-2-ylureas |
| GB1290223A (en) * | 1969-04-21 | 1972-09-20 | ||
| CH554886A (en) * | 1970-01-15 | 1974-10-15 | Air Prod & Chem | Herbicidal and fungicidal 1-(1,3,4-thiadiazol-2-yl)-3-substd. ureas - prepd. from 2-amino-5-substd.-1,3,4-thiadiazoles and N,N'-carbonyldiimidazole |
| CH570391A5 (en) * | 1970-01-15 | 1975-12-15 | Air Prod & Chem | 1,3,4-Thiadiazole herbicides and fungicides - prepd. by reaction of carbamoyl chlorides with alkali metal derivs. of 2-amino-1,3,4-thiadiazoles |
| CH556862A (en) * | 1970-01-15 | 1974-12-13 | Air Prod & Chem | 1-(1,3,4-Thiadiazol-2-yl)-urea derivs as herbicides - and fungicides, prepd. from 2-amino-1,3,4-thiadiazoles |
| DE2028778A1 (en) * | 1970-06-06 | 1971-12-23 | Thiadiazolyl-urea herbicides - 5 - substd by sulphinyl or sulphonyl | |
| DE2044442C2 (en) * | 1970-09-03 | 1983-11-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,1,3-Trimethyl-3 - (- 5-Ethylsulfonyl-1,3,4-Thiadiazol-2-yl) -urea with herbicidal action |
| JPS5235672B2 (en) * | 1972-05-22 | 1977-09-10 | ||
| DE2246461C2 (en) * | 1972-09-21 | 1985-07-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,1,3-Trimethyl-3- (5-butylsulfonyl-1,3,4-thiadiazol-2-yl) urea and herbicidal agents containing this compound |
| FR2237894A1 (en) * | 1973-06-29 | 1975-02-14 | Velsicol Chemical Corp | Thidiazolyl ureidoacetaldehyde acetals - as herbicies |
| DE2341816A1 (en) * | 1973-08-16 | 1975-02-27 | Schering Ag | HERBICIDES 1,3,4-THIADIAZOL-2-YL URBAN MATERIAL |
| DE2350709A1 (en) * | 1973-10-05 | 1975-04-24 | Schering Ag | 1,3,4-THIADIAZOL-2-YL-UREA WITH SELECTIVE HERBICIDAL EFFECT |
| JPS583585B2 (en) * | 1977-06-10 | 1983-01-21 | 株式会社日立製作所 | Sample room for electron microscopes, etc. |
-
1976
- 1976-02-20 DE DE19762607481 patent/DE2607481A1/en not_active Withdrawn
-
1977
- 1977-01-07 RO RO7788970A patent/RO73052A/en unknown
- 1977-01-13 SU SU772439828A patent/SU648098A3/en active
- 1977-01-25 DK DK29577A patent/DK29577A/en unknown
- 1977-01-29 IN IN127/CAL/77A patent/IN155287B/en unknown
- 1977-02-01 CS CS77664A patent/CS193083B2/en unknown
- 1977-02-02 AR AR266423A patent/AR217638A1/en active
- 1977-02-02 AU AU21863/77A patent/AU2186377A/en not_active Expired
- 1977-02-03 BG BG7735323A patent/BG27713A3/en unknown
- 1977-02-10 LU LU76741A patent/LU76741A1/xx unknown
- 1977-02-10 CA CA271,481A patent/CA1077044A/en not_active Expired
- 1977-02-11 TR TR20545A patent/TR20545A/en unknown
- 1977-02-11 FI FI770452A patent/FI770452A/fi not_active Application Discontinuation
- 1977-02-14 BR BR7700890A patent/BR7700890A/en unknown
- 1977-02-16 IL IL51461A patent/IL51461A/en unknown
- 1977-02-17 SE SE7701776A patent/SE7701776L/en unknown
- 1977-02-18 NZ NZ183378A patent/NZ183378A/en unknown
- 1977-02-18 IE IE346/77A patent/IE44565B1/en unknown
- 1977-02-18 DD DD7700197438A patent/DD128655A5/en unknown
- 1977-02-18 ES ES456051A patent/ES456051A1/en not_active Expired
- 1977-02-18 NL NL7701752A patent/NL7701752A/en not_active Application Discontinuation
- 1977-02-18 BE BE175074A patent/BE851600A/en unknown
- 1977-02-18 ZA ZA770985A patent/ZA77985B/en unknown
- 1977-02-18 PT PT66210A patent/PT66210B/en unknown
- 1977-02-18 IT IT20428/77A patent/IT1118003B/en active
- 1977-02-18 SU SU772453508A patent/SU605520A3/en active
- 1977-02-18 GR GR52805A patent/GR62395B/en unknown
- 1977-02-18 PL PL1977196093A patent/PL101774B1/en unknown
- 1977-02-18 AT AT111377A patent/AT351314B/en not_active IP Right Cessation
- 1977-02-19 EG EG97/77A patent/EG12458A/en active
- 1977-02-21 GB GB7192/77A patent/GB1577523A/en not_active Expired
- 1977-02-21 FR FR7704886A patent/FR2341573A1/en not_active Withdrawn
- 1977-02-21 JP JP1802077A patent/JPS52102277A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| LU76741A1 (en) | 1977-06-30 |
| PT66210A (en) | 1977-03-01 |
| FI770452A (en) | 1977-08-21 |
| SU605520A3 (en) | 1978-04-30 |
| AU2186377A (en) | 1978-08-10 |
| BR7700890A (en) | 1977-10-18 |
| TR20545A (en) | 1981-10-15 |
| IL51461A (en) | 1980-03-31 |
| DE2607481A1 (en) | 1977-08-25 |
| AT351314B (en) | 1979-07-25 |
| SE7701776L (en) | 1977-08-21 |
| ATA111377A (en) | 1978-12-15 |
| RO73052A (en) | 1982-05-10 |
| IT1118003B (en) | 1986-02-24 |
| BG27713A3 (en) | 1979-12-12 |
| CA1077044A (en) | 1980-05-06 |
| CS193083B2 (en) | 1979-09-17 |
| IL51461A0 (en) | 1977-04-29 |
| JPS52102277A (en) | 1977-08-27 |
| ZA77985B (en) | 1977-12-28 |
| GB1577523A (en) | 1980-10-22 |
| AR217638A1 (en) | 1980-04-15 |
| BE851600A (en) | 1977-08-18 |
| SU648098A3 (en) | 1979-02-15 |
| NZ183378A (en) | 1979-01-11 |
| NL7701752A (en) | 1977-08-23 |
| DD128655A5 (en) | 1977-11-30 |
| DK29577A (en) | 1977-08-21 |
| FR2341573A1 (en) | 1977-09-16 |
| IE44565L (en) | 1977-08-20 |
| PT66210B (en) | 1978-07-12 |
| EG12458A (en) | 1979-03-31 |
| PL101774B1 (en) | 1979-01-31 |
| ES456051A1 (en) | 1978-02-16 |
| GR62395B (en) | 1979-04-10 |
| IN155287B (en) | 1985-01-12 |
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