GB2058748A - Salts of herbicidal 1,2,4- thiadiazolyl-5-urea derivatives - Google Patents
Salts of herbicidal 1,2,4- thiadiazolyl-5-urea derivatives Download PDFInfo
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- GB2058748A GB2058748A GB8017190A GB8017190A GB2058748A GB 2058748 A GB2058748 A GB 2058748A GB 8017190 A GB8017190 A GB 8017190A GB 8017190 A GB8017190 A GB 8017190A GB 2058748 A GB2058748 A GB 2058748A
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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
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
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- 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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- Pest Control & Pesticides (AREA)
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- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
The salts according to the invention correspond to the formula I <IMAGE> wherein 1 DIVIDED n M<n)<+) is the ion equivalent of an an inorganic or organic base, R is C1C8-alkyl which is optionally interrupted once or several times by oxygen, sulfur or nitrogen, or is unsubstituted or substituted by halogen or cyano or by phenyl which in its turn can be substituted, or it is C3-C8-alkenyl which is unsubstituted or substituted by halogen, or it is C3-C8-alkynyl or C3-C8-cycloalkyl, or phenyl which is unsubstituted or substituted, R1 is C1-C4-alkyl or C1-C4- alkoxy, R2 is C1-C4-alkyl, and X is the direct bond, sulfur, oxygen or a sulfinyl or sulfonyl group. By virtue of their greater solubility in water, these salts are better suited for application as herbicides and as active substances regulating plant growth. They are also able to antagonise the phytotoxic action of some known herbicides on cultivated plants, without reducing the herbicidal action of the mixture.
Description
SPECIFICATION
Salts of herbicidal 1,2,4-thiadiazolyl-5-urea derivatives and the use thereof
The invention relates to novel salts of known herbicidally active 1 ,2,4-thiadiazolyl-5-urea derivatives, to processes for producing them, to compositions containing them as active substance, and to the use thereof for the selective control of weeds in crops of cultivated plants and for the reduction of plant growth.
Herbicidally effective 1 ,2,4-thiadiazolyl-5-urea derivatives are known, for example from the
German Offenlegungsschriften (Published Specifications) Nos. 1,670,924, 2,037,474 and 2,113,033, and from the Belgian Patent Specification No. 679,1 38.
It has now been shown that the salts of the present invention increase to a considerable extent the action of 1 ,2,4-thiadiazolyl-5-urea derivatives. The salts exhibit moreover a level of selectivity higher than that of the ureas. These salts can be used for controlling weeds in crops of useful plants, especially in crops of cereals.
Furthermore, it has been found that surprisingly the salts according to the invention, when applied in mixed combinations with certain herbicides from the classes comprising phenylureas, triazines, thiocarbamates and other herbicides, not only have the expected additive effect of the individual components but also the effect of cancelling out the harmful action of the herbicides on cereal cros, such as wheat and barley, that is to say, of antagonising, in the manner of a "safener", the original phytotoxicity of the herbicide. Mixtures of this type suffer no loss of activity against wild grasses and dicotyledonous weeds. They thus act cumulatively to form a broadly effective herbicide and at the same time to cancel out or neutralise the phytotoxicity of the respective herbicide on wheat and on other varieties of cereals.This combined action offers the possibility of using mixtures of this kind as broad-band herbicides in the post-emergence process of combating the most serious mono- and dicotyledonous weeds in crops of wheat and of other varieties of cereals.
The salts according to the invention of the 1 ,2,4-thiadiazolyl-5-urea derivatives correspond to the formula I
wherein 1 - Mna+ is the cation equivalent of a base, n
M is an n-valent alkali metal or alkaline-earth metal cation, or an ammonium radical
n as an integer 1 or 2 corresponds to the valency of the cation, and Ra, Rb, Rc and Rd independently
of one another are each hydrogen or benzyl, or a C1-C4-alkyl group which is unsubstituted or
substituted by -OH, -CN or C1-C4-alkoxy, R is C1-C8-alkyl which is optionally interrupted once or several times by oxygen, sulfur or nitrogen,
or which is unsubstituted or substituted by halogen or cyano, or by phenyl which in its turn can be
substituted up to three times by halogen, cyano, nitro, trifluoromethyl, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylthio, or it is C3-C8-alkenyl which is unsubstituted or substituted by halogen,
or it is C3-C8-alkynyl, C3-C8-cycloalkyl, or
phenyl which is unsubstituted or substituted up to three times by halogen, cyano, nitro,
trifluoromethyl, C1-C4-alkyl, C1-C4-a lkoxy or C1-C4-alkylthio, R, is C1-C4-alkyl or C1-C4-alkoxy, R2 is C1-C4-alkyl, and
X is the direct bond, sulfur, oxygen or a sulfinyl or sulfonyl group.
By alkyl in these definitions are meant branched-chain and straight-chain alkyl groups having up to the given number of carbon atoms. Preferred alkyl groups R are methyl and branched-chain radicals, such as isopropyl or sec- and tertiary butyl; and the preferred alkyl groups R, and R2 are methyl and ethyl. The alkoxy group Rz which is preferred is methoxy.
The salts according to the invention of 1 ,2,4-thiadiazolyl-5-urea derivatives can occur in various tautomeric forms which most probably correspond to the following formula:
Such salts have not been described hitherto. They are produced according to the invention by reacting a 1 ,2,4-thiadiazolyl-5-urea derivative of the formula Il
in the presence of a solubility-promoting agent, with an essentially equimolar amount of a base of the formula Ill
MOH (III) In the above formulae, MR, R, R, and X have the meanings given under the formula I.
The reaction of the reactants is performed at a temperature of between OOC and the boiling point of the reaction mixture, generally however at 00--400C, that is, at room temperature. The duration of the reaction is between 1/2 and about 2 hours.
Depending on the employed base, the solubility-promoting agents used can be organic polar solvents, on their own or diluted with water. Suitable solvents and dispersing agents are low alkanols, acid nitriles such as acetonitrile, ethers such as dimethyl or diethyl ether, tetrahydrofuran or dioxane, also toluene, acid amides such as dimethyl-formamide, ketones such as acetone, and so forth. The salts formed in the said manner are isolated from the reaction mixture by concentrating the solvent mixture by evaporation, by removal by distillation under normal or reduced pressure or by precipitation in less polar solvents or solvent mixtures.
The following Examples are intended to further illustrate the production according to the invention of the salts of the formula I. Parts and percentage values are by weight, and temperatures are given in degrees Centigrade.
EXAMPLE 1
24 g of N-[3-trifluoromethyl-1 ,2,4-thiadiazolyl-(5)j-N',N'-dimethylurea are dissolved in 200 ml of methanol, and the solution is cooled to about 5 . There are then added with stirring 4 g of solid pulverised sodium hydroxide; stirring is continued for half an hour, and the solvent is subsequently distilled off in vacuo. The sodium salt remaining behind is dissolved in a small amount of warm methanol, and then precipitated with diisopropyl ether whilst stirring is maintained. The yield is 23.6 g of the sodium salt of N-[3-trifluoromethyl-1 ,2,4-thiadiazolyl-(5)]-N',N'-dimethylurea, which decomposes at above 2700.
EXAMPLE 2
4.3 ml of isopropylamine are added dropwise, with stirring, to a solution of 12.8 g of N-[3 trifluoromethyl-1 ,2,4-thiadiazolyl-( 5)]-N'-methyl-N'-methoxyurea in 75 ml of diisopropyl ether. The isopropylamine salt, firstly precipitating as oil, becomes crystalline after a short time. After a subsequent stirring for half an hour, the product is filtered off with suction, washed with diisopropyl ether and dried.
The yield is 14.3 g of isopropylammonium salt of N-[3-trifluoromethyl-1 ,2,4-thiadiazolyl-(5)]-N'-methyl- N'-methoxyurea, which melts at 1 520 with decomposition.
The following further salts of the formula I are produced in a manner analogous to that of producing the above compounds.
1N" Physical constants No. RX NR,R, 1 n (m.p.) 1 CF3 N(CH3)2 Na > 270" (decomp.) 2 CF3 N(CH,)OCH, NH3C3H7iso 152" (decomp.) 3 CF3 N(CH3)OCH3 Na > 270 (decomp.) 4 Cl2CH N(CH3)2 Na 189--91" (decomp.) 5 CINCH N(CH3)OCH3 Na 169" (decomp.) 6 CH3S N(CH3)0CH3 Na > 265 7CH2 S N(CHa)OCH3 Na 256" (decomp.) 8 CCI, N(CHa)2 NH(CH3) 9 Cl2CH N(CH3)OCH3 NH3C3H7iso 133 (decomp.) 10 Cl2CF N(CH3)OCH3 Na 1900 (decomp.) 11 CICF2 N(CH3)OCH3 Na 249 (decomp.) 12 (CH3)3C- N(CHa)2 Na 13 (CH3)3C- N(CH3)0CH3 Na > 240 14 (OH3)3O N(CH3)QCH3 NH3C3H7iso 15 (CH3)2CH- N(CH3 )2 Na 16 (CH3)2cH N(CH3)OCH3 Na 248 (decomp.) 17 (CH;;)2CH N(CH3)0CH3 NH2(C2H40H) 18 CH3 N(CH3)2 Na 19 CH3 N(CH3)OCH3 NH3C3H,iso 20 CH3 N(CH3)OCH3 Na 216 (decomp.) 21 O N(CH3)2 Na 22 O N(CH3)2 HN(CH3)3 23 \ = / N(CH3)OCH3 Na 199 (decomp.) 24 CItC N(CH3)2 Na 25 Cl;C N(CH3)0CHa Na 177 (decomp.) 26 Cl3C N(CH3)2 NH(CH3)3
n Mn Physical constants No. RX NRtR2 1 (m.p.) 27 9 Cm2 0 N(CH3)0CH3 Na 256" (decomp.) 28 CICH2O N(OH3)OCH3 Na 29 CH3SC2 N(CH3)2 Na 30 CH3S02 N(OH3)OCH3 NH3C3H7iso 31 CH3SO N(CH3)2 Na 32 CH3S N(OH3)OCH3 Na 1214-123 33 C(CH3)3S N(CH3)2 Na 34 C(CH3)3S N(CH3)OCH3 NH3C3H7iso 35 CCI3 N(CH3)OCH3 NH(CH3)3 109' (decomp.) 36 CCí3 N(CH3)0CH3 NH3QHaOH 117-120 37 isoCsH1, N(CH3)2 Na 38 OaH,? N(CH3)2 Na 39 isoC5Hll N(OH3)OCH3 Na 40 9 gQ-CH2S N(CH3)2 Na 41 OH3O N(CH3)2 Na 42 9 Cm20 N(CH3)2 Na 43 5 CH2NH- N(CH317 Na 44 9 S02- N(CH3)2 Na 45-CH2so2 N(CH3)2 Na 46 0013 N(CH3)0CH3 NHlOlH7iso 124-129
The salts of the formula I of the present invention have negligible toxicity for warm-blooded animals, and application of the salts presents no problems. They are stable compounds which are soluble in water and in customary organic solvents, such as alcohols, ketones, dimethylformamide and dimethylsulfoxide. The applied amounts required are usually between 0.1 and 5 kg per hectare.
The salts of the formula I have herbicidal activity in the case of both pre- and post-emergence application, and in crops of mono- and dicotyledonous plants the salts can be used as herbicidal agents, on their own or together with other herbicides, the phytotoxic action of which against useful plants they are in some cases able to antagonise.
The salts of the formula I can be used on their own or together with herbicides which are optionally to be antagonised, as well as together with suitable carriers and/or other additives. Suitable carriers and additives may be solid or liquid and correspond to the substances common in formulation practice, such as natural or regenerated mineral substances, solvents, dispersing agents, wetting agents, adhesives, thickeners, binders or fertilisers.
The content of active substance in commercial preparations is between 0.01 and 90%.
For application, the salts of the formula I can be in the following forms (the weight-percentage figures in brackets signify advantageous amounts of active substance): solidpreparations: dusts and scattering agents (up to 10%); granuiates [coated, impregnated or
homogeneous granules] and pellets (1 to 80%); liquid preparations: a) water-dispersible concentrates of active substance: wettable powders and pastes (25 to 90% in the
commercial packing, 0.01 to 15% in ready-for-use solutions); emulsion
concentrates and solution concentrates (10 to 50%; 0.01 to 15% in ready-for-use
solutions); b) solutions (0.1 to 20%), for example for dressings or aerosols.
The salts of the formula I of the present invention can be formulated for example as follows:
Dust: The following substances are used to produce a) a 5% dust and b) a 2% dust: a) 5 parts of salt or of active-substance mixture, and
95 parts of talcum; b) 2 parts of salt or of active-substance mixture,
1 part of highly dispersed silidid acid, and
97 parts of talcum.
The active substances are mixed and ground with the carriers, and can be applied in this form by dusting on.
Granulate: The following substances are used to produce a 5% granulate:
5 parts of salt or of active-substance mixture,
0.25 part of epichlorohydrin,
0.25 part of cetyl polyglycol ether,
3.50 parts of polyethylene glycol, and
91 parts of kaolin (particle size 0.3-0.8 mm).
The active substance is mixed with epichlorohyrin and dissolved in 6 parts of acetone, and the polyethylene glycol and cetyl polyglycol ether are then added. The solution thus obtained is sprayed onto kaolin, and the acetone is subsequently evaporated off in vacuo. A microgranulate of this type can be advantageously worked into seed furrows.
Wettable powder: The following constituents are used to produce a) a 70% wettable powder, b) a 40% wettable powder, c) and d) a 25% wettable powder, and e) a 10% wettable powder: a) 70 parts of salt or of active-substance mixture,
5 parts of sodium dibutyl-naphthalene sulfonate,
3 parts of a naphthalenesulfonic acid/phenolsulfonic acid/formaldehyde condensate (3:2:1),
10 parts of kaolin, and
12 parts of Champagne chalk; b) 40 parts of salt or of active-substance mixture,
5 parts of sodium lignin sulfonate,
1 part of sodium dibutyl-naphthalene sulfonate, and
54 parts of silicic acid; c) 25 parts of salt or of active-substance mixture,
4.5 parts of calcium lignin sulfonate, 1.9 parts of Champagne chalk/hydroxyethyl cellulose mixture (1:1),
1.5 parts of sodium dibutyl-naphthalenesulfonate,
19.5 parts of silicic acid,
19.5 parts of Champagne chalk, and
28.1 parts of kaolin;
d) 25 parts of salt or of active-substance mixture,
2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol,
1.7 parts of Champagne chalk/hydroxyethyl cellulose mixture (1:1), 8.3 parts of sodium aluminium silicate, 1 6.5 parts of kieselguhr, and
46 parts of kaolin; and
e) 10 parts of salt or of active-substance mixture,
3 parts of a mixture of the sodium salts of saturated fatty alcohol sulfates,
5 parts of a naphthalenesulfonic acid/formaldehyde condensate, and
82 parts of kaolin.
The active substances are intimately mixed in suitable mixers with the additives, and the mixture is
then ground in appropriate mills or rollers to obtain wettable powders which have excellent wetting and
suspension properties, and which can be diluted with water to give suspensions of the concentration
desired.
Emulsifiable concentrate: The following substances are used to produce a 25% emulsifiable
concentrate:
25 parts of salt or of an active-substance mixture,
2.5 parts of epoxidised vegetable oil,
10 parts of an alkylarylsulfonate/fatty alcohol polyglycol ether mixture,
5 parts of dimethylformamide, and
57.5 parts of xylene.
Emulsions of the required concentration can be prepared from such concentrates by dilution with water.
The novel salts of the formula I possess excellent herbicidal properties, and are suitable for controlling gramineous weeds and particularly broad-leaved weeds in the widest variety of cultivated crops. Also annual and perennial species of weeds that are deep rooted and difficult to control are checked in growth or destroyed by these active substances. The novel salts of the formula I can thus be used at low concentrations for the selective control of weeds, for example for the control of wild chamomile varieties (Matricaria spp.) goose grass (Galium aparine), parsnip (Pastinaca sativa), fox-tail grass varieties, for example Amaranthus spp., wild mustard varieties (Sinapis spp.) grasses such as
Echinochloa spp. or lolium spp., and millet varieties (Panicum spp.) in cereal, maize and cotton crops and in root crops and forage crops.The salts of the formula I can be applied both before germination (pre-emergence) and after germination (post-emergence) of the plants. At high concentrations, that is to say, upwards of about 3 kg of active substance per hectare, the novel active substances can be used for the complete destruction and prevention of undesired plant growth. In small applied amounts, some salts of the formula I exhibit a growth-inhibiting action.
The testing of the herbicidal action (pre- and post-emergence) of the salts of the formula I is performed by the following test methods:
Pre-emergence herbicidal action (inhibition of germination)
Immediately after sowing of the test plants in seed trays in a greenhouse, the surface of the soil is treated with an aqueous dispersion of the active substance, obtained from a 25% emulsion concentrate by dilution with water. Four different concentration series are used, corresponding to 4, 2, 1 and 0.5 kg of active substance per hectare. The seed trays are left in the greenhouse at 22--250C with 5070% relative humidity, and the test is evaluated after 3 weeks.
The following for example are used as test plants:
Hordeum (barley) Setaria italica
Triticum (wheat) Echinochloa crus galli Zea (maize) Beta vulgaris
Sorghum hybr. (millet) Sida spinosa
Oryza (rice) Sesbania exaltata
Glycine (soya bean) Amaranthus retroflexus
Gossypium (cotton) Sinapis alba
Avena fatua Ipomoea purpurea
Lolium perenne Galium aparine
Alopecurus myosuroides Pastinaca sativa
Bromus tectorum Rumex sp.
Cyperus esculentus Chrysanthemum leucum.
Rottboellia exaltata Abutilon sp.
Digitaria sanguinalis Solanum nigrum.
Post-emergence herbicidal action (contact herbicide)
A largish number (at least 7) of weeds and of cultivated plants, both monocotyledonous and dicotyledonous, are sprayed after emergence (in the 4- to 6-leaf stage) with an aqueous activesubstance dispersion in dosage amounts of 0.06, 0.125, 0.25 and 0.5 kg of active substance per hectare, and they are then kept at 24--260C with 4560% relative humidity. The test is evaluated at least 1 5 days after treatment.
The tested salts of the formula I exhibited both in the pre-emergence process and post-emergence process a marked activity against in particular dicotyledonous plants and weeds, whereas cereals such as wheat, rice and maize remain unharmed. A good herbicidal action was obtained with salt No. 25.
The salts of the formula I surprisingly also have the property of being able to protect cultivated plants from being attacked by agricultural chemicals harmful to plants, particularly by herbicides of the most varied classes of substances, including 1,3,5-triazines, 1,2,4-triazinones, phenylurea derivatives, carbamates, thiolcarbamates, halogenoacetanilides, halogenophenoxyacetic acid esters, and so forth, in cases where these are not tolerant or not sufficiently tolerant to cultivated plants.
As an antidote, a salt of the formula I, depending on the purpose of application, can be used for pretreatment of the seed of the cultivated plant (dressing of the seed or of the cuttings), or can be introduced into the soil before or after sowing, or alternatively can be applied, on its own or together with the herbicide, before or after emergence of the plants. The treatment of the plant or of the seed with the antidote can therefore be effected essentially independently of the point of time of application of the phytotoxic chemicals. It can however also be carried out simultaneously (tank mixture). The preemergence treatment includes both the treatment of the cultivated area before sowing and the treatment of the sown cultivated area before emergence of the plants.
The applied amounts of antidote in proportion to the herbicide are largely governed by the type of application. When a field treatment is performed, the amounts of antidote salt of the formula I to phytotoxic chemical are in the ratio of 1:100 to 5:1, preferably 1 :20 to 1:1. In the case of seed dressing and similar specific protective measures, however, much smaller amounts of antidote salt are required in comparison with for example the amounts of herbicide used later per hectare of cultivated land (for example about 1:3000 to 1:1000). There is as a rule only a loose relationship between protective measures such as seed dressing with an antidote salt of the formula I and possible subsequent field -treatments with agricultural chemicals.Pretreated seed and plant material can safely come into contact later with various chemicals in agriculture, horticulture and forestry without suffering damage.
The antagonistic action protecting cultivated plants against strong herbicides was tested using the following tests:
Antidote action in the case of separate application (antidote pre-e-mergence, herbicide post-emergence)
General procedure: Small flower pots (upper diameter 6 cm) are filled with sandy loam, in which the cultivated plant is sown. After the seeds have been covered, the substance to be tested as an antidote is sprayed in dilute solution onto the surface, the applied amount when converted being equivalent to 4 kg of active substance per hectare. The pots are then held at 2023 C with 6070% relative humidity.
When the plants after 10 days have reached the 2-to 3-leaf stage, they are treated with the appropriate amount of herbicide. An evaluation is made fourteen days after application of the herbicide. Plants without antidote protection serve as control specimens.
Pre-emergence antidote test (basic test)
General procedure: Small flower pots (upper diameter 6 cm) are filled with garden soil, into which the cultivated plant is sown, covered over and lightly pressed down. The substance to be tested as antidote is then sprayed on as a dilute solution in an amount which is equivalent to 4 kg of active substance per hectare. The herbicide is sprayed on immediately afterwards in a corresponding manner. After 1 8 days standing at about 20--230C with 6070% relative humidity, an evaluation is made.
Plants without antidote protection are used as control plants.
In this test, the salt No. 2 according to the invention was able to protect cultivated millet against the phytotoxic action of an overdose of the herbicide N-(1 '-methyl-2'-methoxy-ethyl)-N-chloroacetyl-2ethyl-6-methyl-aniline.
Antidote test with seed soaking
Rice seeds of the IR 8 variety are saturated during 48 hours with solutions of the test substances of 10, 100 or 1000 ppm. The seeds are subsequently allowed to dry until they no longer stick together.
Rectangular plastic pots (8 x 8 cm, 10 cm in height) are filled to within 2 cm of the upper edge with sandy loam. In each pot are sown 4 g of seed, and the seed is only very slightly covered (about the diameter of a seeds. The soil is maintained in a moist (not boggy condition. A herbicide is then applied in dilute solution and in an amount which, when converted, is equivalent to 1.5 kg of active substance per hectare. When the plants have germinated and have grown to a height of about 5 cm, they are transplanted into a seed tray, the soil in which is covered with 2 cm of standing water. 7 and 18 days, respectively after transplanting, the condition of the plant is assessed.
The compounds Nows. 1,2 and 5 were able in this test to protect the rice seedlings against the phytotoxic action of the employed chloroacetanilide herbicide.
Claims (9)
1. A novel salt of 1 ,2,4-thiadiazolyl-5-urea derivative of the formula I
wherein 1 -- MR O is the cation equivalent of a base, n
M is an n-valent alkali metal or alkaline-earth metal cation, or an ammonium radical
n as an integer 1 or 2 corresponds to the valency of the cation, and Ra, Rb, Rc and Rd independently
of one another are each hydrogen or benzyl or C1-C4-alkyl group which is unsubstituted or
substituted by -OH, -ON or C1-C4-alkoxy, R is C1-C8-alkyl which is optionally interrupted once or several times by oxygen, sulfur or nitrogen,
or which is unsubstituted or substituted by halogen, or cyano, or by phenyl which in its turn can be
substituted up to three times by halogen, cyano, nitro, trifluoromethyl, C1-C4-alkyl, C1-C4-alkoxy orC1-C4-alkylthio, or it is C3-C8-alkenyl which is unsubstituted or substituted by halogen,
or it is C3-C8-alkynyl, C3-C8-cycloalkyl, or phenyl which is unsubstituted or substituted up to three times by halogen,
cyano, nitro, trifluoromethyl, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylthio, R, is C1-C4-alkyl or C1-C4-alkoxy, R2 is C1-C4-alkyl, and
X is the direct bond, sulfur, oxygen or a sulfinyl or sulfonyl group.
2. The sodium salt of N-l3-trifluoromethyl-1 ,2,4-thiadiazolyl-(5)j-N',N'-dimethyl urea.
3. The sodium salt of N-[3-trifluoromethyl-1,2,4-thiadiazolyl-(5)]-N'-methyl-N'-methoxyurea.
4. The sodium salt of N-[3-trichloromethyl-1,2,4-thiadiazolyl-(5)-N'-methyl-N'-methoxyurea.
5. The production of a salt of a 1 ,2,4-thiadiazolyl-5-urea derivative of the formula I, Claim 1,
which comprises reacting a 1 ,2,4-thiadiazolyl-5-urea derivative of the formula II
wherein R, Rr, R2 and X have the meanings given under the formula 1, in the presence of a solubilitypromoting agent, with an essentially. equimolar amount of a base of the formula III
MOH (III), wherein M has the meaning given under the formula I, and isolating in a known manner the formed salt from the reaction mixture.
6. A herbicidal composition which contains as active substance at least one salt of the formula I,
as defined in Claim 1.
7. A process for selectively controlling weeds in crops of cultivated plants, which process
comprises applying to the fields planted with the useful plants an effective amount of a salt of the
formula I, as defined in Claim 1, on its own or together with a herbicide.
8. The use of a salt of the formula I, as defined in Claim 1, or of a composition containing it, as a
selective herbicide in crops of cereals, maize, rice, cotton, soya bean and sugar beet.
9. A salt of the formula I, as defined in Claim 1, substantially as hereinbefore described with
reference to any one of the foregoing Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH484179 | 1979-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2058748A true GB2058748A (en) | 1981-04-15 |
Family
ID=4283488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8017190A Withdrawn GB2058748A (en) | 1979-05-23 | 1980-05-23 | Salts of herbicidal 1,2,4- thiadiazolyl-5-urea derivatives |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS55160771A (en) |
| AU (1) | AU5865980A (en) |
| BE (1) | BE883399A (en) |
| DE (1) | DE3019259A1 (en) |
| ES (1) | ES491731A0 (en) |
| FR (1) | FR2457289A1 (en) |
| GB (1) | GB2058748A (en) |
| IL (1) | IL60133A0 (en) |
| IT (1) | IT8022264A0 (en) |
| NL (1) | NL8002944A (en) |
| ZA (1) | ZA803050B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0394043A1 (en) * | 1989-04-19 | 1990-10-24 | Sumitomo Chemical Company, Limited | An amide compound and its production and use |
| US5264448A (en) * | 1989-04-19 | 1993-11-23 | Sumitomo Chemical Company, Limited | Amide compound and its production and use |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA01933A (en) * | 1965-04-06 | 1970-02-04 | Pechiney Saint Gobain | Thiazole derivatives. |
| DE1670924B2 (en) * | 1967-09-19 | 1976-11-18 | Bayer Ag, 5090 Leverkusen | 1,2,4-THIADIAZOLYL UREA DERIVATIVES |
| US3673203A (en) * | 1969-10-22 | 1972-06-27 | Exxon Research Engineering Co | 1,2,4-thiadiazolyl ureas |
| CH549338A (en) * | 1970-03-19 | 1974-05-31 | Agripat Sa | HERBICIDAL AGENT. |
| DE2407634A1 (en) * | 1974-02-18 | 1975-08-28 | Bayer Ag | ANGULAR CLAMP ON 3-TERT-BUTYL-1, 2,4-THIADIAZOLYL- (5) ANGULAR CLAMP FOR -URA, PROCESS FOR THEIR PRODUCTION AND THEIR USE AS SELECTIVE HERBICIDES |
| DE2745968A1 (en) * | 1977-10-10 | 1979-04-19 | Schering Ag | Defoliant compsn. esp. for cotton - contains synergistic mixt. of thiadiazolyl-urea and di:phenyl-urea, or thio analogues |
-
1980
- 1980-05-20 DE DE19803019259 patent/DE3019259A1/en not_active Withdrawn
- 1980-05-20 IL IL60133A patent/IL60133A0/en unknown
- 1980-05-21 BE BE0/200690A patent/BE883399A/en unknown
- 1980-05-21 FR FR8011314A patent/FR2457289A1/en not_active Withdrawn
- 1980-05-21 NL NL8002944A patent/NL8002944A/en not_active Application Discontinuation
- 1980-05-22 AU AU58659/80A patent/AU5865980A/en not_active Abandoned
- 1980-05-22 ES ES491731A patent/ES491731A0/en active Granted
- 1980-05-22 IT IT8022264A patent/IT8022264A0/en unknown
- 1980-05-22 ZA ZA00803050A patent/ZA803050B/en unknown
- 1980-05-23 GB GB8017190A patent/GB2058748A/en not_active Withdrawn
- 1980-05-23 JP JP6881980A patent/JPS55160771A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0394043A1 (en) * | 1989-04-19 | 1990-10-24 | Sumitomo Chemical Company, Limited | An amide compound and its production and use |
| US5264448A (en) * | 1989-04-19 | 1993-11-23 | Sumitomo Chemical Company, Limited | Amide compound and its production and use |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA803050B (en) | 1981-06-24 |
| DE3019259A1 (en) | 1980-12-04 |
| ES8104263A1 (en) | 1981-04-16 |
| BE883399A (en) | 1980-11-21 |
| FR2457289A1 (en) | 1980-12-19 |
| NL8002944A (en) | 1980-11-25 |
| IT8022264A0 (en) | 1980-05-22 |
| AU5865980A (en) | 1980-11-27 |
| IL60133A0 (en) | 1980-07-31 |
| ES491731A0 (en) | 1981-04-16 |
| JPS55160771A (en) | 1980-12-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |