GB2138684A - Fungicidal agents containing thiadiaxolyl-ureas - Google Patents
Fungicidal agents containing thiadiaxolyl-ureas Download PDFInfo
- Publication number
- GB2138684A GB2138684A GB08410103A GB8410103A GB2138684A GB 2138684 A GB2138684 A GB 2138684A GB 08410103 A GB08410103 A GB 08410103A GB 8410103 A GB8410103 A GB 8410103A GB 2138684 A GB2138684 A GB 2138684A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butyl
- formula
- cereal
- active compound
- thiadiazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- 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)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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)
Abstract
Fungicidal agents for use on cereal crops, comprise at least one substituted 5-t-buty(-1,3,4-thiadiazol-2-yl-urea of the formula <IMAGE> in which R represents t-butyl which is monosubstituted or polysubstituted by halogen, R<1> and R<2> independently of one another represent hydrogen or alkyl and R<3> represents alkyl or halogenoalkyl. The fungicide, optionally admixed with a diluent or carrier, is applied, in an amount sufficient to combat the fungus without killing the grain, immediately before sowing or during growth of the cereal. Alternatively, the fungicide may be applied to the cereal seed.
Description
SPECIFICATION
Fungicidal agents containing thiadiazolyl-ureas
The present invention relates to the use of known substituted 5-t-butyl-1 ,3,4-thiadiazol-2-yl-ureas as cereal fungicides.
The use of the substituted 5-t-butyl-1 ,3,4-thiadiazol-2-yl-ureas as herbicides is known (see DE-OS (German Published Specification) 2,423,469, DE-OS (German Published Specification) 2,614,842, DE-OS (German Published Specification) 3,113,328 and C.A. 88,84,572 [1978]), and in general a fungicidal action has also been mentioned.
Furthermore, it is known that organic sulphur compounds, such as, for example, zinc ethyiene-1,2- bis-(dithiocarbamate), possess fungicidal properties (see R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekâmpfungsmittel ' (Chemistry of Plant Protection Agents and Pest-combating agents),
Springer Verlag, Heidelberg, New York 1970, volume 2, page 65 et seq.).
However, the action of these compounds, particularly at low application rates and concentrations, is not always completely satisfactory in some fields of use.
It has been found that the known substituted 5-t-butyl-1 ,3,4-thiadiazol-2-yl-ureas of the general formula (I)
in which
R represents t-butyl which is monosubstituted or polysubstituted by halogen,
R1 and R2 independently of one another represent hydrogen or alkyl and
R3 represents alkyl or halogenoalkyl, have powerful fungicidal actions against fungi in cereals.
Surprisingly, the substituted 5-t-butyl-1 ,3,4-thiadiazol-2-yI-ureas of the general formula (I) have a more specific activity against fungal pathogens of cereal diseases than the thiocarbamates, such as, for example, zinc ethylene-l ,2-bis-(dithiocarbamate), which is known from the prior art and is a compound having the same direction of action.
The use, according to the invention, of the substituted 5-t-butyl-1 ,3,4-thiadiazol-2-yl-ureas thus represents an enrichment of the art.
Formula (I) gives a general definition of the substituted 5-t-butyl-1 ,3,4-thiadiazol-2-yl-ureas to be used according to the invention.
Preferred compounds of the formula (I) are those in which
R represents one of the radicals
wherein
X' represents halogen, in particular fluorine, chlorine or bromine and
X2 represents hydrogen or halogen, in particular fluorine, chlorine or bromine,
R1 and R2 independently of one another represent hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms and R3 represents straight-chain or branched alkyl having up to 4 carbon atoms or straight-chain or branched halogenoalkyl having up to 4 carbon atoms and up to 5 identical or different halogen atoms, in particular fluorine, chlorine or bromine.
Very particularly preferred compounds of the formula (I) are those in which
R represents one of the radicals
R' and R2 independently of one another represent hydrogen or methyl and R3 represents methyl, ethyl, n- and i-propyl, n-, i-, s- and t-butyl, fluoromethyl, chloromethyl, fluoroethyl, chloroethyl,
The following compounds of the general formula (I) may be mentioned as individual examples
Example No. R Rq R2 R3 CH3 1 F-CH2-C- CH3 H CH3 I CH3 CH3 2 Cl-CH2-C- CH3 H CH3 CH3 CH3 3 Cl-CH2-C- H H CH3 I CH3 CH3 4 F-CH2-C- CH3 H n-C3H7 CH3 CH3 5 F-CH2-C- CH3 H i-C4Hg CH3 CH3 6 F-CH2-C- H CH3 CH3 I CH3 CH3 7 Cl2CH-C- CH3 H CH3 CH3
Example No. R R' R2 R3 CH2F 8 CH3-C- CH3 H CH3 I CH2F CH2Cl, 9 CH3-C- CH3 H CH3 CH2CI CH3 10 F-CH2-C- CH3 H n-C4Hg CH3 CH3 11 CI-CH2-C- H H -CH2-CH2-CI CH3 CH3 12 Cl-CH2-C- H CH3 CH3 I CH3 CH3 13 F-CH2-C- H H CH3 CH3 CH2F 14 CH3-C- H H CH3 CH2F The substituted 5-t-butyl-1,3,4-thiadiazol-2-yl-ureas of the formula (I) which are to be used
according to the invention are known.They are obtained, for example, if either the corresponding 2 amino-1 ,3,4-thiadiazole derivatives of the formula (II)
in which R and R' have the meaning given above, are reacted with isocyanates of the formula (III)
O=C=N--R2 or O=C=N--R3 (III) in which R2 and R3 have the meaning given above, or the amines of the formula (IV)
in which R2 and R3 have the meaning given above, are reacted with dimeric isocyanates of the formula (V)
in which
R has the meaning give above, or with carbamoyl halides of the formula (VI)
in which
R and R' have the meaning given above and
Hal represents fluorine, chlorine or bromine, if appropriate in the presence of a diluent, such as, for example, ethyl acetate, and, if appropriate, in the presence of an acid-binding agent, such as, for example, triethylamine, and, if appropriate, in the presence of a catalyst, such as, for example, dibutyltin laurate, at temperatures between 200C and 1 200C (see DE-OS (German Published Specification) 2,423,469, DE-OS (German Published Specification) 2,614,842, DE-OS (German Published Specification), 3,113,328 and C.A. 88, 84,572r (1978)).
The active compounds according to the invention exhibit a powerful fungicidal action against fungal pathogens of cereal diseases, and can be employed in practice for combating undesired fungi
The active compounds are suitable for use as plant protection agents, especially as cereal fungicides, maize and rice being included.
Thus, fungicidal agents can be employed in plant protection for combating
Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
The good toleration, by plants, of the active compounds, at the concentrations required for combating plant diseases, permits treatment of above-ground parts of plants, of vegetative propagation stock and seeds, and of the soil.
The active compounds according to the invention can be employed with good success for combating cereal diseases, such as, for example, the brown rust of wheat causative organism (Puccinia recondita), and against the cereal diseases causative organism Pyrenophora teres and Cochliobolus sativus, against powdery mildew of cereals causative organisms and against the rice disease causative organism Pellicularia sasakii.
The active compounds can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnared with active compound, very fine capsules in polymeric substances and in coating compositions for seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans, fumigating coils and the like, as well as ULV cold mist and warm mist formulations.
These formulations are produced in known manner, for example by mixing the active compounds with extenders, that is, liquid solvents liquefied gases under pressure, and/or solid carriers, optionally
with the use of surface-active agents, that is, emulsifying agents and/or dispersing agents, and/or foamforming agents. In the case of the use of water as an extender, organic solvents can, for example, also
be used as auxiliary solvents.As liquid solvents, there are suitable in the main: aromatics, such as
xylene, toluene or alkyl naphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such
as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane
or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers
and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,
strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, as well as water; by
liquefied gaseous extenders or carriers are meant liquids which are gaseous at normal temperature and
under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as
butane, propane, nitrogen and carbon dioxide; as solid carriers there are suitable: for example ground
natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or
diatomaceous earth, and ground synthetic minerals, such as highly disperse silicic acid, alumina and
silicates; as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well as albumin hydrolysation products; as dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
The active compounds according to the invention can be present in the formulations or in the various use forms as a mixture with other known active compounds, such as fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, bird repellents, growth factors; plant nutrients and agents for improving soil structure.
The active compounds can be used as such or in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They are used in the customary manner, for example by watering, immersion, spraying, atomising, misting, vaporising, injecting, forming a slurry, brushing on, dusting, scattering, dry dressing, moist dressing, wet dressing, slurry dressing or encrusting.
In the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a substantial range. They are, in general, between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
In the treatment of seed, amounts of active compound of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
For the treatment of soil, active compound concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.2% by weight, required at the place of action.
Use examples:
The compound indicated here is used as a comparative substance in the use example bellow:
zinc ethylene- 1 ,2-bis-(dithiocarbamate).
EXAMPLE A
Puccinia test (wheat)/protective
Solvent: 100 parts by weight of dimethylformamide
Emulsifier: 0.25 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
To test for protective activity, young plants are inoculated with a spore suspension of Puccinia recondita in a 0.1% strength aqueous agar solution. After the spore suspension has dried on, the plants are sprayed with the preparation of active compound until dew-moist. The plants remain in an incubation cabin at 200C and 100% relative atmospheric humidity for 24 hours.
The plants are placed in a greenhouse at a temperature of about 200C and a relative atmospheric humidity of about 80% in order to promote the development of rust pustules Evaluation is carried out 1 0 days after the inoculation.
In this test, a clearly superior activity compared with the prior art is shpwn, for example, by the compounds according to the following preparation examples:
TABLE A
Puccinia Test (wheat)/protective
Active compound Disease infestation concentration in in % of the untreated the spray liquor control.
Active compound in % by weight S Ii CH > -NH-C-SX (A) 0,025 100 S t tnoo CH3 -r NCH CL-cH2-C11 s1N(3 (2) 0,025 0,0 tH3 CO-NH-CH3 CH3 r\N H (3) 0,025 125 Ct-CH2-C S t N I \CO-NH-CH3 CH3 13 N.-,N ,CH3. (1) 0,025 lit,5 II S N I \C0-NH-CH CH3 f-CH -C < S t N (4) 0w025 41,3 C113 'c0-NH-C3H7 -n CH3 rllric /CH3 CH3 F-CH2-c1 N 1 3 (5) 0,025 S0,0 cx3 XC0-NH-CH2-CIH c1{3 Cl CH C M S g N/CH3 (7) 0 or5 0,0 CH3 'CO-nM-CR3 CH3 NUN I II,H CH S - R F-CH2-C1SN CO-N (6) 0,025 25,o CH3 \CH3 PREPARATION EXAMPLES:
EXAMPLE 1::
6.3 g (0.11 mole) of methyl isocyanate are added dropwise to a solution of 18.9 g (0.1 mole) of 2 (1 ,1 -dimethyl-2-fluoroethyl)-5-methylamino- 1 ,3,4-thiadiazole and a few drops of dibutyl-tin laurate in 100 ml of ethyl acetate. The reaction mixture is then heated under reflux for 3 hours. After cooling, the reaction solution is washed with 1 M citric acid, saturated sodium bicarbonate solution and water, dried over sodium sulphate and evaporated down. The residue is recrystallised from ethyl acetate/petroleum ether (1:1).
15.7 g (63.8% of theory) of 1-[5-(1,1 -dimethyl-2-fluoroethyl)-1 ,3,4-thiadiazol-2-yl]-1 3-dimethyl- urea of melting point 161 0C to 1 620C are obtained.
Preparation of the starting material:
80.3 g (0.525 mole) of phosphorus oxychloride are added to a mixture of 51.5 g (0.5 mole) of 4 methyl-thiosemicarbazide, 64.6 g (0.5 mole) of 92.8% strength 2,2-dimethyl-3-fluoropropionic acid and 425 my of dioxane in the course of 35 minutes, under reflux. The reaction mixture is heated under reflux for 4 hours, until the evolution of hydrogen chloride is complete. After the mixture has cooled, the solution is decanted, and the residue is dissolved, in 1 ,250 ml of water while heating on a water bath.
The solution is adjusted to pH 11 with 50 g of sodium hydroxide, and is extracted with chloroform. The extract is washed with water and then evaporated down. 69.4 g (73.4% of theory) of 2-( 1,1 -dimethyl-2- fluoroethyl)-5-methylamino-1 ,3,4-thiadiazole of melting point 78-800C are obtained.
816 g (5.1 moles) of bromine are added dropwise at OOC to a solution of 680 g (17 moles) of sodium hydroxide in 2,260 ml of water, followed by the addition of 200 g (1.7 moles) of 3,3-dimethyl4-fluorobutan-2-one at OOC to 50C, and the mixture is stirred for 2 hours at 200C. Thereafter, it is filtered, the bromoform phase is separated off and the aqueous phase is decolorised with a 2 M sodium disulphite solution. After acidification with 850 ml of concentrated hydrochloric acid, the aqueous phase is extracted with methylene chloride. The organic phase is dried over sodium sulphate and then evaporated down. 153.6 g (69.9% of theory) of 2,2-dimethyl-3-fluoro-propionic acid of melting point 71 0C are obtained.
Claims (17)
1. Fungicidal agents for combating cereal diseases, characterised in that they contain at least one substituted 5-t-butyl-l ,3,4-thiadiazol-2-yl-urea of the formula (I)
in which
R represents t-butyl which is monosubstituted or polysubstituted by halogen,
R1 and R2 independently of one another represent hydrogen or alkyl and R3 represents alkyl or halogenoalkyl.
2. Fungicidal agents for combating cereal diseases, characterised in that they contain at least one substituted 5-t-butyl-1 ,3,4-thiadiazol-2-yl-urea of the formula (I) according to Claim 1, in which
R represents one of the radicals
wherein
X1 represents halogen and
X2 represents hydrogen or halogen, P1 and R2 independently of one another represent hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms and R3 represents straight-chain or branched alkyl having up to 4 carbon atoms or straight-chain or branched halogenoalkyl having up to 4 carbon atoms and up to 5 identical or different halogen atoms.
3. Fungicidal agents for combating cereal diseases, characterised in that they contain at least one substituted 5-t-butyl-1 ,3,4-thiadiazol-2-yl-urea of the formula (I) according to Claim 1, in which
R represents one of the radicals
wherein
X' represents fluorine, chlorine or bromine and
X2 represents hydrogen or fluorine, chlorine or bromine,
R1 and R2 independently of one another represent hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms and R3 represents straight-chain or branched alkyl having up to 4 carbon atoms or straight-chain or branched halogenoalkyl having up to 4 carbon atoms and up to 5 identical or different fluorine, chlorine or bromine atoms.
4. Fungicidal agents for combating cereal diseases,-characterised in that they contain at least one substituted 5-t-butyl-l ,3,4-thiadiazol-2-yl-urea of the formula (I) according to Claim 1, in which R1 and R2 independently of one another represent hydrogen or methyl and R3 represents methyl, ethyl, n- and i-propyl, n-, i-, s- and t-butyl, fluoromethyl, chloromethyl, fluoroethyl, chloroethyl,
and R represents one of the radicals
5. Use of substituted 5-t-butyl-1 ,3,4-thiadiazol-2-yl-ureas of the formula (I) according to Claim 1 for combating fungal pathogens of cereal diseases.
6. Process for combating fungal pathogens of cereal diseases, characterised in that substituted 5-t-butyl 1 3,4-thiadiazol-2-yl-ureas of the formula (I) according to Claim 1 are allowed to act on fungi and/or their habitat.
7. Process for the preparation of fungicidal agents for combating cereal diseases, characterised in that substituted 5-t-butyl-l ,3,4-thiadiazol-2-yl-ureas of the formula (I) according to Claim 1 are mixed with extenders and/or surface-active agents.
8. A method of combating fungi in cereal crops in which there is applied to the fungi or a habitat thereof associated with cereal growth, an active compound which is a compound of formula (I) as defined in claim 1, alone or in the form of a composition containing said active compound in admixture with a diluent or carrier.
9. A method according to claim 8 in which said habitat is cereal seed or a cereal crop growing area.
1 0. A method according to claim 8 or 9, characterised in that a composition is used containing from 0.1 to 95% of the active compound, by weight.
11. A method according to claim 10, characterised in that a composition is used containing from 0.5 to 90% of the active compound by weight.
1 2. A method according to claim 9, characterised in that the active compound is applied to soil in an amount of 0.00001 to 0.1 percent by weight.
13. A method according to claim 12, characterised in that the active compound is applied to soil in an amount of 0.0001 to 0.2 percent by weight.
14. A method according to claim 9, characterised in that the active compound is applied to seed in an amount of 0.001 to 50 g per kg of seed.
1 5. A method according to claim 14, characterised in that the active compound is applied to seed in an amount of 0.01 to 10 g per kg of seed.
1 6. A method according to any of claims 8 to 15, characterised in that the active compound is any one of the compounds as identified in Example 1 to 14.
17. Cereal crops, characterised by being protected from fungi, by being grown in areas in which immediately prior to and/or during the time of the growing a compound of formula (I) as defined in claim 1 was applied, alone or in an admixture with a diluent or carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833314190 DE3314190A1 (en) | 1983-04-19 | 1983-04-19 | FUNGICIDAL AGENT |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8410103D0 GB8410103D0 (en) | 1984-05-31 |
| GB2138684A true GB2138684A (en) | 1984-10-31 |
Family
ID=6196802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08410103A Withdrawn GB2138684A (en) | 1983-04-19 | 1984-04-18 | Fungicidal agents containing thiadiaxolyl-ureas |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS59205304A (en) |
| AU (1) | AU2680884A (en) |
| BE (1) | BE899439A (en) |
| BR (1) | BR8401819A (en) |
| DE (1) | DE3314190A1 (en) |
| DK (1) | DK203184A (en) |
| FR (1) | FR2544587A1 (en) |
| GB (1) | GB2138684A (en) |
| IT (1) | IT1209529B (en) |
| NL (1) | NL8401161A (en) |
| SE (1) | SE8401989L (en) |
| ZA (1) | ZA842914B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276552A (en) * | 2011-06-15 | 2011-12-14 | 中国农业大学 | 1,3,4-thiadiazoline derivative containing cyclopropanyl, preparation method thereof and application thereof as bactericide |
-
1983
- 1983-04-19 DE DE19833314190 patent/DE3314190A1/en not_active Withdrawn
-
1984
- 1984-04-10 SE SE8401989A patent/SE8401989L/en not_active Application Discontinuation
- 1984-04-11 NL NL8401161A patent/NL8401161A/en not_active Application Discontinuation
- 1984-04-13 AU AU26808/84A patent/AU2680884A/en not_active Abandoned
- 1984-04-17 JP JP59075900A patent/JPS59205304A/en active Pending
- 1984-04-17 BE BE0/212778A patent/BE899439A/en not_active IP Right Cessation
- 1984-04-18 BR BR8401819A patent/BR8401819A/en unknown
- 1984-04-18 GB GB08410103A patent/GB2138684A/en not_active Withdrawn
- 1984-04-18 DK DK203184A patent/DK203184A/en not_active Application Discontinuation
- 1984-04-18 IT IT8420605A patent/IT1209529B/en active
- 1984-04-18 ZA ZA842914A patent/ZA842914B/en unknown
- 1984-04-18 FR FR8406110A patent/FR2544587A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102276552A (en) * | 2011-06-15 | 2011-12-14 | 中国农业大学 | 1,3,4-thiadiazoline derivative containing cyclopropanyl, preparation method thereof and application thereof as bactericide |
| CN102276552B (en) * | 2011-06-15 | 2013-07-10 | 中国农业大学 | 1,3,4-thiadiazoline derivative containing cyclopropanyl, preparation method thereof and application thereof as bactericide |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2544587A1 (en) | 1984-10-26 |
| DK203184A (en) | 1984-10-20 |
| BR8401819A (en) | 1984-11-27 |
| GB8410103D0 (en) | 1984-05-31 |
| DE3314190A1 (en) | 1984-10-25 |
| ZA842914B (en) | 1984-12-24 |
| IT8420605A0 (en) | 1984-04-18 |
| AU2680884A (en) | 1984-10-25 |
| SE8401989D0 (en) | 1984-04-10 |
| BE899439A (en) | 1984-10-17 |
| SE8401989L (en) | 1984-10-20 |
| JPS59205304A (en) | 1984-11-20 |
| IT1209529B (en) | 1989-08-30 |
| NL8401161A (en) | 1984-11-16 |
| DK203184D0 (en) | 1984-04-18 |
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