GB2066814A - Herbicidal 2,5- dialkylphenylurea derivatives - Google Patents
Herbicidal 2,5- dialkylphenylurea derivatives Download PDFInfo
- Publication number
- GB2066814A GB2066814A GB8038889A GB8038889A GB2066814A GB 2066814 A GB2066814 A GB 2066814A GB 8038889 A GB8038889 A GB 8038889A GB 8038889 A GB8038889 A GB 8038889A GB 2066814 A GB2066814 A GB 2066814A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- carbon atoms
- composition
- methyl
- general formula
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- 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<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Novel compounds of the general formula <IMAGE> wherein R1 = C1-2 alkyl, R2 = C2-4 alkyl, C3-4 cycloalkyl or methylcyclopropyl, are useful as herbicides.
Description
SPECIFICATION 2,5-dialkyiphenylursa derivatives, process for their preparation, herbicidal compositions containing them, and method of combating weeds using them
This invention relates to certain 2,5-dialkylphenylurea derivatives, a process for their preparation, herbicidal compositions containing them, and a method of combating weeds using them.
U.S. Patent Specification No. 2,655,447 discloses an extremely wide class of urea derivatives having herbicidal properties. In the period of over twenty-five years since these compounds were prepared, considerable research has been directed towards the use of ureas as herbicides and a number of herbicidal ureas have been commercialised.While some of these commercially available urea herbicides have found good acceptance in certain crop use areas -- e.g., 3-(4-isopropylphenyl)-1,1 -di- methylurea or "Isoproturon" in cereal crops and 3-(3-trifluoromethylphenyl) l,l-dimethylurea or "Cotomn" in cotton -- there is still a continuing need for new compounds which exhibit advantageous spectrums of activity against weed species coupled with high crop tolerances.
It has now been found that certain 3-(2,5-dialkylphenyl)-1,1-dimethylureas not specifically disclosed in the aforementioned U.S. Specification No. 2,655,447 have especially attractive herbicidal properties.
The invention therefore provides a compound of the general formula I
in which R, is an alkyl group of one or two carbon atoms and R2 represent a branched chain or straight chain alkyl group of from two to four carbon atoms, a cycloalkyl group of three to four carbon atoms, or a methylcyclopropyl group. These novel 2,5-dialkylphenyl-ureas exhibit high herbicidal activity for various? weed species while being exceptionally tolerant to cotton.
Preferably, R1 in formula I above is methyl and R2 is a branched chain alkyl group of 3 or 4 carbon atoms, for example isopropyl or tertiarybutyl, or a cyclopropyl group. In this regard, the most preferred compound is 3-(-2-methyl-5-isopropylphenyl)- 1,1 -dimethyl urea.
The invention also provides a process for the preparation of a compound of formula I, which comprises reacting an aniline of the general formula II or a hydrohalide salt thereof:
wherein Ra and R2 are as defined above with either (a) a dimethylcarbamoyl halide, preferably chloride; or (b) phosgene (COCI2), to produce an isocyanate of the general formula
and reacting at least part of the isocyanate with dimethylamine.
Process (a) may be carried out with or without a solvent. Suitable solvents include hydrocarbons and halogenated hydrocarbons, for example benzene, toluene or carbon tetrachloride. Preferably it is carried out under substantially anhydrous conditions. Since the reaction is a condensation reaction involving the elimination of hydrogen halide it is preferably carried out in the presence of a hydrohalgenating agent; organic or inorganic bases are suitable; sodium acetate has been found to be especially useful when working without a solvent, and organic bases such as triethylamine or pyridine are suitable when using a solvent. The reaction is preferably carried out at a temperature in the range of from 0 to 800 C, conveniently at room temperature, and the reaction mixture may be worked up by conventional means.
Process (b) is suitably carried out in the presence of a solvent, for example a hydrocarbon, e.g.
toluene, at a temperature in the range of from 80 to 1200 C; conveniently, the reaction may be carried out at the reflux temperature of the solvent used. If desired, the resulting isocyanate of formula Ill may be isolated from the reaction mixture, but preferably it is reacted in situ with dimethylamine. This reaction is suitably carried out at a temperature in the range of from 0 to 300C, conveniently at room temperature. The desired product may be isolated by any suitable method.
The invention further provides a herbicidal composition which comprises a compound of the formula I together with a suitable carrier. The invention also provides a method of combating undesired plant growth at a locus, which comprises applying to the locus a compound or a composition according to the invention.
A carrier in a composition according to the invention is any material with which the active ingredient is formulated to facilitate application to the locus to be treated, which may for example be a plant seed or soil, or to facilitate storage, transport or handling. A carrier may be a solid or a liquid, including a material which is normally gaseous but which has been compressed for form a liquid, and any of the carriers normally used in formulating herbicidal compositions may be used.
Suitable solid carriers include natural and synthetic clays and silicates, for example natural silicas such as diatomaceous earths; magnesium silicates, for example talcs; magnesium aluminium silicates, for example attapulgites and vermiculites; aluminium silicates, for example kaolinites, montmorillonites and micas; calcium carbonate; calcium sulphate; synthetic hydrated silicon oxides and synthetic calcium or aluminium silicates; elements, for example carbon and sulphur; natural and synthetic resins, for example coumarone resins,.polyvinyl chloride, and styrene polymers and copolymers; solid polychlorophenols; bitumen; waxes, for example beeswax, paraffin wax, and chlorinated mineral waxes, and solid fertilisaers, for example superphosphates.
Suitable liquid carriers include water; alcohols, for example isopropanol and glycols; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers; aromatic or araliphatic hydrocarbons, for example benzene, toluene and xylene; petroleum fractions, for example kerosine and light mineral oils; chlorinated hydrocarbons, for example carbon tetrachloride, perchloroethylene and trichloroethane. Mixtures of different liquids are often suitable.
Agricultural compositions are often formulated and transported in a concentrated form which is subsequently diluted by the user before application. The presence of small amouns of a carrier which is a surface-active agent facilitates this process of dilution. Thus preferably at least one carrier in a composition according to the invention is a surface-active agent. For example the composition may contain at least two carriers, at least one of which is a surface-active agent.
A surface-active agent may be an emulsifying agent, a dispersing agent or a wetting agent; it may nonionic or ionic. Examples of suitable surface-active agents include the sodium ar calcium salts of polyacrylic acids and lignin sulphonic acids; the condensation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol; condensates pf these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohol or alkyl phenols, for example p-octylphenol orp-octylcresol, with ethylene oxide and/or propylene oxide; sulphates or sulphonates of these condensation products; alkali or alkaline earth metal salts, preferably sodium salts, of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulphate, sodium secondary alkyl sulphates, sodium salts or sulphonated castor oil, and sodium alkylaryl sulphonates such as sodium dodecylbenzene sulphonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.
The compositions of the invention may for example be formulated as wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols. Wettable powders usually contain 25, 50 and 75% w of active ingredient and usually contain, in addition to solid inert carrier, 310% w of a dispersing agent and, where necessary, 0-10% w of stabiliser(s) and/or other additives such as penetrants or stickers. Duts are usually formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant, and are diluted in the field with further solid carrier to give a composition usually containing 21 10% w of active ingredient.
Granules are usually prepared to have a size between 10 and 100 BS mesh (1.676--0.!52 mm), and may be manufactured by agglomeration or impregnation techniques. Generally, granules will contain 2125% w active ingredient and 0--1 09/0 w of additives such as stabilisers, slow release modifiers and binding agents. Emulsifiable concentrates usually contain, in addition to a solvent and, when necessary, co-solvent, 1050% w/v active ingredient, 2-20% w/v emulsifiers and 0-20% w/v of other additives such as stabilisers, penetrants and corrosion inhibitors. Suspension concentrates are usually compounded so as to obtain a stable, non-sedimenting flowable product and usually contain 10-75% w active ingredient 0.515% w of dispersing agents, 0.1-10% w of suspending agents such as protective colloids and thixotropic agents, 0-10% w of other additives such as defoamers, corrosion inhibitors, stabilisers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble; certain organic solids or inorganic salts may be present dissolved in the formulation to assist in preventing sedimentation or as anti-freeze agents for water.
Aqueous dispersions and emulsions, for example compositions obtained by diluting a wettable powder or a concentrate according to the invention with water, also lie within the scope of the present invention. The said emulsions may be of the water-in-oil or the oil-in-water type, and may have a thick 'mayonnaise'-like consistency.
The compositions of the invention may also contain other ingredients, for example, other compounds possessing insecticidal or fungicidal properties.
The following Examples illustrate the invention.
EXAMPLE 1
Preparation of 3-(2-methyl-5-isopropylphenyl) 1,1 -dimethyluree 2-methyl-5-isopropylaniline (4.5 g) and anhydrous sodium acetate (2.4 g) were stirred together as a solid mixture, and dimethylcarbamoyl chloride (5.4 g) was added over 15 minutes. The mixture was allowed to stand at room temperature overnight, and then treated with water followed by extraction with methylene chloride. After drying over magnesium sulphate, the solvent was evaporated, and the resultant solid was recrystallised from hexane. 1.5 g of the desired product, melting at 72-730C, were obtained.
Analysis C H N Calculated for C13H20N20 70.9 9.1 12.7
Found 71.0 9.3 12.5
EXAMPLE 2
Alternative Preparation of the compound of Example 1
COCI2 gas was passed through a refluxing solution of 2-methyl-5-isopropylaniline (8 g) in, toluene (1 50 ml) for T hour. Dry nitrogen gas was passed through the solution to remove excess COCI2, and dimethylamine (8 g, anhydrous) dissolved in toluene (50 ml) was then added at room temperature.
The solution was then evaporated down, and the residue treated with hexane to give 9.5'g of the desired compound as a white precipitate, melting point 720C.
EXAMPLE 3
Preparation of 3-(2-methyl-5-tertiarybutylphenyl)- 1,1 -dimethylurea 2-methyl-4-tertl -butylaniline (7 g) in toluene (10 ml) solution was added dropwise to a solution of
COCI2 in toluene (100 ml). The resulting reaction mixture was heated to reflux for w hour and dry nitrogen gas was passed through the solution to remove excess COCI2. After cooling, anhydrous dimethylamine (3 g) dissolved in toluene (10 ml) was then added and a precipitate formed. The precipitate was filtered and recrystallised from hexane to afford 6.5 g of the desired product melting at 116-1170C.
Analysis C H
Calculated for C14H22N20 71.1 9.3
Fond 71.2 9.6
EXAMPLE 4
Herbicidal Activity
To evaluate their herbicidal activity, compounds according to the invention (Examples 1 and 3) and a compound not according to the invention, 3-(2,5-dimethylphenyl)-1,1-dimethylurea, were tested using as a representative range of plants: maize,Zea mays(MZ); rice, Oryza sativa ( R); barnyard grass,
Echinochloa crusgalli (BG); oat, Avena sativa (0); linseed, Linum usitatissimum (L); mustard, Sinapsis alba (M); sugar beet, Beta vulgaris (SB) and soya bean, Glycine max (S).
The tests fall into two categories, pre-emergence and post-emergence. The pre-emergence tests involved spraying a liquid formulation of the compount onto the soil in which the seeds of the plant species mentioned above had recently been sown. The post-emergence tests involved two types of test, viz., soil drench and foliar spray tests. In the soil drench tests the soil in which the seedling plants of the above species were growing, was drenched with a liquid formulation containing the compound of the invention, and in the foliar spray tests the seedling plants were sprayed with such a formulation.
The soil used in the tests was a prepared horticultural loam.
The formulations used in the tests were prepared by diluting with water, a solution of the test compound in acetone containing 0.4% by weight of an alkylphenol/ethylene oxide condensate available under the trade name TRITON X-155. The acetone solutions were diluted with water and the resulting formulations applied at dosage levels corresponding with water and the resulting formulations applied at dosage levels corresponding to 5 kg and 1 kg of active material per hectare in a volume equivalent to 650 litres per hectare in the soil spray and foliar spray tests, and at a dosage level equivalent to 10 kilograms of active material per hectare in a volume equivalent to approximately 3,000 litres per hectare in the soil drench tests.
In the pre-emergence tests untreated sown soil and in the post-emergence tests untreated soil bearing seedlings plants were used as controls.
The herbicidal effects of the test compounds were assessed visually eleven days after spraying the foliage and drenching the soil and twelve days after spraying the soil, and were recorded on a 0--9 scale. A rating 0 indicates growth as untreated control, a rating 9 indicates death. An increase of 1 unit on the linear scale approximately to a 10% increase in the level of effect.
The results of the tests are set out in Table I below.
TABLE 1
Soil Drench 10 kg/ha Follar Spray Pre-emergence Compound Tested Dosage (Source or Chemical name) Mz R BG O L M SB S Mz R BG O L M SB S Mz R BG O L M SB S Example 1 7 6 8 8 7 9 9 9 5 5 3 5 4 7 9 9 8 7 7 9 8 7 9 9 8 1 2 0 2 2 4 6 7 6 4 4 7 4 4 8 8 7 Example 3 7 7 7 6 7 9 9 7 5 5 3 7 6 8 9 8 7 7 5 8 8 4 9 9 6 1 0 0 0 1 4 9 7 6 4 1 6 0 0 7 9 2 3-(2,5-dimethylphenyl)-1,1- 2 2 0 1 4 7 6 5 0 0 4 2 7 9 8 6 0 0 3 0 0 6 7 1 dimethylurea 0 0 0 0 2 6 6 5 0 0 0 0 0 0 1 0 EXAMPLE 5
Selective Herbicidal Activity
The pre-emergence herbicidal activity of 3-(2-methyl-5-isopropylpphenyl)-1 ,1 -dimethylurea was
evaluated against various crop and weed species in the following manner.Seeds of the various plants to
be tested were planted in containers and the test compound was applied to the soil at two different fixed dosages of 1.1 and 2.2 kilogram per hectare. The planted soil was held under controlled
conditions of temperature, moisture and light for 9 to 10 days. The amounts of germination and growth
were evaluated on a O to 9 scale, with the numeric ratings, in this case, having the following meanings:
Rating Meaning
9 No living tissue
8 Living tissue, but plant expected to die
7 Plant badly damaged, but expected to live
6 Plant badly damaged, but expected to recover completely
5 Unacceptable damage for crop plants, insufficient damage to weeds 34 Definite damage
1-2 Plant slightly affected, possibly by the chemical, possibly
due to biological variability
O No visible effect
The plant species tested were as follows: corn,zea maize (dekalb X363); cotton, Gossypium hirsutum; Rice, Oryza sativa (Calrose); grain sorghum, Sorghum vulgare (Pioneer 265); soybean, Glycine max (Amsoy 71); wheat, Triticum aestivum (Cajeme 71); barnyard grass, (watergrass), Echinochloa crus-galli; crabgrass, Digitaria sanguinalis; downy brome, Bromus tectorum; giant foxtail, Setoria faberi; johnsongrass, Sorghum halepense; wild oats,Avena fatua; yellow foxtail, setaria lutescens; cocklebur,
Xanthium pensylvanicum; hemp sesbania, (coffeeweed), Sesbania exaltata; jimson weed, Datura stramonium; lambsquarters, Chenopodium album; morningglory, Ipomea puprpurea; mustard, Sinopis alba; pigweed, Amoranthus retroflexus; prickly sida, Sida spinosa; sicklepod, Cassia obtusifolia; velvetleaf, Abutllon theophrasti.
The results of the test are reported in Table II below.
TABLE II
Phytotoxicity Rating at Indicated Dosage
Plant Species 1.1 kg/ha 2.2 kg/ha
Corn 3 9
Cotton O 0
Rice 6 8
Grain Sorghum 5 9
Soybean 8 9
Sugarbeet 9 9
Wheat 4 6
Barnyardgrass 9 9
Crabgrass 9 9
Downy Brome 3 8
TABLE II (continued)
Phytotoxicity Rating at Indicated Dosage
Plant Species 1.1 kg/ha 2.2 kg/ha
Giant Foxtail 6 9
Johnsongrass 9 9
Wild Oats 4 7
Yellow Foxtail 9 9
Cocklebur 7 8
Coffeeweed 6 9
Jimson weed 9 9
Lambsquarters 9 9
Morning glory 9 9
Mustard 9 9
Pigweed 9 9
Prickly Sida 9 6
Sicklepod 6 9
Velvetleaf 9 9
As can be seen from Table II above, the compound according to the invention, 3-(2-methyl-5 isopropylphenyl) 1 ,1 -dimethylurea is essentially nontoxic to cotton while giving good control of various weed species.
Claims (14)
1. A compound of the general formula:
in which RX is an alkyl group of one or two carbon atoms and R2 represents a branched chain or straight chain alkyl group of from two to four carbon atoms or a cycloalkyl group of from three to four carbon atoms or a methylcyclopropyl group.
2. A compound as claimed in Claim 1, in which R is methyl.
3. A compound as claimed in either Claim 1 or Claim 2, in which R2 is a branched chain alkyl group of three or four carbon atoms or cycloDropyl.
4. 3-(2-methyl-5-isopropyl-phenyl)- 1,1 -dimethylurea.
5. A. process for the preparation of a compound as claimed in either of Claim 1 or Claim 2, which comprises reacting an aniline of the general formula li or a hydrohalide salt thereof:
in which R, and R2 are as defined in Claim 1 or claim 2 with either: (a) a dimethylcarbamoyl halide; or (b) phosgene, to produce an isocyanate of the general formula
and reacting at least part of the isocyanate with dimethylamine.
6. A process as claimed in Claim 5, in which process (a) is carried out in the presence of a dehydrohalogenating agent.
7. A process as claimed in Claim 5, in which process (a) is carried out using dimethylcarbamoyl chloride.
8. A process as claimed in Claim 5, carried out substantially as described in any one of Examples 1 to 3 herein.
9. A compound as claimed in Claim 1, whenever prepared by a process as claimed in any one of
Claims 5 to 8.
10. A herbicidal composition which comprises a compound as claimed in any one of Claims 1 to 4 and 9, together with a suitable carrier.
11. A composition as claimed in Claim 10, which comprises at least two carriers, at least one of which is a surface-active agent.
12. A method of combating undesired plant growth at a locus, which comprises applying to the locus a compoundf as claimed in any one of Claims 1 to 4 and 9 or a composition as claimed in either of
Claims 10 and 11.
13. The use of a compound as claimed in any one of Claims 1 to 4 and 9 as a herbicide.
14. A method of combating undesired weed growth in cotton which comprises applying to the locus where cotton is grown a compound as claimed in any one of Claims 1 to 4 and 9 or a composition as claimed in either of Claims 10 and 11.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7942224 | 1979-12-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2066814A true GB2066814A (en) | 1981-07-15 |
| GB2066814B GB2066814B (en) | 1983-11-09 |
Family
ID=10509686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8038889A Expired GB2066814B (en) | 1979-12-06 | 1980-12-04 | Herbicidal 2,5-dialkylphenylurea derivatives |
Country Status (30)
| Country | Link |
|---|---|
| JP (2) | JPS5692259A (en) |
| AT (1) | AT381006B (en) |
| AU (2) | AU540420B2 (en) |
| BE (2) | BE886365A (en) |
| BG (1) | BG33431A3 (en) |
| BR (2) | BR8007953A (en) |
| CA (1) | CA1201725A (en) |
| CH (2) | CH645347A5 (en) |
| CU (1) | CU35374A (en) |
| DD (2) | DD154955A5 (en) |
| DE (2) | DE3045770A1 (en) |
| DK (2) | DK519580A (en) |
| EG (1) | EG14536A (en) |
| ES (2) | ES497435A0 (en) |
| FR (2) | FR2471370A1 (en) |
| GB (1) | GB2066814B (en) |
| HU (1) | HU185226B (en) |
| IL (2) | IL61628A0 (en) |
| IT (2) | IT1141111B (en) |
| KE (1) | KE3410A (en) |
| NL (2) | NL8006569A (en) |
| NZ (1) | NZ195760A (en) |
| OA (1) | OA06709A (en) |
| PH (1) | PH16412A (en) |
| PL (3) | PL127924B1 (en) |
| PT (1) | PT72156B (en) |
| SE (2) | SE8008535L (en) |
| TR (1) | TR20936A (en) |
| YU (2) | YU307680A (en) |
| ZA (2) | ZA807581B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2577221B1 (en) * | 1985-02-11 | 1987-02-20 | Rhone Poulenc Agrochimie | PROCESS FOR THE PREPARATION OF A SUBSTITUTED PHENYLUREA |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2655447A (en) * | 1952-02-14 | 1953-10-13 | Du Pont | Composition and method |
| GB1164160A (en) * | 1966-12-30 | 1969-09-17 | Shell Int Research | N,N-Disubstituted Amino Acid Derivatives and their use as Herbicides |
| IL31574A0 (en) * | 1968-02-13 | 1969-04-30 | Ciba Ltd | Use of certain ureas for combating weeds |
| US3649241A (en) * | 1969-07-22 | 1972-03-14 | Du Pont | 1-(p-cumyl)-3,3-dimethylureas as selective herbicide |
-
1980
- 1980-11-04 CA CA000363944A patent/CA1201725A/en not_active Expired
- 1980-11-25 CU CU8035374A patent/CU35374A/en unknown
- 1980-11-27 BE BE1/10053A patent/BE886365A/en not_active IP Right Cessation
- 1980-11-27 BE BE1/10052A patent/BE886364A/en not_active IP Right Cessation
- 1980-12-03 NL NL8006569A patent/NL8006569A/en not_active Application Discontinuation
- 1980-12-03 NL NL8006568A patent/NL8006568A/en not_active Application Discontinuation
- 1980-12-03 EG EG749/80A patent/EG14536A/en active
- 1980-12-04 AU AU65058/80A patent/AU540420B2/en not_active Ceased
- 1980-12-04 YU YU03076/80A patent/YU307680A/en unknown
- 1980-12-04 IL IL61628A patent/IL61628A0/en unknown
- 1980-12-04 SE SE8008535A patent/SE8008535L/en not_active Application Discontinuation
- 1980-12-04 PL PL1980232826A patent/PL127924B1/en unknown
- 1980-12-04 IT IT26437/80A patent/IT1141111B/en active
- 1980-12-04 BR BR8007953A patent/BR8007953A/en not_active IP Right Cessation
- 1980-12-04 SE SE8008536A patent/SE8008536L/en not_active Application Discontinuation
- 1980-12-04 FR FR8025793A patent/FR2471370A1/en active Granted
- 1980-12-04 CH CH895980A patent/CH645347A5/en not_active IP Right Cessation
- 1980-12-04 HU HU802901A patent/HU185226B/en not_active IP Right Cessation
- 1980-12-04 NZ NZ195760A patent/NZ195760A/en unknown
- 1980-12-04 ES ES497435A patent/ES497435A0/en active Granted
- 1980-12-04 AT AT0592780A patent/AT381006B/en not_active IP Right Cessation
- 1980-12-04 OA OA57267A patent/OA06709A/en unknown
- 1980-12-04 FR FR8025795A patent/FR2471371A1/en active Granted
- 1980-12-04 TR TR20936A patent/TR20936A/en unknown
- 1980-12-04 ZA ZA00807581A patent/ZA807581B/en unknown
- 1980-12-04 AU AU65059/80A patent/AU6505980A/en not_active Abandoned
- 1980-12-04 BR BR8007954A patent/BR8007954A/en unknown
- 1980-12-04 PL PL1980228264A patent/PL125931B1/en unknown
- 1980-12-04 YU YU03081/80A patent/YU308180A/en unknown
- 1980-12-04 ES ES497434A patent/ES8200652A1/en not_active Expired
- 1980-12-04 DK DK519580A patent/DK519580A/en not_active Application Discontinuation
- 1980-12-04 DE DE19803045770 patent/DE3045770A1/en active Granted
- 1980-12-04 DE DE19803045785 patent/DE3045785A1/en not_active Withdrawn
- 1980-12-04 ZA ZA00807582A patent/ZA807582B/en unknown
- 1980-12-04 PT PT72156A patent/PT72156B/en unknown
- 1980-12-04 GB GB8038889A patent/GB2066814B/en not_active Expired
- 1980-12-04 JP JP17032380A patent/JPS5692259A/en active Pending
- 1980-12-04 IL IL61629A patent/IL61629A0/en unknown
- 1980-12-04 DD DD80225710A patent/DD154955A5/en unknown
- 1980-12-04 DK DK519480A patent/DK154502C/en not_active IP Right Cessation
- 1980-12-04 IT IT8026436A patent/IT8026436A0/en unknown
- 1980-12-04 BG BG8049871A patent/BG33431A3/en unknown
- 1980-12-04 DD DD80225709A patent/DD154956A5/en unknown
- 1980-12-04 JP JP17032280A patent/JPS5692258A/en active Granted
- 1980-12-04 CH CH895880A patent/CH645346A5/en not_active IP Right Cessation
- 1980-12-04 PL PL1980228263A patent/PL125992B1/en unknown
- 1980-12-05 PH PH24957A patent/PH16412A/en unknown
-
1984
- 1984-05-31 KE KE3410A patent/KE3410A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4609394A (en) | Phenyl benzothiadiazole ether herbicides | |
| US5262388A (en) | Herbicidal compounds | |
| US4299778A (en) | N'Cyclopropyl-N-(fluorophenyl)-N-hydroxyureas | |
| GB2066814A (en) | Herbicidal 2,5- dialkylphenylurea derivatives | |
| EP0002842B1 (en) | Propanthioic acid derivatives, herbicidal and/or plant growth regulating compositions comprising these derivatives and method of destroying or preventing undesirable plant growth | |
| EP0149269B1 (en) | Heterocyclic herbicides | |
| EP0174685A2 (en) | Ether herbicides | |
| US5073192A (en) | Diphenyl ether herbicides | |
| EP0280367B1 (en) | Glycine compounds | |
| US4994616A (en) | Anilide herbicides | |
| AU606890B2 (en) | Diphenyl ether herbicides | |
| EP0286153B1 (en) | Herbicidal vinylamine derivatives | |
| US4494981A (en) | Use of certain pyrimido[5,4-e]-1,2,4-triazines for controlling the growth of unwanted plants | |
| EP0184256B1 (en) | Diphenyl ether herbicides | |
| US4345076A (en) | Certain herbicidal N-(para-(6-chloro-3-pyridazinyloxy)phenyl)trifluoromethanesulfonamides | |
| US4313755A (en) | N-Cyclopyopyl-N-(fluorophenyl)-N-acylureas and their herbidical use | |
| EP0123327B1 (en) | Chloroacetanilides, their preparation, their use, compositions containing them, and method of combating undesired plant growth | |
| EP0149268A2 (en) | Herbicidal composition and method of combating plant growth | |
| US4474598A (en) | Oxazolyl-substituted thiadiazolidinediones | |
| GB2155462A (en) | Heterotricyclic herbicides/fungicides | |
| EP0015605B1 (en) | Novel urea derivative, a process for its preparation, herbicidal composition containing it, a method of combating undesired plant growth using it | |
| EP0124155B1 (en) | Pyrazine compounds, their preparation and their use, compositions containing them and method of combating undesired plant growth | |
| EP0136754A1 (en) | Thiadiazole herbicides | |
| GB2035309A (en) | Diphenyl esters and herbicidal compositions containing them | |
| US4334916A (en) | Use of N-cyclopropyl-N'-(2-Fluorophenyl)urea as a selective herbicide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |