GB2121034A - Herbicidal urea derivatives of isoxazole - Google Patents
Herbicidal urea derivatives of isoxazole Download PDFInfo
- Publication number
- GB2121034A GB2121034A GB08310916A GB8310916A GB2121034A GB 2121034 A GB2121034 A GB 2121034A GB 08310916 A GB08310916 A GB 08310916A GB 8310916 A GB8310916 A GB 8310916A GB 2121034 A GB2121034 A GB 2121034A
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- Prior art keywords
- compound
- urea
- methyl
- butylisoxazol
- weeds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Novel herbicidal urea compounds of the formula: <IMAGE> wherein R is lower alkyl; n is 0 or 1; and m is 0 or an integer from 1 to 6 are disclosed.R
Description
SPECIFICATION
Urea compounds, their preparation and use
This invention relates to new chemical compositions of matter and more specifically to new urea compounds of the formulas:
wherein R is lower alkyl,
n is O or 1 and
m is O or an integer from 1 to 6.
The preferred compounds have the structural formula:
The compounds of the present invention are particularly useful as herbicides.
The term "lower" as used herein designates a straight or branched carbon chain of up to six carbon atoms.
The compounds of the present invention can be prepared by reacting a compound of the formula:
with two molar amounts of an amine of the formula:
This reaction can be effected by heating a mixture of the isocyanate dimer and the amine in an inert reaction medium such as toluene with warming and stirring until the reactants dissolve.
After this occurs, the product can be recovered by standard procedures for the removal of the solvent and can be further purified by standard procedures.
The isocyanate dimer of Formula Ill can be prepared by reacting a compound of the formula:
with a molar excess of phosgene.
This reaction can be performed by adding a slurry or solution of the compound of Formula V in a suitable organic solvent, such as toluene, to a saturated solution of phosgene in an organic solvent, such as toluene. The resulting mixture can be stirred at ambient temperatures for a period of from about 4 to about 24 hours. This reaction mixture can then be purged with nitrogen gas to remove unreacted phosgene, followed by filtration, if the desired product forms as a precipitate, or by evaporation if the product is soluble therein. It can be used as recovered or further purified.
The following examples illustrate the preparations of the compounds of the present invention.
EXAMPLE 1
Preparation of 5-t-Butylisoxazol-3-yl-lsocyanate Dimer
A solution of phosgene (12%) in toluene (80 ml) was charged into a glass reaction vessel equipped with a mechanical stirrer. A slurry of 5-t-butyl-3-aminoisoxazole (4 grams) in toluene (20 ml) was added to the reaction vessel and the resulting mixture was stirred for a period of about 16 hours resulting in the formation of a precipitate. The reaction mixture was then purged with nitrogen gas to remove unreacted phosgene. The purged mixture was then filtered to recover the desired product, 5-t-butylisoxazol-3-yl isocyanate dimer as a solid.
EXAMPLE 2
Preparation of 1 -(54-Butylisoxazol-3-yI)-3-Meth yI-3-(1, 3-Dioxolan-2-ylmethyl) Urea.
A mixture of 5-t-butylisoxazol-3-yl isocyanate dimer (5 grams), N-(1 ,3-dioxolan-1-ylmethyl)me- thylamine (4 grams) and toluene (100 ml) were charged into a glass reaction flask equipped with a mechanical stirrer and thermometer. The reaction mixture was then warmed with stirring until the reactants dissolved.After this time the reaction mixture was stripped of solvent and the residue was recrystallized from ethyl acetate to yield the desired product as a solid having a melting point of 130-131 C. Its elemental analysis was:
C H N
% % %
Theoretical 55.11 7.47 14.83
Found 54.36; 54.56 7.47; 7.48 14.45; 14.52
EXAMPLE 3
Preparation of 1 -(54-Butylisoxazol-3-yI)-3-Meth yI-3-( 1, 3-Dioxan-2-ylmethyi) Urea
A mixture of 5-t-butylisoxazol-3-yl-isocyanate dimer (5 grams), N-(1,3-dioxan-2-ylmethyl)methylamine (4.5 grams) and toluene (100 ml) were charged into a glass reaction flask equipped with a mechanical stirrer and thermometer. The reaction mixture was then warmed with stirring until the reactants dissolved.Hexane (50 ml) was added to the reaction mixture and the desired product was recovered as the precipitate having a melting point of 171-173"C. Its elemental analysis was:
C H N
% % %
Theoretical 56.55 7.8 14.13
Found 55.79; 55.96 7.8; 7.94 13.85; 13.96
EXAMPLE 4
Exemplary of the compounds within the scope of the present invention that can be prepared by the procedures of the preceding examples are::
1 -3-#butylisoxazol-5-yl)-3-methyl-3-( 1, 3-d ioxolan-2-yl-methyl) urea
1 -(3- t-butyl isoxazol-5-yl)-3-methyl-3-( 1 , 3-dioxan-2-yl-methyl) urea
1 -(5-butylisoxazol-3-yl)-3-methyl-3-(4, 5-dimethyl- 1, 3-dioxolan-2-ylmethyl) urea (1 -(5-t-butylisoxazol-3-yl)-3-methyl-3-(4, 5, 6-triethyl- 1 , 3-dioxan-2-ylmethyl) urea
1 -(3-t-butylisoxazol-5-yl)-3-methyl-3-(4-hexyl- 1 , 3-dioxolan-2-ylmethyl) urea;
1 -(3-t-butylisoxazol-5-yl)-3-methyl-3-(5, 6-dipentyl- 1, 3 dioxan-2-ylmethyl) urea
1 -(5-t-butylisoxazol-3-yl)-3-methyl-3-(4-isopropyl- 1, 3-dioxolan-2-ylmethyl) urea;;
1 -(5-t-butylisoxazol-3-yl)-3-methyl-3-(4, 5-dibutyl- 1 , 3-dioxan-2-ylmethyl) urea 1-(3-t-butylisoxazol-5-yl)-3-methyl-3-(5-pentyl-1,3-dioXolan-2-ylmethyl) urea
1 -(3-Sbutylisoxazol-5-yl)--3-methyl-3-(4-methyl-5-ethyl- 1 , 3-dioxan-2-ylmethyl) urea
1 -(5-t-butylisoxazol-3-yl)-3-methyl-3-(4-ethyl-5-propyl- 1 3-dioxolan-2-ylmethyl) urea
1 -(5-t-butylisoxazol-3-yl)-3-methyl-3-(4-ethyl-5, 6-diisopropyl- 1 , 3-dioxan-2-ylmethyl) urea 1-(3- bbutylisoxazol-5-yl)-3-methyl-3-(4-hexyl-5-pentyl- 1 , 3-dioxolan-2-yl methyl) urea 1 -(3- t-butylisoxazol-5-yl)-3-methyl-3-(5-butyl-6-propyl- 1 3-dioxan-2-ylmethyl) urea For practical use as herbicides, the compounds of this invention are generally incoporated into herbicidal compositions which comprise an inert carrier and a herbicidally toxic amount of such a compound. Such herbicidal compositions, which can also be called formulations, enable the active compound to be applied conveniently to the site of the weed infestation in any desired quantity. These compositions can be solids such as dusts, granules, or wettable powders; or they can be liquids such as solutions, aerosols or emulsifiable concentrates.
For example, dusts can be prepared by grinding and blending the active compound with a solid inert carrier such as the talcs, clays, silicas, pyrophyllite and the like. Granular formulations can be prepared by impregnating the compound, usually dissolved in a suitable solvent, onto and into granulated carriers such as the attapulgites or the vermiculites, usually of a particle size range of from about 0.3 to 1.5 mm. Wettable powders which can be dispersed in water or oil to any desired concentration of the active compound can be prepared by incorporating wetting agents into concentrated dust compositions.
In some cases the active compounds are sufficiently soluble in common organic solvents such as kerosene or xylene so that they can be used directly as solutions in these solvents.
Frequently, solutions of herbicides can be dispersed under super-atmospheric pressure as aerosols. However, preferred liquid herbicidal compositions are emulsifiable concentrates, which comprise an active compound according to this invention and as the inert carrier, a solvent and an emulsifier. Such emulsifiable concentrates can be extended with water and/or oil to any desired concentration of active compound for application as sprays to the site of the weed infestation. The emulsifiers most commonly used in these concentrates are nonionic or mixtures of nonionic with anionic surface-active agents. With the use of some emulsifier systems an inverted emulsion (water in oil) can be prepared for direct application to weed infestation.
A typical herbicidal composition according to this invention is illustrated by the following example, in which the quantities are in parts by weight.
EXAMPLE 5
PREPARATION OF A DUST
Product of Example 2 10
Powdered Talc 90
The above ingredients are mixed in a mechanical grinder-blender and are ground until a homogeneous, free-flowing dust of the desired particle size is obtained. This dust is suitable for direct application to the site of the weed infestation.
The compounds of this invention can be applied as herbicides in any manner recognized by the art. One method for the control of weeds comprises contacting the locus of said weeds with a herbicidal composition comprising an inert carrier and, as an essential active ingredient in a quantity which is herbicidally toxic to said weeds, a compound of the present invention. The concentration of the new compounds of this invention in the herbicidal compositions will vary greatly with the type of formulation and the purpose for which it is designed, but generally the herbicidal compositions will comprise from 0.05 to about 95 percent by weight of the active compounds of this invention. In a preferred embodiment of this invention, the herbicidal compositions will comprise from about 5 to about 75 percent by weight of the active compound.The compositions can also comprise such additional substances as other pesticides, such as insecticides, nematocides, fungicides and the like; stabilizers, spreaders, deactivators, adhesives, stickers, fertilizers, activators, synergists and the like.
The compounds of the present invention are also useful when combined with other herbicides and/or defoliants, dessicants, growth inhibitors and the like in the herbicidal compositions heretobefore described. These other materials can comprise from about 5% to about 95% of the active ingredients in the herbicidal compositions. Use of combinations of these other herbicides and/or defoliants, dessicants, etc. with the compounds of the present invention provide herbicidal compositions of the individual herbicides.The other herbicides, defoliants, dessicants and the plant growth inhibitors, with which the compounds of this invention can be used in the herbicidal compositions to control weeds, can include chlorophenoxy herbicides such as 2,4-D, 2,4,5-T, MCPA, MCPB, 4(2,4-DB), 2,4-DEB, 4-CPB, 4-XPP, 2,4,5-TB, 2,4,5-TES, 3,4,-DA, silvex and the like; carbamate, herbicides such as IPC, Cl PC, swep, barban, BCPC,
CEPC, CPPC and the like; thiocarbamate and dithiocarbamate herbicides such as DCEC, methan sodium, EPTC, diallate, PEBC, perbulate, vernolate and the like; substituted urea herbicides such as norea, disuron, dichloral urea, chloroxuron, cycluron, fenuron, monuron, monuron TCA, diuron, linuron, molinuron, neburon, buturon; trimeturon and the like symmetrical triazine, herbicides such as simazine, chlorazine, atraone, desmetryne, norazine, ipazine, prometryn atrazine, trietazine, simetone, prometone, propazine, ametryne and the like; chloroacetamide herbicides such as alpha-chloro-N,n-dimethylacetamide, CD EA, CDAA, alpha-chloro-N-isopropylacetamide, 2-chloro-N-isopropyl-acetanilide, 4-(chloroacetyl)-morpholine, 1 -(chloroacetyl)piperidine and the like; chlorinated aliphatic acid herbicides such as TCA, dalapon, 2,3-dichloropropropionic acid, 2,2,3-TPA and the like; chlorinated benzoic acid and phenylacetic acid herbicides such as 2,3,6-TBA, 2,3,5,6-TBA, dicamba, tricamba, amiben, fenac, PBA, 2-methoxy-3,6dichlorophenylacetic acid, 3-methoxy-2, 6-dichlorophenylacetic acid, 2-methoxy-3, 4, 6-trichloro- phenylacetic acid, 2,4-dichloro-3-nitrobenzoic acid and the like; and such compounds as aminotriazole, maleic hydrazide, phenyl mercuric acetate, enothal, biuret, technical chlordane, dimethyl 2,3,5,6-tetrachloroterephthalate, diquat, erbon, DNC, DNBP, dichlorobenil, DPA, diphenamid, dipropalin, trifluraline, solan, dicryl, merphos, DMPA, DSMA, MSMA, potassium azide, acrolein, benefin, bensulide, AMS, bromacil, 2-(3,4-dichlorophenyl)-4-methyl-1 ,2,4-oxadi- azolidine, 3,5-dione, bromoxynil, cacodylic acid, DMA, DPMF, cypromid, DCB, DCPA, dichlone, diphenatril, DMTT, DNAP, EBEP, EXD, HCA, iosynil, IPX, isocril, potassium cyanate, MAA,
MAMA, MCPES, MCPP, MH, molinate, NPA, OCH paraquat, PCP, picloram, DPA, PCA, pyrichlor, sesone, terbacil, terbutol, TCBA, brominil, CP-50144, H-176-1, H-732, M-2091, planavin, dosium tetraborate, calcium cyanamid, DEF, ethyl xanthogen disulfide, sindone, sindone B, propanil and the like.
Such herbicides can also be used in the methods and composition of this invention in the form of their salts, esters, am ides, and other derivatives whenever applicable to the particular patent compound.
Weeds are undesirable plants growing where they are not wanted, having no economic value, and interfering with the production of cultivated crops, with the growing of ornamental plants, or with the welfare of livestock. Many types of weeds are known, including annuals such as pigweed, lambsquarter, foxtail, crabgrass, wild mustard, field pennycress, ryegrass, goose grass, chickweed, wild oats, velvet leaf, purselane, barnyard grass, smartweeds, knotweed, cocklebur, wild buckwheat, kochia, medic corn cockle, ragweed, sowthistle, coffee-weed, croton, cuphea, dodder, fumitory, groundsel, hemp nettle, knowel, spurge, spurry, emex, jungle rice, pondweed, dog fennel, carpetweed, morning glory, bedstraw, ducksalad and naiad; biennials such as wild carrot, matricaria, wild barley, campion, chamomile, burdock, mullein, roundleaved mallow, bull thistle, hounds-tongue, moth mullein and purple star thistle; or perennials such as white cockle, perennial rye-grass, quackgrass, Johnson grass, Canada thistle, hedge bindweed, Bermuda grass, sheep sorrel, curly dock, nutgrass, field chickweed, dandelion, campanula, field bindweed, Russian knapweed, mewquite, toadflaw, yarrow, aster, gromwell, horsetail, ironweed, sesbania, bulrush, cattail and wintercrass.
Similarly, such weeds can be classified as broadleaf or grassy weeds. It is economically desirable to control the growth of such weeds without damaging beneficial plants or livestock.
The new compounds of this invention are particularly valuable for weed control because they are toxic to many species and groups of weeds while they are relatively nontoxic to many beneficial plants. The exact amount of compound required will depend on a variety of factors, including the hardiness of the particular weed species, weather, type of soil, method of application, the kind of beneficial plants in the same area, and the like. Thus, while the application of up to only about one or two ounces of active compound per acre may be sufficient for good control of a light infestation of weeds growing under adverse conditions, the application of ten pounds or more of active compound per acre may be required for good control of a dense infestation of hardy perennial weeds growing under favourable conditions.
The herbicidal toxicity of the new compounds of this invention can be illustrated by many of the established testing techniques known to the art, such as pre- and post-emergence testing.
EXAMPLE 6
The herbicidal activity of the compounds of this invention was demonstrated by experiments carried out for the pre-emergence control of a variety of weeds. In these experiments small plastic greenhouse pots filled with dry soil were seeded with the various weed seeds. Twentyfour hours or less after the seeding, the pots were sprayed with water until the soil was wet and the test compounds formulated as aqueous emulsions of acetone solutions containing emulsifiers were sprayed at the indicated concentrations on the surface of the soil.
After spraying, the soil containers were placed in the greenhouse and provided with supplementary heat as required and daily or more frequent watering. The plants were maintained under these conditions for a period of from 14 to 21 days, at which time the condition of the plants and the degrees of injury to the plants was rated on a scale of from 0 to 10, as follows: 1 = no injury; 1,2 = slight injury; 3,4 = moderate injury; 5,6-moderately severe injury; 7,8,9 = severe injury, and 10 = death. The effectiveness of these compounds is demonstrated by the following data:
PRE-EMERGENCE HERBICIDE TEST DATA
14 DAYS AFTER TREATMENT
Product of Example 2
RATE OF
APPLICATION (Lbs/Acre) 1 0.5 0.25 0.125
Wild Mustard 10 1 10 5
Bindweed 8 5 5 4
Pigweed 8 0 0 0
Vlevet Leaf 8 0 0 0
Morning Glory 10 10 8 8
Yellow Foxtail 7 3 3 0
Barnyard Grass 9 0 0 0
Johnson Grass 8 8 7 8
Quack Grass 3 1 0 0
Wild Oats 7 4 3 0
Crabgrass 9 9 8 8
Sprangletop 9 9 8 5
Cheat grass 0 0 0 0
Sugar Beet 10 0 10 10
Soybean 7 3 2 2
Cotton NE O 0 0
Pinto Bean O 0 0 0
Alfalfa 10 10 10 5
Wheat 5 0 0 0
Rice 10 8 7 7
Shorghum 8 7 2 2
Corn 6 5 3 0
Oats 5 7 0 0
PRE-EMERGENCE HERBICIDE TEST DATA 21 DAYS AFTER TREATMENT
Product of Example 2
RATE OF
APPLICATION (Lbs/Acre) 1 0.5 0.25 0.125
Wild Mustard 10 3 10 7
Bindweed 10 0 0 0
Pigweed 10 10 10 0
Velvet Leaf 10 2 9 1
Morning Glory 10 10 10 7
Yellow Foxtail 10 0 0 0
Barnyard Grass 10 0 0 0
Johnson Grass 9 8 5 3
Quack Grass 5 8 0 0
Wild Oats 10 10 8 0
Crabgrass 10 10 8 0
Sprangletop 10 10 9 0
Cheatgrass 8 8 1 0
Sugar Beet 10 10 10 10
Soybean 10 3 2 0
Cotton NE O 0 0
Pinto Bean 9 10 0 0
Alfalfa 10 10 10 0
Wheat 10 10 5 0
Rice 10 10 4 2
Sorghum 8 8 1 0
Corn 7 8 0 0
Oats 10 10 1 0
PRE-EMERGENCE HERBICIDE TEST DATA 14 DAYS AFTER TREATMENT
Product of Example 3
RATE OF
APPLICATION (Lbs/Acre) 4 2 1 0.5 0.25 0.125
Yellow Nutsedge 3 1 1 - - -
Wild Mustard 10 10 10 10 7 2
Bindweed - - 10 10 10 3
Pigweed 6 5 7 10 10 0
Jimsonweed 3 4 2 10 7 6
Velvet Leaf 3 10 10 9 9 1
Morning Glory 4 4 4 10 8 2
Yellow Foxtail 4 4 2 1 0 0
Barnyard Grass 10 8 3 0 0 0
Johnson Grass 3 6 2 0 0 0
Quack Grass - - 3 2 3 0
Wild Oats 5 7 7 0 0 0
Crabgrass 10 7 5 0 0 0
Sprangletop - - 9 1 0 0
Cheat Grass 3 0 0 8 0 0
Sugar Beet - - 10 10 10 10
Soybean - - 3 0 0 0
Cotton - - 10 10 10 9
Pinto Bean - - 1 0 0 0
Alfalfa - - 10 10 10 10
Wheat - - 10 10 0 0
Rice - - 0 0 0 0
Sorghum - - 2 0 0 0
Corn - - 2 0 0 0
Oats - - 7 0 0 0
PRE-EMERGENCE HERBICIDE TEST DATA 21 DAYS AFTER TREATMENT
Product of Example 3
RATE OF
APPLICATION (Lbs/Acre) 4 2 1 0.5 0.25 0.125
Yellow Nutsedge 3 2 2 -
Wild Mustard 10 10 10 10 10 10
Bindweed - - 10 10 10 7
Pigweed 7 8 8 10 10 0
Jimsonweed 10 10 5 10 10 10
Velvet Leaf 10 10 10 10 10 10
Morning Glory 10 10 10 10 10 10
Yellow Foxtail 10 10 10 1 0 0
Barnyard Grass 10 10 8 1 0 0
Johnson Grass 7 8 7 2 0 0
Quack Grass - - 10 10 7 0
Wild Oats 10 10 10 1 1 0
Crabgrass 10 10 10 0 0 0
Sprangletop - - 10 7 0 0
Cheat Grass 10 9 4 9 0 0
Sugar Beet - - 10 10 10 10
Soybean - - 10 10 4 1
Cotton - - 10 10 10 10
Pinto Bean - - 10 8 7 0
Alfalfa - - 10 10 10 10
Wheat - - 10 10 3 1
Rice - - 10 0 0 0
Sorghum - - 10 1 0 0
Corn - - 10 3 0 0
Oats - - 10 4 0 0
The herbicidal activity of the compounds of this invention was also demonstrated by experiments carried out for the post-emergence control of a variety of weeds.In these experiments the compounds to be tested were formulated as aqueous emulsions and sprayed at the indicated dosage on the foliage of the various weed species that have attained a prescribed size. After spraying, the plants were placed in a greenhouse and watered daily or more frequently. Water was not applied to the foliage of the treated plants. The severity of the injury was determined 14 days after treatment and was rated on the scale of from 0 to 10 heretobefore described.The effectiveness of these compounds is demonstrated by the following data:
POST-EMERGENCE HERBICIDE TEST DATA
Product of Example 2
RATE OF
APPLICATION (Lbs/Acre) 1 0.5 0.25 0.125
Wild Mustard 10 10 10 10
Bindweed 10 10 10 10
Pigweed - - 10 10
Jimsonweed 10 10 10 10
Velvet Leaf 10 10 10 10
Morning Glory 10 10 10 10
Yellow Foxtail 8 9 5 0
Barnyard Grass 10 10 0 0
Johnson Grass 10 10 1 0
Quack Grass 10 10 10 0
Wild Oats 10 10 10 2
Crabgrass 10 8 0 0
Sprangletop 10 10 10 1
Cheat Grass 10 8 0 0
Sugar Beet 10 10 10 10
Cotton 10 10 10 10
Soybeans 10 10 7 6
Pinto Beans 10 10 10 7
Alfalfa 10 10 10 10
Sorghum 10 3 0 0
Wheat 10 10 10 5
Rice 10 10 10 1
Corn 10 7 0 0
Oats 10 10 9 1
POST-EMERGENCE HERBICIDE TEST DATA
Product of Example 3
RATE OF
APPLICATION (Lbs/Acre) 4 2 1 0.5 0.25 0.125 0.062 0.032
Yellow Nutsedge 10 7 8 10 10 10 - -
Wild Mustard 10 10 10 - - 10 0 0
Bindweed 10 7 7 10 7 0 0 0
Pigweed 10 10 10 10 10 10 -
Jimsonweed 10 10 10 10 10 10 0 0
Velvet Leaf - - - - 0 0 0
Morning Glory 10 10 10 10 10 10 0 0
Yellow Foxtail 7 10 9 10 0 0
Barnyard Grass 10 10 7 10 10 0 0 0
Johnson Grass 10 8 10 10 0 0 0 0
Quack Grass - - 7 7 0 0 - -
Wild Oats 10 10 10 1 0 0 -
Crabgrass 10 10 10 5 0 0 -
Sprangletop - - 10 7 0 0 -
Cheat Grass - - 3 1 0 0 -
Sugar Beets - - 10 10 10 10 - -
Cotton - - 10 10 10 10 -
Soybeans 10 10 10 9 1 1 0 0
Pinto Beans - - 10 10 10 0 -
Alfalfa - - 10 10 10 10 -
Sorghum - - 10 1 0 0 -
Wheat - - 10 10 0 0 -
Rice - - 0 0 0 0 - -
Corn - - 10 1 1 0 -
Oats - - 10 5 0 0 - -
Claims (11)
1. A compound of the formula:
wherein R is lower alkyl;
n is 0 or 1; and
m is 0 or an integer from 1 to 6.
2. A compound of the formula: wherein R, m and n have the meanings given in claim 1.
3. 1 -(5-t-butylisoxazol-3-yl)-3-methyl-3-( 1 , 3-dioxolan-2-ylmethyl) urea.
4. 1 (5-t-butylisoxazol-3-yl)-3-methyl-3-( 1 , 3-dioxan-2-ylmethyl) urea.
5. A compound as claimed in claim 1, substantially as hereinbefore described in any one of
Examples 1 to 4.
6. A method of preparing a compound as claimed in claim 1, which comprises reacting a compound of the formula:
with two molar amounts of an amine of the formula:
7. A method of preparing a compound as claimed in claim 1, substantially as hereinbefore described in any one of Examples 1 to 4.
8. A herbicidal composition comprising an'inert carrier and, as an essential ingredient in a quantity toxic to weeds, a compound as claimed in any one of claims 1 to 5.
9. A herbicidal composition substantially as hereinbefore described in Example 5 or 6.
10. A method of controlling weeds which comprises contacting said weeds with a compound as claimed in any one of claims 1 to 5 or a herbicidal composition as claimed in claim 8 or 9.
11. A method of controlling weeds substantially as hereinbefore described in Example 6.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38339182A | 1982-06-01 | 1982-06-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8310916D0 GB8310916D0 (en) | 1983-05-25 |
| GB2121034A true GB2121034A (en) | 1983-12-14 |
| GB2121034B GB2121034B (en) | 1986-02-05 |
Family
ID=23512920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08310916A Expired GB2121034B (en) | 1982-06-01 | 1983-04-22 | Herbicidal urea derivatives of isoxazole |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS58219185A (en) |
| KR (1) | KR860000849B1 (en) |
| AU (1) | AU555665B2 (en) |
| BE (1) | BE896883A (en) |
| BR (1) | BR8302575A (en) |
| CA (1) | CA1189512A (en) |
| CH (1) | CH654006A5 (en) |
| DD (1) | DD211943A5 (en) |
| DE (1) | DE3319557A1 (en) |
| DK (1) | DK246383A (en) |
| ES (1) | ES8407044A1 (en) |
| FR (1) | FR2527607A1 (en) |
| GB (1) | GB2121034B (en) |
| GR (1) | GR78262B (en) |
| IT (1) | IT1172261B (en) |
| NL (1) | NL8301659A (en) |
| NO (1) | NO831952L (en) |
| NZ (1) | NZ203871A (en) |
| PH (1) | PH19467A (en) |
| RO (1) | RO87127A (en) |
| SE (1) | SE8302972L (en) |
| SU (1) | SU1209019A3 (en) |
| YU (1) | YU117583A (en) |
| ZA (1) | ZA832937B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4507145A (en) * | 1980-02-19 | 1985-03-26 | Ppg Industries, Inc. | Herbicidal 3-[substituted 3- or 5-isoxazolyl]-1-4-, or 5-substituted-2-imidazolidinones |
-
1983
- 1983-04-08 CA CA000425522A patent/CA1189512A/en not_active Expired
- 1983-04-13 NZ NZ203871A patent/NZ203871A/en unknown
- 1983-04-22 GB GB08310916A patent/GB2121034B/en not_active Expired
- 1983-04-26 ZA ZA832937A patent/ZA832937B/en unknown
- 1983-04-26 KR KR1019830001763A patent/KR860000849B1/en active IP Right Grant
- 1983-04-27 CH CH2261/83A patent/CH654006A5/en not_active IP Right Cessation
- 1983-05-02 PH PH28842A patent/PH19467A/en unknown
- 1983-05-10 NL NL8301659A patent/NL8301659A/en not_active Application Discontinuation
- 1983-05-17 BR BR8302575A patent/BR8302575A/en unknown
- 1983-05-23 SU SU833595055A patent/SU1209019A3/en active
- 1983-05-24 IT IT48358/83A patent/IT1172261B/en active
- 1983-05-26 ES ES522736A patent/ES8407044A1/en not_active Expired
- 1983-05-26 SE SE8302972A patent/SE8302972L/en not_active Application Discontinuation
- 1983-05-26 YU YU01175/83A patent/YU117583A/en unknown
- 1983-05-30 GR GR71505A patent/GR78262B/el unknown
- 1983-05-30 DE DE19833319557 patent/DE3319557A1/en not_active Withdrawn
- 1983-05-30 BE BE0/210876A patent/BE896883A/en not_active IP Right Cessation
- 1983-05-30 FR FR8308927A patent/FR2527607A1/en not_active Withdrawn
- 1983-05-31 DK DK246383A patent/DK246383A/en not_active Application Discontinuation
- 1983-05-31 DD DD83251540A patent/DD211943A5/en unknown
- 1983-05-31 AU AU15217/83A patent/AU555665B2/en not_active Expired - Fee Related
- 1983-05-31 NO NO831952A patent/NO831952L/en unknown
- 1983-05-31 RO RO83111130A patent/RO87127A/en unknown
- 1983-06-01 JP JP58097779A patent/JPS58219185A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2527607A1 (en) | 1983-12-02 |
| SE8302972L (en) | 1983-12-02 |
| KR840005136A (en) | 1984-11-03 |
| DK246383A (en) | 1983-12-02 |
| DE3319557A1 (en) | 1983-12-01 |
| GB2121034B (en) | 1986-02-05 |
| NZ203871A (en) | 1985-05-31 |
| IT1172261B (en) | 1987-06-18 |
| DD211943A5 (en) | 1984-08-01 |
| JPS58219185A (en) | 1983-12-20 |
| CA1189512A (en) | 1985-06-25 |
| IT8348358A0 (en) | 1983-05-24 |
| KR860000849B1 (en) | 1986-07-09 |
| SU1209019A3 (en) | 1986-01-30 |
| BE896883A (en) | 1983-09-16 |
| NO831952L (en) | 1983-12-02 |
| BR8302575A (en) | 1984-01-17 |
| AU555665B2 (en) | 1986-10-02 |
| PH19467A (en) | 1986-05-14 |
| CH654006A5 (en) | 1986-01-31 |
| RO87127A (en) | 1985-12-20 |
| AU1521783A (en) | 1984-01-19 |
| YU117583A (en) | 1986-12-31 |
| ES522736A0 (en) | 1984-09-01 |
| DK246383D0 (en) | 1983-05-31 |
| SE8302972D0 (en) | 1983-05-26 |
| ZA832937B (en) | 1984-01-25 |
| RO87127B (en) | 1985-12-01 |
| ES8407044A1 (en) | 1984-09-01 |
| GR78262B (en) | 1984-09-26 |
| NL8301659A (en) | 1984-01-02 |
| GB8310916D0 (en) | 1983-05-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |