CA1189512A - Urea compositions of matter - Google Patents
Urea compositions of matterInfo
- Publication number
- CA1189512A CA1189512A CA000425522A CA425522A CA1189512A CA 1189512 A CA1189512 A CA 1189512A CA 000425522 A CA000425522 A CA 000425522A CA 425522 A CA425522 A CA 425522A CA 1189512 A CA1189512 A CA 1189512A
- Authority
- CA
- Canada
- Prior art keywords
- urea
- compounds
- grass
- methyl
- butylisoxazol
- 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.)
- Expired
Links
Classifications
-
- 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
Abstract
ABSTRACT OF THE DISCLOSURE
This application discloses urea compounds of the formula:
or wherein R is lower alkyl;
n is 0 or 1; and m is 0 or an integer from 1 to 6.
The disclosed compounds are useful as herbicides.
This application discloses urea compounds of the formula:
or wherein R is lower alkyl;
n is 0 or 1; and m is 0 or an integer from 1 to 6.
The disclosed compounds are useful as herbicides.
Description
5~2 ~37 NEW UREA COMPOSITIONS OF MATTER
This invention relates to new chemical composi~ions of matter and more specifically ~o new urea compounds of the for-mulas:
C~ 3 ~H--C--N--cn2--C ~=
H C--C
or , ~ H3 / ~IH2~n CH3 O - \ C
~ H C - F - N
c~3 (I) wherein R is lower aikyl9 n is 0 or 1 and ~ -m is 0 or an integer fro~ 1 to 6~ .
The preferred compounds have ~he s~ructural formula:.
25 ~ N - C -N - C~2-C _ ~ (CH2)n C11~3 0 \--C
~13C - C ~ / N
C~3 (II) The compounds of ~he presen~ invention are particularly useful as herbicides.
The ~erm "lower" 85 used herein designates a straight or branched carbon chain of up to six carbon atomsO
'' ~
~ 9S ~ 2 .
The compounds of the present invention can be prepared by reac*ing a compound of the formula:
r O-~=N~
~ N CH;
or is ~ o=c nr~
N C ~ CH3 _ 2 (III) wi~h two molar amounts of an amine of the formula:
" /~F
CH3 \o~
This reaction can be effected by heating a mixture of ths 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 th~ solvent and can be further purified by standard procedures.
The isocyanate dimer of Formula III can be prepared by reacting a compound of ~he formula:
.
s~
CH3 ~ NM2 CH3 ~ NH2 H3C - C ~ / N or ~H3 ~
(V) with a molar excess of phosgsneO
This reaction can be performed by adding a slurry o~
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 hoursO This reaction mixture can then be purged with nitrogen gas to remove unreacted phosgene~ followed by filtration, if the desired product forms as a precipita*e, 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 l PREYARATION OF 5-t-Butylisoxazol-3-~
ISOCYANATE 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 ~1~ was added to the reaction vessel and the re-sulting mixture was stirred for a period of about 16 hours resulting in the formation of a precipita~e. The reaction mixture was ~hen purged with nitrogen gas to remove unreacted phosgene. The purged mixture was then filtered ~o recover the desired product, 5-t-butylisoxazol-3-yl isocyanate dimer as a solid.
PREPARATION~ lisoxazol-3~x13 -3-Methyl-3 `
A mixture of S-t-butylisoxazol-3-yl isocyanate dimPr (5 gTams) r N-(1,3-dioxolan-2-ylmethyl)methylamine (4 grams) and toluene (100 ml) were charged into a glass reaction flask equipped with a mechanical stirrer and thermometer. The reac-tion mixture was then warmed with stirring until the reactantsdissolved. After this ~ime ~he reaction mixture was stripped of solvent and the residue was recrystallized from ethyl ace-tate ~o yield the desired product as a solid having a ~elting point of 130 - 131C. Its elemental analysis was:
C H N
%
Theoretical 55.11 7.47 14.83 Found 54.36; 54~56 7L47; 7.4814.45; 14.52 EXA~PLE 3 PREPARATION OF 1-~5-t-But lisoxazol-3- 1)-3-Meth 1-3-- Y y y _ _ (1,3-Dioxan-2-ylmethyl~ Urea A mixture of 5-t-butylisoxazol-3-yl-isocyanate dimer (5 grams), N-~1,3-dioxan-2-ylmethyl)methylamine ~4O5 grams) and toluene ~100 ml) were charged into a glass reaction flask equipped with a mechanical stirrer and thermometerO The reac-tion mixture was then warmed with stirring until the reactants dissolved. Hexane (50 ml~ was added ~o the reaction mixture and the desired product was recovered as the precipitate having a melting point of 171 - 173C. Its elemental analysis was:
C H N
~ ~
Theoretical 56~55 7.8 14.13 Found 55.79; 55.9S 7,8; 7.94 13.85; 13.96 Exemplary of the compounds within the scope of the present invention that can be prepared by the procedures o the preceding examples areo 1~3-t-butylisoxazol-5-yl)-3-me~hyl-3-~1,3~dioxolan 2 yl-methyl) urea 1-~3~t-butylisoxazol-5-yl)-3-methyl~3-~1,3-dioxan-2-yl-.4_ l' -,t~
methyl~ urea 1-(5-t-butylisoxazol-3-yl~-3-methyl-3-(4,5-dime'chyl-193-dioxolan-2-ylmethyl~ urea 1-(5-t-butylisoxazol-3-yl)-3-methyl-3-(4,5,6 triethyl-I,3-dioxan-2-ylmethyl) urea 1-~3-t-butylisoxazol-5-yl)-3-methyl-3-(4-hexyl~ dioxolan
This invention relates to new chemical composi~ions of matter and more specifically ~o new urea compounds of the for-mulas:
C~ 3 ~H--C--N--cn2--C ~=
H C--C
or , ~ H3 / ~IH2~n CH3 O - \ C
~ H C - F - N
c~3 (I) wherein R is lower aikyl9 n is 0 or 1 and ~ -m is 0 or an integer fro~ 1 to 6~ .
The preferred compounds have ~he s~ructural formula:.
25 ~ N - C -N - C~2-C _ ~ (CH2)n C11~3 0 \--C
~13C - C ~ / N
C~3 (II) The compounds of ~he presen~ invention are particularly useful as herbicides.
The ~erm "lower" 85 used herein designates a straight or branched carbon chain of up to six carbon atomsO
'' ~
~ 9S ~ 2 .
The compounds of the present invention can be prepared by reac*ing a compound of the formula:
r O-~=N~
~ N CH;
or is ~ o=c nr~
N C ~ CH3 _ 2 (III) wi~h two molar amounts of an amine of the formula:
" /~F
CH3 \o~
This reaction can be effected by heating a mixture of ths 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 th~ solvent and can be further purified by standard procedures.
The isocyanate dimer of Formula III can be prepared by reacting a compound of ~he formula:
.
s~
CH3 ~ NM2 CH3 ~ NH2 H3C - C ~ / N or ~H3 ~
(V) with a molar excess of phosgsneO
This reaction can be performed by adding a slurry o~
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 hoursO This reaction mixture can then be purged with nitrogen gas to remove unreacted phosgene~ followed by filtration, if the desired product forms as a precipita*e, 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 l PREYARATION OF 5-t-Butylisoxazol-3-~
ISOCYANATE 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 ~1~ was added to the reaction vessel and the re-sulting mixture was stirred for a period of about 16 hours resulting in the formation of a precipita~e. The reaction mixture was ~hen purged with nitrogen gas to remove unreacted phosgene. The purged mixture was then filtered ~o recover the desired product, 5-t-butylisoxazol-3-yl isocyanate dimer as a solid.
PREPARATION~ lisoxazol-3~x13 -3-Methyl-3 `
A mixture of S-t-butylisoxazol-3-yl isocyanate dimPr (5 gTams) r N-(1,3-dioxolan-2-ylmethyl)methylamine (4 grams) and toluene (100 ml) were charged into a glass reaction flask equipped with a mechanical stirrer and thermometer. The reac-tion mixture was then warmed with stirring until the reactantsdissolved. After this ~ime ~he reaction mixture was stripped of solvent and the residue was recrystallized from ethyl ace-tate ~o yield the desired product as a solid having a ~elting point of 130 - 131C. Its elemental analysis was:
C H N
%
Theoretical 55.11 7.47 14.83 Found 54.36; 54~56 7L47; 7.4814.45; 14.52 EXA~PLE 3 PREPARATION OF 1-~5-t-But lisoxazol-3- 1)-3-Meth 1-3-- Y y y _ _ (1,3-Dioxan-2-ylmethyl~ Urea A mixture of 5-t-butylisoxazol-3-yl-isocyanate dimer (5 grams), N-~1,3-dioxan-2-ylmethyl)methylamine ~4O5 grams) and toluene ~100 ml) were charged into a glass reaction flask equipped with a mechanical stirrer and thermometerO The reac-tion mixture was then warmed with stirring until the reactants dissolved. Hexane (50 ml~ was added ~o the reaction mixture and the desired product was recovered as the precipitate having a melting point of 171 - 173C. Its elemental analysis was:
C H N
~ ~
Theoretical 56~55 7.8 14.13 Found 55.79; 55.9S 7,8; 7.94 13.85; 13.96 Exemplary of the compounds within the scope of the present invention that can be prepared by the procedures o the preceding examples areo 1~3-t-butylisoxazol-5-yl)-3-me~hyl-3-~1,3~dioxolan 2 yl-methyl) urea 1-~3~t-butylisoxazol-5-yl)-3-methyl~3-~1,3-dioxan-2-yl-.4_ l' -,t~
methyl~ urea 1-(5-t-butylisoxazol-3-yl~-3-methyl-3-(4,5-dime'chyl-193-dioxolan-2-ylmethyl~ urea 1-(5-t-butylisoxazol-3-yl)-3-methyl-3-(4,5,6 triethyl-I,3-dioxan-2-ylmethyl) urea 1-~3-t-butylisoxazol-5-yl)-3-methyl-3-(4-hexyl~ 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-butylisoxa~ol-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-dioxo-lan-2-ylmethyl) urea - 1-(3-t-butylisoxazol-5-yl)-3-methyl-3-(4-methyl-5-ethyl-1,3-dioxan-2-ylmethyl) urea 1-~5-t-butylisoxa~ol-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-576-diiso-propyl-1,3-dioxan-2-ylmethyl) urea 1-(3-t-butylisoxazol-5-ylj-3-methyl-3-(4-hexyl-5-pentyl-1,3 -dioxolan-2-ylmethyl) 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 in-vention are generally incorporated 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 con-veniently to the site of the weed infestation in any desired quan-tity. These compositions can be solids such as dusts7 granules, or wettable powders; or they can be liquids such as solutions, aerosols or emulsifiable concentrates.
~5-~ 3~ ~ ~
For example, dusts can be prepared by grinding and blending the active compound with a solid inert carrier s~ch 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 ~o 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 in~o concentrated dust compositions.
In some cases the ac~i~e 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. Prequently, solutions of herbicides can be dispersed under superatmospheric pressure as aerosols. However, preferred liquid herbicidal compo-sitions are emulsifiable concentrates, which comprise an active com-pound 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 ~ith anionic surface active agents, With the use of some emulsifier systems an inYerted 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, PREPARATION OF A DUST
Product of Example 2 l0 Powdered Talc 90 The above ingredients are mixed in a mechanical grinder-blender and are ground until a homogeneous 9 free-flowing dust of th~
desired particle size is obtal ed. 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 manr,er recognized by the art. One method for the con~rol 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 o~ the new compounds of this in~ention in the herbicidal compositions will ~ary greatly with the type o~ fDrmulation and the purpose or which it is designed, but generally the herbicidal compositions will comprise ~rom 0.05 to about 9~ percent by weight of the active compounds o~
this invention. In a preferred embodimen~ of this invention, the herbicidal compositions will comprise from a~out 5 to about 75 percent by weight of the active compound. The compositions can also comprise such additional substances as other pesticides7 such as insecticides, nematocides, fungicides and the like; stabili~ers, spreaders, deae~i-vators, 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 heFbicidal 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 com-positlons of the individual herbicides. The other herbicides, de-foliants, 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 chIorophenoxy herbicides such as 2,4-D, 2,4,5-T, MCPA, MCPB, 4(2,4-DB), 2,4-DEB, 4-CPB, 4-XPP7 2,4,5-TB, 2,4,5-TES 9 3,4,-DA, silvex and the like; carbama~e, herbicides such as IPC, CIPC, swep, barban, BCPC, CEPC, CPPC and khe like;
thiocarbamate and dithiocarbamate herbicides such as DCECg methan _~_ sodium, EPTC, di.allate, pEsc, perbula-te, ~ernolate and the like; subs-ti-tuted urea herbicides such as norea, disuron, dichloral urea, chloroxuron, cycluron, fenuron, monuron, nonuron TCA, diuron, linuron, molinuron, neburon~
bu-turon; trime-turon and the like symmetrical triazine, herbicides such as simazine, chlorazine, atraone, des-me~ryne, norazine, ipazine, prometryn atrazine, trietazine, simetone, prometone, propazine, ame-tryne and the like;
chloroacetamide herbicides such as alpha-chloro-Nrn-dimethylacetamide, CDEAr CDAA~ alpha-chloro~N-i~opropyl-acetamider 2-chloro-N-isopropyl-acetanilide, 4-(chloro-acetyl)morpholine, l-(chloroacetyl)piperidine and the like; chlorinated aliphatic acid herbicides such as TCA, dalapon, 2,3-dichloropropropionic acid, 2,2,3-TP~ and the. like; chlorinated benzoic acid and phenylace-tic acid herbicides such as 2,3 r6-TBA1 2,3,5, 6-TBA, dicamba~
tricamba, amiben, fenac, PBA~ 2-methoxy-3,6-dichlorophenyl-acetic acid, 3-methoxy-2l6-dichlorophenylace~ic acid, 2-methoxy-3,4,6-trichlorophenylacetic acid, 2j4-dichloro-
~5-~ 3~ ~ ~
For example, dusts can be prepared by grinding and blending the active compound with a solid inert carrier s~ch 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 ~o 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 in~o concentrated dust compositions.
In some cases the ac~i~e 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. Prequently, solutions of herbicides can be dispersed under superatmospheric pressure as aerosols. However, preferred liquid herbicidal compo-sitions are emulsifiable concentrates, which comprise an active com-pound 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 ~ith anionic surface active agents, With the use of some emulsifier systems an inYerted 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, PREPARATION OF A DUST
Product of Example 2 l0 Powdered Talc 90 The above ingredients are mixed in a mechanical grinder-blender and are ground until a homogeneous 9 free-flowing dust of th~
desired particle size is obtal ed. 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 manr,er recognized by the art. One method for the con~rol 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 o~ the new compounds of this in~ention in the herbicidal compositions will ~ary greatly with the type o~ fDrmulation and the purpose or which it is designed, but generally the herbicidal compositions will comprise ~rom 0.05 to about 9~ percent by weight of the active compounds o~
this invention. In a preferred embodimen~ of this invention, the herbicidal compositions will comprise from a~out 5 to about 75 percent by weight of the active compound. The compositions can also comprise such additional substances as other pesticides7 such as insecticides, nematocides, fungicides and the like; stabili~ers, spreaders, deae~i-vators, 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 heFbicidal 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 com-positlons of the individual herbicides. The other herbicides, de-foliants, 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 chIorophenoxy herbicides such as 2,4-D, 2,4,5-T, MCPA, MCPB, 4(2,4-DB), 2,4-DEB, 4-CPB, 4-XPP7 2,4,5-TB, 2,4,5-TES 9 3,4,-DA, silvex and the like; carbama~e, herbicides such as IPC, CIPC, swep, barban, BCPC, CEPC, CPPC and khe like;
thiocarbamate and dithiocarbamate herbicides such as DCECg methan _~_ sodium, EPTC, di.allate, pEsc, perbula-te, ~ernolate and the like; subs-ti-tuted urea herbicides such as norea, disuron, dichloral urea, chloroxuron, cycluron, fenuron, monuron, nonuron TCA, diuron, linuron, molinuron, neburon~
bu-turon; trime-turon and the like symmetrical triazine, herbicides such as simazine, chlorazine, atraone, des-me~ryne, norazine, ipazine, prometryn atrazine, trietazine, simetone, prometone, propazine, ame-tryne and the like;
chloroacetamide herbicides such as alpha-chloro-Nrn-dimethylacetamide, CDEAr CDAA~ alpha-chloro~N-i~opropyl-acetamider 2-chloro-N-isopropyl-acetanilide, 4-(chloro-acetyl)morpholine, l-(chloroacetyl)piperidine and the like; chlorinated aliphatic acid herbicides such as TCA, dalapon, 2,3-dichloropropropionic acid, 2,2,3-TP~ and the. like; chlorinated benzoic acid and phenylace-tic acid herbicides such as 2,3 r6-TBA1 2,3,5, 6-TBA, dicamba~
tricamba, amiben, fenac, PBA~ 2-methoxy-3,6-dichlorophenyl-acetic acid, 3-methoxy-2l6-dichlorophenylace~ic acid, 2-methoxy-3,4,6-trichlorophenylacetic acid, 2j4-dichloro-
3-nitrobenzoic acid and the like; and such compounds as aminotriazole, maleic hydrazide, phenyl mercuric acetate~
endothal, biuretl technical chlordanel dimethyl 2,3,5,6-tetrachloroterephthalate, diquat, erbon, DNC, DNBP, dichlorobenil, DPA, diphenamia, dipropalin, trifluraline, solan, dicryl, merphos, DMPAI DSMA, MSMh, potassium azide~
acrolein, benefin, bensulide, AMS, bromacil, 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine, 3,5-dione, bromoxynil, cacodylic acid, DMA, DPMF, cypromid, DCB, DCPA, dichlone, diphenatril, DMTT~ DNAP~ EBEPt EXD~
HCA, iosynil, IPX, isocril, potassium cyanate~ MAA, MAMA, MCPES, MCPP, MH, molinate, NPA, OC~I paraquat, PCPf picloram, DPA~ PCA, pyrichlor, sesone, terbac.il, 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 li~e.
.,~ _ ~ _ ~ mab/ ~
~$~
Such herbicides can also be used in the methods and composition of this invention in the form of their salts, esters, amides, and otheT derivatives whenever applicable to ~he par-ticular 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 ~ypes of weeds are known, including annuals such as pigweed9 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, dodder9 fumitory, groundsel~ hemp nettle, knowel, spurge, spurry, emex, jungle rice, pondweed, dog fennel, carpetweed, morning glory, bedstraw, ducksalad and naîad; 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 chick-weed, dandelion, campanula, field bindweed, Russian knapweed, mewquite, toadflax, yarrow, as~er, gromwell, horsetail, iron-weed, 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 ~his invention are particularly valuable for weed control because ~hey are toxic to many speci s and groups of weeds while they are relatively non~oxic ~o many beneficial plants. The exact amount of compound required will _g_ depend on a variety of factors, including the hardiness of the particular weed species, weather9 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 favorable conaitions.
The herbicidal toxicity of the new compounds of this invention can be illustrated by many of the es~ablished testing techniques known to the art, such as pre- and post emergence testing. ~
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 experi-ments small plastic greenhouse pots filled with dry soil were seeded with the various weed seeds. Twenty-four 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 so:Lutions containing emulsifiers were sprayed at the indicated concen~rations 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 frequently watering. The plants were main-tained under these conditions for a period of from 14 ~o 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, lp2 = slight injury, 3,4 = moderate injury3 556 = moderately severe injury~ 7,8,9 ~ seYere injury, and 10 = deathO The effectiveness of these compounds is demon stra~ed by the following data:
,_ ,. .
Produ_t of Ex mple 2 RATE OF
APPLICATION
~Lbs/Acre) 1 0.5 0.25 0.125 Wild Mustard 10 1 10 5 Bindweed 8 5 S 4 Pigweed 8 0 0 0 Velvet 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 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 0 0 0 Pinto Bean 0 0 0 0 Alfalfa 10 10 10 5 Wheat . 5 Rice 10 8 7 7 Sorghum 8 7 2 2 Corn 6 S 3 0 Oats 5 7 0 0 .. ~
Product of Example_2 -RATE OF
APPLICATION
(Lbs/Acre) 1 0.5 0.25 0.125 Wild Mustard 10 3 10 7 BiDdweed 10 O O 0 Pigweed 10 10 10 O
Velvet l.eaf 10 2 9 Morning Glory10 10 l0 7 Yellow Foxtail 10 O 0 0 Barnyard Grass l0 0 0 O
Johnson Grass 9 8 5 3 Quack Grass 5 8 0 0 Wild Oats lO 10 8 0 Crabgrass l0 10 8 O
Sprangletop 10 10 9 O
Cheat Grass 8 8 Sugar Beet 10 10 10 10 Soybean 10 3 2 0 Cot~on NE 0 O O
PintG Bean 9 10 0 O
Alfalfa 10 10 10 0 Wheat l0 lO 5 0 Rice 10 10 4 2 Sorghum 8 8 1 0 Corn 7 ~
9ats 10 10 1 O
-12~ , ~ 3~ ~
~:~ ., ~ . . . . .
Product of Example 3 RATE OP
APPLICATION
(Lbs/Acre) 4 2 1 0.5 0025 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 Morning Glory 4 4 4 10 8 2 Yellow Foxtail 4 4 2 1 0 0 Barnyard Grass10 8 3 0 0 0 Johnson Grass 3 6 2 0 Q 0 Quack Grass - - 3 2 3 0 Wild Oa~s 5 . 7 7 0 0 0 Crabgrass 10 7 5 0 0 0 Sprangletop - - 9 1 O 0 Cheat Grass 3 0 0 8 0 O
Sugar Beet - - 10 10 10 10 Soybean - o 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 ~ o 2 . 0 0 0 Oats O O 7 o PRE-EMERGENCE HERBICIDE TEST DATA
Product of_Example 3 RATE OF
APPLICATION
(LbsJAcre) 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 Poxtail 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 g 0 0 Sugar Beet - - 10 10 10 10 Soybea~ - - 10 10 4 Cotton - - 10 10 10 10 Pinto Bea~ - - 10 8 7 0 Alfalfa - - 10 10 10 10 Whea~ . - - 10 10 3 Rice - - .10 0 0 0 Sorghum - - - 10 1 0 Corn - - 10 3 0 Oats - - 10 4 0 0 ~14-5~ ~
The herbicidal activi~y of the compounds of this invention was also demonstrated by.experiments carried ~ut for the post-emergence control of a variety of we~ds, In these experimen~s the compounds to be tested were fo~mula~ed as aqueous emulsions and sprayed at the indicated dosage on the foliage of the various weed species ~hat have attained prescribed size. After spraying, the plants were placed in a greenhouse and watered daily or more frequently. Water was not applied to. the foilage of the treated plants. The severity of the injury was determined 14 days after treat-ment and was rated on the scale of from 0 to 10 heretobefore described. The effectiveness of these compounds is de~on-strated by the following data:
POST-EMERGENCE HERBICIDE TEST DATA
.. _ . .. _ ,, .. w...... _ Pr ct of Exam 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 o 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 Cheat Grass 10 8 0 Sugar Beets 10 10 10 10 Cot~on 10 10 10 10 SoybeaDs lD 10 7 6 Pin~o Beans - 10 10 10 7 Alfalfa 10 10 10 10 Sorghum 10 3 0 0 Wheat 10 10 10 5 Rice 10 10 10 Corn 10 7 0 0 Oats 10 10 9 POST-EMERG~NCE HERBICIDE T.EST DATA
RATE OF
APPLICATION
~Lbs~Acre) 4 2 l 0.50.250.125 0.062 0.032 Yellow Nutsedge 10 7 .8 10 10 lO - -Wild Mus~ard 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 Glory10 10 10 10 10 10 0 0 Yellow Foxtail7 10 9 10 0 0 Barnyard Crass10 10 7 10 10 0 0 0 Johnson Grass10 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 l0 10 9 l 1 0 0 Pinto Beans - - 10 l0 10 . 0 ~ -Alfalfa - - 10 10 10 10 ~ - .
~. , .
f~
Sorghum - -10 1 O 0 o .
Whea~ 13 10 O 0 Ri ce - o0 O O 0 Corn - -10 1 1 0 - ~ , Oats - -10 5 0 0 - -.
.
7- ,
endothal, biuretl technical chlordanel dimethyl 2,3,5,6-tetrachloroterephthalate, diquat, erbon, DNC, DNBP, dichlorobenil, DPA, diphenamia, dipropalin, trifluraline, solan, dicryl, merphos, DMPAI DSMA, MSMh, potassium azide~
acrolein, benefin, bensulide, AMS, bromacil, 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine, 3,5-dione, bromoxynil, cacodylic acid, DMA, DPMF, cypromid, DCB, DCPA, dichlone, diphenatril, DMTT~ DNAP~ EBEPt EXD~
HCA, iosynil, IPX, isocril, potassium cyanate~ MAA, MAMA, MCPES, MCPP, MH, molinate, NPA, OC~I paraquat, PCPf picloram, DPA~ PCA, pyrichlor, sesone, terbac.il, 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 li~e.
.,~ _ ~ _ ~ mab/ ~
~$~
Such herbicides can also be used in the methods and composition of this invention in the form of their salts, esters, amides, and otheT derivatives whenever applicable to ~he par-ticular 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 ~ypes of weeds are known, including annuals such as pigweed9 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, dodder9 fumitory, groundsel~ hemp nettle, knowel, spurge, spurry, emex, jungle rice, pondweed, dog fennel, carpetweed, morning glory, bedstraw, ducksalad and naîad; 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 chick-weed, dandelion, campanula, field bindweed, Russian knapweed, mewquite, toadflax, yarrow, as~er, gromwell, horsetail, iron-weed, 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 ~his invention are particularly valuable for weed control because ~hey are toxic to many speci s and groups of weeds while they are relatively non~oxic ~o many beneficial plants. The exact amount of compound required will _g_ depend on a variety of factors, including the hardiness of the particular weed species, weather9 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 favorable conaitions.
The herbicidal toxicity of the new compounds of this invention can be illustrated by many of the es~ablished testing techniques known to the art, such as pre- and post emergence testing. ~
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 experi-ments small plastic greenhouse pots filled with dry soil were seeded with the various weed seeds. Twenty-four 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 so:Lutions containing emulsifiers were sprayed at the indicated concen~rations 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 frequently watering. The plants were main-tained under these conditions for a period of from 14 ~o 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, lp2 = slight injury, 3,4 = moderate injury3 556 = moderately severe injury~ 7,8,9 ~ seYere injury, and 10 = deathO The effectiveness of these compounds is demon stra~ed by the following data:
,_ ,. .
Produ_t of Ex mple 2 RATE OF
APPLICATION
~Lbs/Acre) 1 0.5 0.25 0.125 Wild Mustard 10 1 10 5 Bindweed 8 5 S 4 Pigweed 8 0 0 0 Velvet 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 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 0 0 0 Pinto Bean 0 0 0 0 Alfalfa 10 10 10 5 Wheat . 5 Rice 10 8 7 7 Sorghum 8 7 2 2 Corn 6 S 3 0 Oats 5 7 0 0 .. ~
Product of Example_2 -RATE OF
APPLICATION
(Lbs/Acre) 1 0.5 0.25 0.125 Wild Mustard 10 3 10 7 BiDdweed 10 O O 0 Pigweed 10 10 10 O
Velvet l.eaf 10 2 9 Morning Glory10 10 l0 7 Yellow Foxtail 10 O 0 0 Barnyard Grass l0 0 0 O
Johnson Grass 9 8 5 3 Quack Grass 5 8 0 0 Wild Oats lO 10 8 0 Crabgrass l0 10 8 O
Sprangletop 10 10 9 O
Cheat Grass 8 8 Sugar Beet 10 10 10 10 Soybean 10 3 2 0 Cot~on NE 0 O O
PintG Bean 9 10 0 O
Alfalfa 10 10 10 0 Wheat l0 lO 5 0 Rice 10 10 4 2 Sorghum 8 8 1 0 Corn 7 ~
9ats 10 10 1 O
-12~ , ~ 3~ ~
~:~ ., ~ . . . . .
Product of Example 3 RATE OP
APPLICATION
(Lbs/Acre) 4 2 1 0.5 0025 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 Morning Glory 4 4 4 10 8 2 Yellow Foxtail 4 4 2 1 0 0 Barnyard Grass10 8 3 0 0 0 Johnson Grass 3 6 2 0 Q 0 Quack Grass - - 3 2 3 0 Wild Oa~s 5 . 7 7 0 0 0 Crabgrass 10 7 5 0 0 0 Sprangletop - - 9 1 O 0 Cheat Grass 3 0 0 8 0 O
Sugar Beet - - 10 10 10 10 Soybean - o 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 ~ o 2 . 0 0 0 Oats O O 7 o PRE-EMERGENCE HERBICIDE TEST DATA
Product of_Example 3 RATE OF
APPLICATION
(LbsJAcre) 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 Poxtail 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 g 0 0 Sugar Beet - - 10 10 10 10 Soybea~ - - 10 10 4 Cotton - - 10 10 10 10 Pinto Bea~ - - 10 8 7 0 Alfalfa - - 10 10 10 10 Whea~ . - - 10 10 3 Rice - - .10 0 0 0 Sorghum - - - 10 1 0 Corn - - 10 3 0 Oats - - 10 4 0 0 ~14-5~ ~
The herbicidal activi~y of the compounds of this invention was also demonstrated by.experiments carried ~ut for the post-emergence control of a variety of we~ds, In these experimen~s the compounds to be tested were fo~mula~ed as aqueous emulsions and sprayed at the indicated dosage on the foliage of the various weed species ~hat have attained prescribed size. After spraying, the plants were placed in a greenhouse and watered daily or more frequently. Water was not applied to. the foilage of the treated plants. The severity of the injury was determined 14 days after treat-ment and was rated on the scale of from 0 to 10 heretobefore described. The effectiveness of these compounds is de~on-strated by the following data:
POST-EMERGENCE HERBICIDE TEST DATA
.. _ . .. _ ,, .. w...... _ Pr ct of Exam 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 o 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 Cheat Grass 10 8 0 Sugar Beets 10 10 10 10 Cot~on 10 10 10 10 SoybeaDs lD 10 7 6 Pin~o Beans - 10 10 10 7 Alfalfa 10 10 10 10 Sorghum 10 3 0 0 Wheat 10 10 10 5 Rice 10 10 10 Corn 10 7 0 0 Oats 10 10 9 POST-EMERG~NCE HERBICIDE T.EST DATA
RATE OF
APPLICATION
~Lbs~Acre) 4 2 l 0.50.250.125 0.062 0.032 Yellow Nutsedge 10 7 .8 10 10 lO - -Wild Mus~ard 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 Glory10 10 10 10 10 10 0 0 Yellow Foxtail7 10 9 10 0 0 Barnyard Crass10 10 7 10 10 0 0 0 Johnson Grass10 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 l0 10 9 l 1 0 0 Pinto Beans - - 10 l0 10 . 0 ~ -Alfalfa - - 10 10 10 10 ~ - .
~. , .
f~
Sorghum - -10 1 O 0 o .
Whea~ 13 10 O 0 Ri ce - o0 O O 0 Corn - -10 1 1 0 - ~ , Oats - -10 5 0 0 - -.
.
7- ,
Claims (5)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A compound with a general formula selected from:
and wherein m is zero or an integer of from one to 6;
n is zero or one; and R represents 1oweralkyl.
and wherein m is zero or an integer of from one to 6;
n is zero or one; and R represents 1oweralkyl.
2. A compound of general formula:
wherein m, n and R are as defined in claim 1.
wherein m, n and R are as defined 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 method of controlling weeds, comprising:
contacting said weeds with a herbicidal composition of a compound as defined in claim 1, 2 or 3.
contacting said weeds with a herbicidal composition of a compound as defined in claim 1, 2 or 3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38339182A | 1982-06-01 | 1982-06-01 | |
| US383,391 | 1989-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1189512A true CA1189512A (en) | 1985-06-25 |
Family
ID=23512920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000425522A Expired CA1189512A (en) | 1982-06-01 | 1983-04-08 | Urea compositions of matter |
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) | ES522736A0 (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 YU YU01175/83A patent/YU117583A/en unknown
- 1983-05-26 SE SE8302972A patent/SE8302972L/en not_active Application Discontinuation
- 1983-05-26 ES ES522736A patent/ES522736A0/en active Granted
- 1983-05-30 FR FR8308927A patent/FR2527607A1/en not_active Withdrawn
- 1983-05-30 BE BE0/210876A patent/BE896883A/en not_active IP Right Cessation
- 1983-05-30 GR GR71505A patent/GR78262B/el unknown
- 1983-05-30 DE DE19833319557 patent/DE3319557A1/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 RO RO83111130A patent/RO87127A/en unknown
- 1983-05-31 NO NO831952A patent/NO831952L/en unknown
- 1983-06-01 JP JP58097779A patent/JPS58219185A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2527607A1 (en) | 1983-12-02 |
| ZA832937B (en) | 1984-01-25 |
| NO831952L (en) | 1983-12-02 |
| KR840005136A (en) | 1984-11-03 |
| NZ203871A (en) | 1985-05-31 |
| DD211943A5 (en) | 1984-08-01 |
| YU117583A (en) | 1986-12-31 |
| AU555665B2 (en) | 1986-10-02 |
| JPS58219185A (en) | 1983-12-20 |
| GB2121034A (en) | 1983-12-14 |
| DK246383D0 (en) | 1983-05-31 |
| GB2121034B (en) | 1986-02-05 |
| RO87127B (en) | 1985-12-01 |
| RO87127A (en) | 1985-12-20 |
| DK246383A (en) | 1983-12-02 |
| PH19467A (en) | 1986-05-14 |
| CH654006A5 (en) | 1986-01-31 |
| BE896883A (en) | 1983-09-16 |
| ES8407044A1 (en) | 1984-09-01 |
| GR78262B (en) | 1984-09-26 |
| DE3319557A1 (en) | 1983-12-01 |
| GB8310916D0 (en) | 1983-05-25 |
| NL8301659A (en) | 1984-01-02 |
| KR860000849B1 (en) | 1986-07-09 |
| SU1209019A3 (en) | 1986-01-30 |
| SE8302972L (en) | 1983-12-02 |
| BR8302575A (en) | 1984-01-17 |
| IT1172261B (en) | 1987-06-18 |
| IT8348358A0 (en) | 1983-05-24 |
| AU1521783A (en) | 1984-01-19 |
| ES522736A0 (en) | 1984-09-01 |
| SE8302972D0 (en) | 1983-05-26 |
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