WO2007092184A2 - Method for improving harvestability of crops - Google Patents
Method for improving harvestability of crops Download PDFInfo
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- WO2007092184A2 WO2007092184A2 PCT/US2007/002267 US2007002267W WO2007092184A2 WO 2007092184 A2 WO2007092184 A2 WO 2007092184A2 US 2007002267 W US2007002267 W US 2007002267W WO 2007092184 A2 WO2007092184 A2 WO 2007092184A2
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- Prior art keywords
- compound
- alkyl
- amino
- regrowth
- cyclopropyl
- Prior art date
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- VQTVFIMEENGCJA-UHFFFAOYSA-N Cc1c(C)[nH]nc1 Chemical compound Cc1c(C)[nH]nc1 VQTVFIMEENGCJA-UHFFFAOYSA-N 0.000 description 1
- PUMREIFKTMLCAF-UHFFFAOYSA-N Cc1c[o]cn1 Chemical compound Cc1c[o]cn1 PUMREIFKTMLCAF-UHFFFAOYSA-N 0.000 description 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N Cc1n[nH]cc1 Chemical compound Cc1n[nH]cc1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Definitions
- This invention relates to a method for improving harvestability of cultivated plants by using certain pyrimidines and pyridines.
- Cultivated plants such as crops for food, feed, forage and fiber often benefit from treatment with certain chemicals to facilitate harvesting (i.e. improve harvestability) or to improve the quality of the harvested plant parts.
- Such chemical treatment before harvest is sometimes termed harvest conditioning, and the chemicals used are termed harvest aids.
- sugarcane is often treated with chemicals to inhibit growth, resulting in an increase in sucrose concentration.
- Tobacco can be treated with chemicals to induce ripening of the leaves so that more can be harvested at one time.
- Chemical treatments can be used to cause desiccation or abscission of foliage to prevent interference with mechanical harvesting when natural senescence is insufficient.
- potato plants are often chemically treated to desiccate haulms (i.e.
- This invention pertains to a method for inhibiting regrowth of foliage of a crop plant being conditioned for harvest or after harvest comprising applying to the plant foliage a regrowth-inhibiting effective amount of a compound of Formula 1, an jV-oxide or a salt thereof:
- R 1 is halogen; or C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C ⁇ cycloalkyl, C 2 -C 5 alkoxyalkyl, C 2 -C 6 alkylthioalkyl, each optionally substituted with 1-5 R 5 ; or a phenyl or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with 1 to 3 substituents independently selected from R 6 ;
- R2 is ((O) j C(Rl5)(Rl6 ))kR;
- R is CO 2 H or a regrowth-inhibiting effective derivative thereof
- R 3 is halogen, cyano, thiocyano, nitro, C 1 -Cs alkyl, C1-C5 haloalkyl, OR 7 , SR 8 or N(R 9 )R 10 ;
- W is H, -N(R 1 ⁇ R 12 , N 3 or -NO 2 ;
- X is N or CR 4 ;
- R 4 is H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, phenoxy, nitro, cyano or thiocyano; each R 5 is independently halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 - C 6 haloalkenyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 3 alkylthio Or C 1 -C 2 haloalkylthio; each R 6 is independently halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocyclo
- R 7 is H, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl or phenyl;
- R 8 is H, C 1 -C 4 alkyl or C 1 -C 3 haloalkyl
- R 9 and R 10 are independently H or C 1 -C 4 alkyl
- R 15 is H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, hydroxy, C 1 -C 4 alkoxy or C 2 -C 4 alkylcarbonyloxy;
- R 16 is H, halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; or R 15 and R 16 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; each R 30 is independently halogen, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio,
- each R 33 is independently H, C 1 -C 14 alkyl, C 1 -C 3 haloalkyl, C 1 -C 4 alkoxy, phenyl, phenoxy or benzyloxy; each R 40 is independently halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy,
- R 1 when R 1 is phenyl substituted by R 6 in the para position, said R 6 is other than t ⁇ rf-butyl, cyano or optionally substituted phenyl.
- this invention pertains to a harvest aid mixture for causing prolonged defoliation of a crop plant, such as cotton, being conditioned for harvest comprising a compound of Formula 1 and at least one compound acting as a defoliant or desiccant.
- This invention further relates to a method for inhibiting regrowth of foliage of a crop plant, such as cotton, comprising applying an effective amount of a compound of Formula 1 and at least one compound selected from compounds acting as a defoliant or desiccant.
- This invention also relates to an agricultural composition
- an agricultural composition comprising a compound of Formula 1 and at least one additional active ingredient selected from the group consisting of a herbicide or insecticide and at least one of a surfactant, and a solid or liquid diluent.
- compositions comprising, “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion.
- a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
- “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
- R 1 , R 12 , R 51 , R 57 , R 5S and R 61 refers to groups that are unsubstituted or have at least one non-hydrogen substituent.
- alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, /-propyl, or the different butyl, pentyl or hexyl isomers.
- Alkenyl includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.
- Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl.
- Alkynyl includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
- Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
- Alkoxy includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
- Alkoxyalkyl denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH3OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
- Alkenyloxy includes straight-chain or branched alkenyloxy moieties.
- alkynyloxy includes straight-chain or branched alkynyloxy moieties. Examples of “alkynyloxy” include HC ⁇ CCH 2 O, CH 3 C ⁇ CCH 2 O and CH 3 C ⁇ CCH 2 CH 2 O.
- Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
- Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
- -CH ⁇ O(CH 2 ) p r means
- Aromatic indicates that each of the ring atoms is essentially in the same plane and has a /j-orbital perpendicular to the ring plane, and in which (4n + 2) ⁇ electrons, when n is a positive integer, are associated with the ring to comply with H ⁇ ckel's rule.
- the terms "heteroaromatic ring” includes fully aromatic heterocycles.
- a wide variety of synthetic methods are known in the art to enable preparation of aromatic and nonaromatic heterocyclic rings and ring systems; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 and the twelve volume set of Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996.
- the heteroaromatic rings can be attached through any available carbon or nitrogen by replacement of a
- nitrogen-containing heterocycles can form /V-oxides since the nitrogen requires an available lone pair of electrons for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides.
- nitrogen-containing heterocycles which can form N-oxides.
- tertiary amines can form iV-oxides.
- Synthetic methods for the preparation of /V-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as f-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.
- MCPBA peroxy acids
- alkyl hydroperoxides such as f-butyl hydroperoxide
- sodium perborate sodium perborate
- dioxiranes such as dimethyldioxirane
- halogen either alone or in compound words such as “haloalkyl” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F 3 C, ClCH 2 , CF 3 CH 2 and CF 3 CCl 2 .
- haloalkenyl “haloalkynyl”, “haloalkoxy”, “haloalkylthio", and the like, are defined analogously to the term “haloalkyl".
- haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
- haloalkylthio examples include CCl 3 S, CF 3 S, CCl 3 CH 2 S and ClCH 2 CH 2 CH 2 S.
- C 2 alkoxyalkyl designates CH 3 OCH 2
- C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2
- C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
- all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
- a compound When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can vary, when the number of said substituents is greater than 1, said substituents are independently selected from the group of defined substituents.
- a group contains a substituent which can be hydrogen, for example W, R 4 , R 7 through R 12 , R 15 , R 16 , R 33 , R 51 , R 52 , R 55 through R5 9 and R 64 , then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
- Stereoisomers relating to the mixtures, compositions and methods of this invention can exist as one or more stereoisomers.
- the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
- one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
- the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
- the compounds of Formula 1 wherein R is CO 2 H are believed to be the compounds that bind to an active site on a plant enzyme or receptor causing inhibition of regrowth of the plant.
- R is CO 2 H
- Other compounds of Formula 1 wherein the substituent R is a group that can be transformed within plants or the environment to a carboxylic acid function (i.e. CO 2 H) provide similar regrowth-inhibiting effects and are within the scope of the present invention.
- regrowth-inhibiting effective derivative of the carboxylic acid when used to describe the substituent R in Formula 1 is defined as any salt, ester, carboxamide, acyl hydrazide, imidate, thioimidate, amidine, acyl halide, acyl cyanide, acid anhydride, ether, acetal, orthoester, carboxaldehyde, oxime, hydrazone, thioacid, thioester, dithiolester, nitrile or any other carboxylic acid derivative known in the art which does not extinguish the regrowth-inhibiting activity of the compound of Formula 1 and is or can be hydrolyzed, oxidized, reduced or otherwise metabolized in plants or soil to provide the carboxylic acid function, which depending upon pH, is in the dissociated or the undissociated form.
- Agriculturally suitable salts of the compounds relating to the mixtures, compositions and methods of the invention are salts formed by contact with acids or bases or through ion exchange such that the derived salts retain sufficient water solubility for bioavailability and thus regrowth-inhibiting efficacy and that the counterions of the salts are suitable for use in agriculture.
- the agriculturally suitable salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, rnaleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
- inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, rnaleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
- the agriculturally suitable salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, triethylamine or quaternary ammonium) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a carboxylic acid or phenol.
- organic bases e.g., pyridine, ammonia, triethylamine or quaternary ammonium
- inorganic bases e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium
- the present invention comprises compounds selected from Formula 1 and their /V-oxides and agriculturally suitable salts thereof.
- Particularly useful are regrowth-inhibiting effective derivatives of compounds of Formula 1 wherein R is CO2H formed with strong bases or amines.
- R is CO2H formed with strong bases or amines.
- contact of a carboxylic acid group (COjH) with a base causes deprotonation to give the corresponding carboxylate ion (CC> 2 ⁇ ) and a typically positively charged counterion derived from the base.
- the combination of the carboxylate ion and the counterion constitute a salt derivative of the carboxylic acid group.
- An extensive range of counterions form regrowth- inhibiting effective derivatives of compounds of Formula 1 wherein R is CO 2 H, as most of the derived salts have sufficient water solubility for bioavailability.
- alkali metal cation such as lithium, sodium or potassium
- quaternary ammonium such as tetramethylammonium
- ternary sulfonium such as trimethylsulfonium
- derived from an amine such as dimethylamine, diethanol amine (diolamine) or triethanolamine (trolamine).
- ester and thioester derivatives of CO ? H as R in the compounds of Formula 1 are also particularly useful.
- ester groups i.e. CO 2 R ⁇
- R ⁇ OH an alcohol
- R ⁇ is the radical derived from the alcohol
- thioester groups of formula C(O)SR AL may be conceptually viewed as the condensation product of a carboxylic acid function with a thioalcohol (often called a mercaptan) of formula R ⁇ SH; a variety of methods are known to prepare such thioesters.
- R is CO2H
- the compounds of Formula 1 wherein R is CO2H are effective regrowth inhibitors, and their derived esters and thioesters are susceptible to hydrolysis (to R being CO 2 H), particularly in the presence of hydrolytic enzymes
- the compounds of Formula 1 wherein R is an ester (i.e. CO 2 R AL ) or thioester (i.e. C(O)SR AL ) are generally useful as regrowth inhibitors.
- the ester and thioester derivatives, particularly ester derivatives are among the most conveniently prepared and useful.
- the radical RAL has more than one OH or SH function
- the radical may then be condensed with more than one pyrimidine or pyridine ring system of Formula 1 having CO 2 H as R.
- the derived multiply esterified derivatives can be hydrolyzed to the compound of Formula 1 having CO2H as R, said multiply esterified derivatives are among the regrowth-inhibiting effective derivatives of CO 2 H.
- R being CO 2 H is esterified with methanol, ethanol, propanol, isopropanol, f-butanol and phenol to form methyl, ethyl, propyl, /-propyl, r-butyl and phenyl esters, respectively.
- R being CO 2 H is esterified with methanol, ethanol, propanol, isopropanol, f-butanol and phenol to form methyl, ethyl, propyl, /-propyl, r-butyl and phenyl esters, respectively.
- foliage refers to leaves, stems, flowers, fruits and other parts of plants not covered by or immersed in the growing medium.
- foliar is an adjective and means of or relating to foliage.
- “Harvest conditioning” or “being conditioned for harvest” refers to the chemical treatment of crop plants prior to harvest to prepare them for harvest and to improve harvestability.
- the phrase “after harvest” refers to the period subsequent to gathering the harvestable portion of the crop and prior to preparing to plant the next crop.
- the term “harvestability” refers to the ability to rapidly and efficiently gather the harvestable portion of the crop while maintaining quality of the harvested portion, particularly using mechanical harvest devices.
- the term “harvest aid” refers to a chemical used advantageously to improve harvestability of cultivated plants, or increase quality of harvested plant parts, resulting, for example, in maximizing the collection of harvestable crop, achieving more efficient mechanical harvesting, or preserving high crop quality to provide maximum economic returns.
- Types of harvest aids include defoliant, desiccant, boll opener and regrowth inhibitor. It is well known that harvesting of certain crops may be aided by the use of substances that cause defoliation or desiccation of leaves thereby reducing the interference of leaves with harvesting personnel and machinery. For example, conditioning the cotton plant for harvest requires removal or desiccation of existing leaves and the prevention of the development of new leaves. Existing leaves are removed or conditioned either by defoliation or desiccation through the application of chemical products (harvest aids) as foliar sprays to the cotton plant. The defoliant and desiccant harvest aid products do not normally kill the cotton plant, but only result in the removal of existing leaves.
- Defoliation is the shedding of plant leaves, which ordinarily occurs when the leaves become senescent. Leaf shedding (abscission) results from activity of special cells at the base of the leaf petiole where it joins the stem.
- the “state of defoliation” refers to the condition of a plant that has shed its leaves.
- a “defoliant” is a chemical compound that either impacts plant hormonal activity related to leaf loss or causes direct injury to leaves, both at a level that promotes leaf drop (abscission). The activity of a defoliant typically varies by molecular structure and environmental conditions, but defoliants generally require days or weeks to remove leaves from the plants by causing leaves to abscise completely from the plant.
- Desiccation is drying of plant tissues that can be caused by disruption of cell membranes and rapid loss of moisture.
- a “desiccant” refers to a contact-type herbicide that destroys cell membranes leading to rapid moisture loss and leaf desiccation, typically killing leaves rapidly with limited abscission.
- Desiccants produce quick injury that is more severe than that seen with defoliants, causing leaf dehydration and death within one to several days.
- Desiccants are often applied as a follow-up treatment after application of defoliants. Both desiccation and defoliation result in the absence of green leaves on a plant that is being conditioned for harvest.
- Prolonged defoliation is the extension of duration of a state of defoliation (or absence of green leaves) beyond that accomplished by applying a defoliant or desiccant.
- a "boll opener” refers to a chemical compound that accelerates opening of mature bolls of cotton plants.
- Regrowth is a term given to new leaves and stems produced by a plant after defoliation or desiccation.
- a “regrowth inhibitor” is a chemical compound applied to plants primarily to inhibit leaf and stem growth (regrowth) or to enhance or extend the state of defoliation resulting from the application of defoliants or desiccants. It is understood that when a regrowth inhibitor is applied concurrently or subsequently with a defoliant or desiccant, it results in extending the period without green leaves (state of defoliation), i.e. prolonged defoliation.
- Cotton is a deciduous perennial plant.
- cotton culture as practiced in all major growing areas, involves the management of this perennial plant as an annual crop.
- cotton As it is grown in commercial lint (fiber) and seed production worldwide, cotton has been selected and bred and is managed to exhibit a determinant nature to the extent that it is grown as an annual.
- the cotton plant is managed for its ability to go through a reproductive phase within one growing season with no commercial interest in its perennial nature.
- artificial means i.e. harvest aid chemicals, are used to prepare the plant for optimum harvestability.
- Terminal regrowth is the continuation or resumption of new growth in the growing point in the plant apex (apical meristem). Terminal regrowth frequently occurs following application of defoliants, desiccants and boll opening materials in preparation for cotton harvest. When foliage and immature fruit forms are removed from physiologically mature cotton plants under conditions of available moisture, fertility, and heat, the cotton plant often responds by initiating terminal regrowth. Terminal regrowth is a source of lint stain and foreign material during harvest, a source of excess moisture which limits seed cotton storage, provides sites for insect development, reduces harvest efficiency, and, finally, is aesthetically very objectionable. Harvest aids containing thidiazuron or combinations of thidiazuron and diuron are frequently used to limit terminal regrowth, with varying degrees of success.
- Basal regrowth occurs when dormant axillary buds, primarily at main-stem nodes, germinate, usually following application of cotton harvest aids such as desiccants, defoliants and boll openers. Basal regrowth may occur in concert with terminal regrowth following any harvest aid application; however, it is most common following application of ethephon and ethephon/cyclanilide combinations for boll opening. These harvest aid materials appear to interfere with apical dominance in the cotton plant and under favorable conditions greatly increase the occurrence of basal regrowth. Basal regrowth causes all of the problems associated with terminal regrowth and potentially interferes with harvest efficiency to a greater extent than terminal regrowth.
- Basal regrowth tends to lag behind terminal regrowth initially; however, because it originates from many sites, it has the capacity to produce great amounts of foliage and/or reproductive forms relatively quickly.
- Regrowth inhibitors particularly effective on basal regrowth are few. Thidiazuron and thidiazuron/diuron combinations limit basal regrowth less effectively and less consistently than terminal regrowth.
- basal regrowth In addition to conditioning the cotton plant for harvest, preventing the continuation or resumption of emergence of new leaves and stems (regrowth) after harvest is also important. Basal regrowth following harvest, or harvest followed by mowing, is a problem in much of the cotton belt in the southern U.S. At the lowest latitudes, basal regrowth will continue indefinitely, wasting soil fertility and moisture, and providing sites for regeneration of the boll weevil and other cotton insect pests. Establishment of a host-free period is a key insect management technique in many areas and requires maintaining the field free from live cotton plants for a period of several months after harvest. In more temperate environments, basal regrowth persists only until the first freeze. However, this period may extend for 3Q-90 days after harvest.
- the present invention is effective for preventing regrowth when applied to a crop being conditioned for harvest or after harvest.
- the present invention has been found to be effective for preventing any kind of regrowth including basal and terminal regrowth.
- Transgenic cotton refers to cotton varieties that have been genetically modified to incorporate genes for useful traits from other species.
- transgenic cotton may incorporate genes for producing insecticidal proteins or herbicide tolerance.
- the cotton of the present invention includes transgenic cotton.
- Embodiment Al The method as set forth in the Summary of the Invention wherein in the compound of Formula 1
- R2 is ((O) j C(Rl5)(Rl6 ))kR;
- R 51 is H or a radical selected from C 1 -Ci 4 alkyl, C 3 -C 12 cycloalkyl, C 4 -C 12 alkylcycloalkyl, C 4 -C 12 cycloalkylalkyl, C 2 -C 14 alkoxyalkyl, C 3 ⁇ -C 14 alkoxyalkoxyalky], C 2 -C 14 hydroxyalkyl, C 2 -C 14 alkenyl, C 2 -C 14 alkynyl, benzyl and phenyl, each radical optionally substituted with 1-3 R 61 ; or R 51 is a divalent radical linking the carboxylic ester function CO 2 R 51 of each of two pyrimidine ring systems of Formula 1, the divalent radical selected from
- R 52 is H, C)-C 10 aI M optionally substituted with 1-3 R 62 , or benzyl;
- R 53 and R 54 are independently C 1 -C 4 alky] or C 1 -C 3 haloalkyl; or
- R 53 and R5 4 are taken together as -CH 2 CH 2 -, -CH 2 CH(CH 3 )- or -(CH 2 ) 3 -;
- R 55 is H, C 1 -C 4 alkyl, hydroxy or C 1 -C 4 alkoxy;
- R 56 is H or C 1 -C 4 alkyl;
- R 57 and R 5 ⁇ are H; or a radical selected from C 1 -C ]4 alkyl, C 3 -C 12 cycloalkyl,
- Y is O, S or NR6 4 ;
- RS9 is H, C 1 -C 3 alky), C 1 -C 3 haloalkyl, C 2 -C 4 alkoxyalkyl, OH Or C 1 -C 3 alkoxy;
- R 60 is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 2 -C 4 alkoxyalkyl; or R 5 9 and R 60 are taken together as -(CH 2 V.
- each R 61 is independently halogen, cyano, hydroxycarbonyl, C 2 -C 4 alkoxycarbonyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 8 alkoxyalkoxy, C ⁇ -C ⁇ .
- each R 62 is independently halogen, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio,
- each R 63 is independently halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, hydroxy, C 1 -C 4 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 3 alkylamino, C 2 -C 4 dialkylamino or nitro;
- R 64 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 2 -C 4 alkoxyalkyl; and p is an integer from 1 to 4.
- Embodiment A2 The method of Embodiment Al wherein R 2 is OCH 2 CO 2 R 5 1 .
- Embodiment A3. The method of Embodiment Al wherein R 2 is CO 2 R 51 , CH 2 OR 52 ,
- Embodiment A4 The method of Embodiment A3 wherein R 2 is CO 2 R 51 .
- Embodiment A5. The method of Embodiments A4 wherein R 51 is H, C 1 -C 1 Q alkyl, C 2 -
- Embodiment A6 The method of Embodiment A5 wherein R 51 is H, C 1 -C 4 alkyl, C 2 -
- Embodiment A7 The method of Embodiment A6 wherein R 5 * is H or C 1 -C 2 alkyl.
- Embodiment A8 The method of Embodiment A5 wherein R 51 is 05-C 1Q alkyl, C 5 -C 1Q alkoxyalkyl, C5-CJ0 alkoxyalkoxyalkyl or Cs-C 1 Q hydroxyalkyl.
- Embodiment A8 wherein R 51 is C5-C8 alkyl, C5-C8 alkoxyalkyl, C 5 -Cg alkoxyalkoxyalkyl Or C 5 -Cs hydroxyalkyl.
- Embodiment AlO The method of Embodiment A3 wherein R 2 is COoH or a salt thereof.
- Embodiment All The method of Embodiment AlO wherein R 2 is CO 2 H salt derivative.
- Embodiment A12 The method of Embodiment Al wherein R 2 is CO 2 H, a regrowth- inhibiting effective salt or an ester or thioester derivative thereof.
- Embodiment A13 The method of Embodiment A12 wherein R 2 is CO 2 H, a regrowth- inhibiting effective salt or an ester derivative thereof.
- Embodiment A 14 The method as set forth in the Summary of the Invention wherein in the compound of Formula 1 R 1 is halogen; or cyclopropyl or isopropyl, each optionally substituted with 1-2 R 5 .
- Embodiment A15 The method as set forth in the Summary of the Invention wherein in the compound of Formula 1 R 1 is a phenyl or 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 3 substituents independently selected from R 6 .
- Embodiment A16 A compound of Embodiment A15 wherein R 1 is one of U-I through U-50 depicted in Exhibit 1;
- Embodiment A17 The method of Embodiment A14 wherein R 1 is cyclopropyl optionally substituted with 1-2 R 5 .
- Embodiment A18 The method of Embodiment A14 wherein R 1 is isopropyl optionally substituted with 1-2 R 5 .
- Embodiment A19 The method of Embodiment A14 wherein R 1 is phenyl optionally substituted with 1-3 R 6 .
- Embodiment A20 The method of Embodiment A14 wherein R 1 is halogen. Embodiment A21. The method of Embodiment A20 wherein R 1 is Cl. Embodiment A22. The method of Embodiment A17 wherein R 1 is cyclopropyl. Embodiment A23. The method of Embodiment A19 wherein R 1 is phenyl substituted with a R 6 radical in the para position and optionally with 1-2 R 6 in other positions. Embodiment A24. The method of Embodiment A23 wherein R 1 is phenyl substituted with a halogen, methyl or methoxy radical in the para position and optionally with 1-2 radicals selected from halogen and methyl in other positions.
- Embodiment A25 The method of Embodiment A24 wherein R 1 is phenyl substituted with a halogen radical in the para position and optionally with 1-2 radicals selected from halogen and methyl in other positions.
- Embodiment A26 The method of Embodiment A25 wherein R 1 is phenyl substituted with a Br or Cl radical in the para position and optionally with 1-2 radicals selected from halogen and methyl in other positions.
- Embodiment A27 The method of Embodiment A26 wherein R 1 is phenyl substituted with a Br or Cl radical in the para position.
- Embodiment A28 The method as set forth in the Summary of the Invention wherein in the compound of Formula 1 R 3 is F, Cl or Br.
- Embodiment A29 The method of Embodiment A26 wherein R 3 is Cl.
- Embodiment A30 The method as set forth in the Summary of the Invention wherein in the compound of Formula 1 X is N.
- Embodiment A31 The method as set forth in the Summary of the Invention wherein in the compound of Formula 1 X is CR 4 .
- Embodiment A32 The method of Embodiment A31 wherein R 4 is H, F, Cl or Br. Embodiment A33. The method of Embodiment A32 wherein R 4 is H, F or Cl. Embodiment A34. The method of Embodiment A33 wherein R 4 is H or Cl. Embodiment A35. The method of Embodiment A34 wherein R 4 is H. Embodiment A36. The method as set forth in the Summary of the Invention wherein in the compound of Formula 1 W is H or -N(Rl l)Rl2. Embodiment A37. The method of Embodiment A36 wherein W is H. Embodiment A38. The method of Embodiment A36 wherein W is NH2-
- Embodiment Bl The method as set forth in the Summary of the Invention comprising a compound of Formula 1 is applied with at least one compound selected from compounds acting as a defoliant or desiccant.
- Embodiment B2 The method as set forth in Embodiment Bl wherein the at least one defoliant or desiccant compound is selected from the group consisting of tribufos (S ⁇ S-tributylphosphorotrithioate), dimethipin, thidiazuron, diuron, carfentrazone-ethyl, pyraflufen, ethephon, cyclanilide, AMADS (1-aminomethanamide dihydrogen tetraoxosulfate), sodium chlorate, paraquat, glyphosate, e ⁇ dothal, cacodylic acid, urea phosphate and their agriculturally suitable salts.
- tribufos S ⁇ S-tributylphosphorotrithioate
- dimethipin dimethipin
- thidiazuron diuron
- carfentrazone-ethyl pyraflufen
- ethephon cyclanilide
- AMADS (1-aminome
- Embodiment B3 The method as set forth in Embodiment B2 wherein the at least one defoliant or desiccant compound is selected from the group consisting of tribufos, thidiazuron, ethephon, cyclanilide, AMADS, sodium chlorate, cacodylic acid, urea phosphate and their agriculturally suitable salts.
- Embodiment B4 The method as set forth in Embodiment B3 wherein for causing prolonged defoliation of a cotton plant being conditioned for harvest comprising a compound of Formula 1 and at least one compound selected from the group consisting of tribufos, thidiazuron, ethephon, cyclanilide, AMADS, sodium chlorate, cacodylic acid, urea phosphate and their agriculturally suitable salts.
- Embodiment B5. The method as set forth in Embodiment B2 wherein the component is tribufos.
- Embodiment B6 The method as set forth in Embodiment B2 wherein the component is thidiazuron.
- Embodiment B7 The method as set forth in Embodiment B2 wherein the component is a mixture of thidiazuron and diuron.
- Embodiment B8 The method as set forth in Embodiment B2 wherein the component is a mixture of thidiazuron and dimethipin.
- Embodiment B9 The method as set forth in Embodiment B2 wherein the component is ethephon.
- Embodiment BlO The method as set forth in Embodiment B2 wherein the component is a mixture of ethephon and cyclanilide.
- Embodiment Bl 1. The method as set forth in Embodiment B2 wherein the component is a mixture of ethephon and AMADS.
- Embodiment B 12 The method as set forth in Embodiment B2 wherein the component is sodium chlorate.
- Embodiment B 13 The method as set forth in Embodiment B2 wherein the component is cacodylic acid.
- Embodiment B 14 The method as set forth in Embodiment B2 wherein the component is a mixture of sodium cacodylate and cacodylic acid.
- Embodiment B 15. The method as set forth in Embodiment B2 wherein the component is a mixture of ethephon and urea phosphate.
- Embodiment B16 The method as set forth in Embodiment B2 wherein the component is sodium chlorate.
- Embodiment B 13 The method as set forth in Embodiment B2 wherein the component is cacodylic acid.
- Embodiment B 14 The method as set forth in Embodiment B2 wherein the component is a mixture of sodium cacodylate and cacodylic acid.
- Embodiment B 15 The method as set forth
- a mixture comprising a compound of Formula 1 and a component consisting of at least one compound or mixture selected from the group consisting of tribufos, thidiazuron, ethephon, cyclanilide, AMADS, sodium chlorate, cacodylic acid, urea phosphate and their agriculturally suitable salts.
- Embodiment B 17 The method as set forth in any one of Embodiments B2-B16 wherein the compound of Formula 1 and the component consisting of at least one compound or mixture selected from the group of Embodiment B2 are in a weight ratio in the range of about 1:500 to 100: 1.
- Embodiment BlS The method of Embodiment B 17 wherein the compound of Formula
- Embodiment B 19 The method of Embodiment B 18 wherein the compound of Formula
- Embodiment B20 The method as set forth in the Summary of the Invention for inhibiting regrowth in a crop plant wherein the compound is applied to a crop plant being conditioned for harvest.
- Embodiment B21 The method of Embodiment B20 for inhibiting regrowth in a cotton plant wherein the compound is applied to a cotton plant being conditioned for harvest.
- Embodiment B22 The method of Embodiment B21 wherein the regrowth being inhibited is basal regrowth.
- Embodiment B23 The method of Embodiment B21 wherein the regrowth being inhibited is terminal regrowth.
- Embodiment B24 The method as set forth in the Summary of the Invention for inhibiting regrowth in a crop plant wherein the compound is applied to a crop plant being conditioned for harvest.
- Embodiment B21 The method of Embodiment B20 for inhibiting regrowth in a cotton plant wherein the compound is applied to a cotton plant being conditioned for harvest.
- Embodiment B25 The method as set forth in the Summary of the Invention for inhibiting regrowth in a cotton plant wherein the compound is applied after harvest.
- Embodiment B26 The method Embodiment B25 wherein the regrowth being inhibited is basal regrowth.
- Embodiment B27 The method Embodiment B25 wherein the regrowth being inhibited is terminal regrowth.
- Embodiment Cl The method as set forth in the Summary of the Invention wherein the crop plant is selected from cotton, tuberous crops such as potato, beets and the like, citrus tree, tomato, pepper, tobacco, peanut and sugarcane.
- Embodiment C2 The method of Embodiment Cl wherein the crop plant is cotton.
- Embodiment A The method as set forth in the Summary of the Invention or in
- Embodiment Al wherein in the compound of Formula 1 R 1 is halogen; or C 1 -C 3 alkyl or C 3 -C 5 cycloalkyl, each optionally substituted with
- R 5 1—2 R 5 ; or a phenyl or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with 1 to 3 substituents independently selected from R 6 ; R 3 is halogen; W is H or NH 2 ; and R 4 is H or halogen.
- Embodiment B The method of Embodiment A wherein R 1 is C 3 --C 5 cycloalkyl optionally substituted with 1-2 R 5 , or phenyl or 5- or 6- membered heteroaromatic ring, each ring optionally substituted with 1 to 3 substituents independently selected from R 6 ;
- X is N;
- each R 5 is independently halogen, C 1 -C 6 alkyl or C 1 -C ⁇ haloalkyl; and each R 6 is independently halogen, cyano, nitro, C 1 -C4 alkyl, C 1 -C4 haloalkyl Or C 1 -
- Embodiment C The method of Embodiment B wherein R 1 is cyclopropyl or phenyl substituted with a halogen, methyl or methoxy radical in the para position and optionally with 1-2 radicals selected from halogen and methyl in other positions.
- Embodiment D The method of Embodiment B wherein R 2 is CO 2 H or a salt thereof; or R 2 is CO 2 R 51 ; and R 51 is benzyl, C 1 -C 10 alkyl, C 2 -C 10 alkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl or C 2 -
- Embodiment E The method of Embodiment D wherein R 1 is cyclopropyl, 4-Br-phenyl or 4-Cl-phenyl; R 2 is CO 2 H or a salt thereof; or R 2 is CO 2 R 51 ; and R 51 is C 1 -C 2 alkyl.
- Embodiment F The method of Embodiment D wherein R 1 is cyclopropyl, 4-Br-phenyl or 4-Cl-phenyl; R 2 is CO 2 R 51 ; and
- R 51 is C 5 -C 8 alkyl, C 5 -C 8 alkoxyalkyl, C 5 -C 8 alkoxyalkoxyalkyl or C 5 -C 8 hydroxyalkyl.
- Embodiments include the method as set forth in the Summary of the Invention wherein the compound of Formula 1 is selected from the group consisting of: methyl ⁇ -amino-S-bromo-Z-cyclopropyl- ⁇ pyrirnidinecarboxylate (Compound 1), ethyl 6-amino-5-bromo-2-cycIopropyl-4-pyrimidinecarboxylate (Compound 2),
- Compounds of Formula 1 can be prepared by one or more of the methods and variations thereof as described in PCT Patent Publication WO 2005/063721, U.S. Patent Publication 2004/0198608 or U.S. Patent 6,784,137, which are hereby incorporated by reference in their entirety.
- compounds 2, 4, 8, 9 and 14 as identified in Table 1 can be prepared by the methods described in Example 1 (page 27), Example 3 (page 31), Example 5 (page 33), Example 4 (page 32), and Example 2 (page 29), respectively, of PCT Publication WO 2005/063721.
- Compound 15 is commercially available from Agripha or Dow AgroSciences.
- Compound 16 is commercially available from Agripha.
- Compound 29 can be prepared by the method described in Example 1 (Column number 9) of U.S. Patent 6,297,197, which is hereby incorporated by reference in its entirety.
- Compound 30 is commercially available from Dow AgroSciences.
- the harvest aid compounds acting as a defoliant or desiccant have been described in published patents and scientific journal papers. Many of these compounds are commercially available as active ingredients in harvest aid products. These compounds are described in compendia such as The Pesticide Manual, 13th edition, C. D. S. Thomlin (Ed.), British Crop Protection Council, Surrey, UK, 2003.
- the present invention is used advantageously to improve harvestability of cultivated plants, which results in a higher economic (crop) yield.
- the efficacy for improving harvestability of cultivated plants depends on, among other things, the amount of the compound of Formula 1 applied per hectare (or acre), the treatment time, and the type of plant to which it is applied.
- the compound of Formula 1 is mixed together with one or more defoliants or desiccants (i.e.
- the efficacy for improving harvestability of cultivated plants also depends on, among other things, the amount of the combination of a compound of Formula 1 and the component acting as a defoliant or desiccant, applied per hectare (or acre), and the relative proportions of the component acting as a defoliant or desiccant to the compound of Formula 1.
- the desired harvest aid effects of regrowth inhibition, defoliation or desiccation, as well as boll opening it is typical to use multiple products in mixture or sequence.
- the principal contribution to harvestability from applying a compound of Formula 1 alone or in combination or in sequence with defoliants, desiccants or boll openers is prevention of basal as well as terminal regrowth.
- defoliant, desiccant or boll opener in combination or in sequence with a compound of Formula 1 typically does not reduce the effectiveness of the compound of Formula 1 in preventing regrowth.
- the effect of mixing a compound of Formula 1 with defoliants, desiccants or boll openers on defoliation, desiccation or boll opening may depend on factors such as application timing, and in certain situations an enhancement of defoliation, desiccation or boll opening may be apparent.
- the defoliation, desiccation and/or regrowth inhibition effects exhibited by the combination of a compound of Formula 1 and at least one compound acting as a defoliant or desiccant may be significantly better than those observed when a compound of Formula 1 is employed alone.
- the present invention is useful for regrowth inhibition on crop plants whose harvestability is improved by defoliation and/or desiccation.
- crops include but are not limited to, cotton, tuberous crops such as potato, beets and the like, citrus tree, tomato, pepper, tobacco, peanut and sugarcane.
- Cotton is an example of a crop where the use of the regrowth inhibitors according to the present invention is particularly valuable.
- Useful formulations employed in the present invention can be prepared in conventional ways.
- Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels.
- Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible (“wettable”) or water-soluble.
- Active ingredient(s) can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated")- Encapsulation can control or delay release of the active ingredient(s).
- Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare.
- High-strength compositions are primarily used as intermediates for further formulation.
- the formulations will typically contain effective amounts of active ingredient(s), diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
- High Strength Compositions 90-99 0-10 0-2 Typical solid diluents are described in Watkins et a]., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses " . All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
- Typical surfactants which may be utilized include calcium lignin sulfonate, polyoxyethyleneoctylphenol ethers and naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates, and substituted benzenesulfonic acids and their salts.
- Particularly useful in formulations employed in the present invention are surfactants (i.e. surface-active compounds) having one or more phosphate groups that are partially (not fully) esterified and in which the esterified acid radicals are esterified with compounds selected from the following group of alcohol components:
- alkanols having, for example, 1 to 22 carbon atoms, preferably 1 to 12 carbon atoms, in particular from 4 to 12 or 4 to 8 carbon atoms, or unsubstituted or substituted cycloalkanols having preferably 5 to 12 carbon atoms, e.g. cyclohexanol, alkylcyclohexanols, cyclopentanol;
- oxyalkylated alkanols having up to 24 carbon atoms in the alkyl radical and 1 to 150 alkyleneoxy units in the alkyleneoxy or polyalkyleneoxy moiety, preferably those having 4 to 22 carbon atoms, in particular 10 to 20 carbon atoms in the alkyl radical and 1 to 60, in particular 3 to 30 alkyleneoxy units in the alkyleneoxy or polyalkyleneoxy moiety;
- phenol or oxyalkylated phenol where the phenyl radical is in each case unsubstituted or substituted by 1 to 3 alkyl radicals having preferably in each case 4 to 12 carbon atoms or by 1 to 3 aryl or arylalkyl radicals having 6 to 12 carbon atoms, and having, in the oxyalkylated case, 1 to 150 alkyleneoxy units in the alkyleneoxy or polyalkyleneoxy moiety, preferably oxyalkylated phenol having 1 to 20 alkyleneoxy units or oxyalkylated phenol which is substituted by 1 to 3 alkyl radicals having in each case 4 to 12 carbon atoms and has 1 to 60, in particular 4 to 30, alkyleneoxy units, or oxyalkylated phenol which is substituted by 1 to 3 aryl or arylalkyl radicals having 6 to 12 carbon atoms and has 1 to 100, in particular 10 to 30, alkyleneoxy units; and (d) oxyalkylated alkyl
- Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
- Liquid diluents include, for example, water, iV ⁇ /V-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, propylene carbonate, dibasic esters, paraffins, alkylbenzenes, alkylnaphthalenes, glycerine, triacetine, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as hexyl acetate, heptyl acetate and octyl acetate, and alcohols such as methanol, cyclohexanol, decanol, benzyl and tetrahydr
- Useful formulations of this invention may also contain materials well known to those skilled in the art as formulation aids such as antifoams, film formers and dyes.
- Antifoams can include water dispersible liquids comprising polyorganosiloxanes like Rhodorsil® 416.
- the film formers can include polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes.
- Dyes can include water dispersible liquid colorant compositions like Pro-lzed® Colorant Red.
- formulation aids include those listed herein and those listed in McCutcheon's 2001, Volume 2: Functional Materials published by MC Publishing Company and PCT Publication WO 03/024222.
- While a compound of Formula 1 can be used alone to inhibit regrowth in plants, it generally is applied to plants in conjunction with other substances, such as, carrier vehicles, wetting agents, emulsifiers, and solvents.
- exemplary carrier vehicles include water, aliphatic or aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone and mineral or vegetable oil fractions.
- the particularly preferred carrier vehicle is water, based on its availability and cost.
- Solutions can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S.
- Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
- T. S. Woods "The Formulator's Toolbox - Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R.
- the optimal time to apply the compounds of Formula 1 to cotton being conditioned for harvest, with or without other harvest aids selected from defoliants or desiccants, is mainly based on the maturity of cotton bolls and/or the percent of cotton bolls that are open or unopen, though weather and plant conditions can also be factors. Defoliation that occurs too early may result in lower yield and quality. Defoliation that occurs too late may increase the chance of boll rot and may be less effective as a result of lower temperatures.
- the harvest aids of the present invention are preferably applied to cotton fields at the time when 5 % to 95 % of cotton bolls have opened.
- the compound of Formula 1 is applied to the foliage of the crop plant at about 0.0001 to 20 kilograms per hectare (kg/ha) with a preferred range of about 0.001 to 5 kg/ha and a more preferred range of about 0.004 to 3 kg/ha.
- a preferred range of about 0.001 to 5 kg/ha and a more preferred range of about 0.004 to 3 kg/ha is applied to the foliage of the crop plant at about 0.0001 to 20 kilograms per hectare (kg/ha) with a preferred range of about 0.001 to 5 kg/ha and a more preferred range of about 0.004 to 3 kg/ha.
- the combined concentrations of the compounds of Formula 1 and at least one compound selected from compounds acting as defoliants or desiccants in the composition of the present invention is generally at least about 25 wt. %, preferably at least about 40 wt. %, and more preferably at least about 50 wt. % based upon the total weight of the composition.
- the composition is typically diluted to contain from about 1 to about 80 wt. % of the active agents, about 20 to about 99 wt. % of a solid or liquid carrier vehicle, and optionally up to about 20 wt. % of a surface-active substance.
- the ratio of the weight of the compound of Formula 1 to the weight of the component acting as a defoliant or desiccant is typically about 1:500 to about 100:1. Another effective weight ratio is about 1:500 to about 40:1 or about 1:100 to about 1: 1.
- the general and preferred ranges for the ratio of the moles of the compound of Formula 1 to the moles of the compound acting as a defoliant or desiccant are comparable to the above weight ratio ranges. The optimum ratios can be easily determined by those skilled in the art based on the combination of harvest aid activities desired.
- the mixture of the present invention has been found to be highly effective for defoliation or desiccation and regrowth inhibition of plants, such as cotton, when the amount of the composition of the active ingredients in this present invention applied is at least about 0.005, preferably about 0.005 to about 12.5, and more preferably about h to about 9.5 kilograms per hectare (kg/ha).
- the use rates of the combination of the present invention that are effective as harvest aids can be determined through typical testing.
- composition of the present invention When the composition of the present invention is sprayed from the ground, it is generally diluted with a carrier vehicle (for example, water) to provide a spray volume from about 9 to about 2,000 liters per hectare (L/ha). Preferably, a spray volume of about 47 to about 500 L/ha is utilized. In the case of aerial spraying, a more concentrated solution is commonly used and typically applied at a rate of about 18 to about 140, and preferably about 19 to about 95 L/ha.
- a carrier vehicle for example, water
- compounds of Formula 1 can be used alone or in combination with herbicides, insecticides and fungicides, and other agricultural chemicals such as fertilizers.
- herbicides with which compounds of this invention can " be formulated are: bromoxynil, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron, clethodim, diflufenzopyr, diuron, fenoxaprop-ethyl, fluazifop-P-butyl, fluometuron, glyphosate and its salts such as ammonium, isopropyl ammonium and trimesium, lactofen, linuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium
- a compound of Formula 1 is combined or used with at least one defoliant or desiccant compound selected from the group consisting of tribufos (S ⁇ .S-tributylphosphorotrithioate), dimethipin, thidiazuron, diuron, carfentrazone-ethyl, pyraflufen, ethephon, cyclanilide, AMADS (1-aminomethanamide dihydrogen tetraoxosulfate), sodium chlorate, paraquat, glyphosate, endothal, cacodylic acid, urea phosphate and their agriculturally suitable salts.
- tribufos S ⁇ .S-tributylphosphorotrithioate
- dimethipin dimethipin
- thidiazuron diuron
- carfentrazone-ethyl pyraflufen
- ethephon cyclanilide
- AMADS 1-aminomethanamide dihydrogen tetraoxos
- a mixture comprising a compound of Formula 1 and a component consisting of at least one compound or mixture selected from the group consisting of tribufos, thidiazuron, ethephon, cyclanilide, AMADS, sodium chlorate, cacodylic acid, urea phosphate and their agriculturally suitable salts.
- tribufos thidiazuron
- ethephon cyclanilide
- AMADS sodium chlorate
- cacodylic acid urea phosphate
- urea phosphate and their agriculturally suitable salts.
- Specifically preferred mixtures are selected from the group consisting of: the combinations of Compound 1, Compound 2, Compound 3, Compound 4, Compound 5, Compound 6, Compound 7, Compound S, Compound 9, Compound 10, Compound 11, Compound 12, Compound 13, Compound 14, Compound 15, Compound 16, Compound 17, Compound 18, Compound 19, Compound 20, Compound 21, Compound 22, Compound 23, Compound 24, Compound 25 or Compound 26 with tribufos, the combinations of Compound 1, Compound 2, Compound 3, Compound 4, Compound 5, Compound 6, Compound 7, Compound 8, Compound 9, Compound 10, Compound 11, Compound 12, Compound 13, Compound 14, Compound 15, Compound 16, Compound 17, Compound 18, Compound 19, Compound 20, Compound 21, Compound 22, Compound 23, Compound 24, Compound 25 or Compound 26 with dimethipin, the combinations of Compound 1, Compound 2, Compound 3, Compound 4, Compound 5, Compound 6, Compound 7, Compound 8, Compound 9, Compound 10, Compound 11, Compound 12, Compound 23, Compound 24, Compound 25 or Compound 26 with dimethipin, the combinations of Com
- Also specifically preferred mixtures are selected from the group consisting of: the combinations of Compound 27, Compound 28, Compound 29 or Compound 30 with tribufos, the combinations of Compound 27, Compound 28, Compound 29 or Compound 30 with dimethipin, the combinations of Compound 27, Compound 28, Compound 29 or Compound 30 with thidiazuron, the combinations of Compound 27, Compound 28, Compound 29 or Compound 30 with a mixture of thidiazuron and diuron, the combinations of Compound 27, Compound 28, Compound 29 or Compound 30 with a mixture of thidiazuron and dimethipin, the combinations of Compound 27, Compound 28, Compound 29 or Compound 30 with carfentrazone-ethyl, the combinations of Compound 27, Compound 28, Compound 29 or Compound 30 with pyraflufen, the combinations of Compound 27, Compound 28, Compound 29 or Compound 30 with ethephon, the combinations of Compound 27, Compound 28, Compound
- the following Tests demonstrate the regrowth inhibition efficacy of the compounds of Formula 1 in cotton crops.
- the regrowth inhibition afforded by the compounds is not limited, however, to this species.
- Cotton seeds (cv. 'Fibermax FM 989 RR') were planted in mid spring season, 3.8 cm deep in a clay soil having 1.8 % organic matter and a pH of 6.8. Plots were 9 m long by 3 ra wide with rows spaced 96.5 cm apart. Seeds were spaced 10.2 cm apart within the rows.
- the field was managed using conventional tillage practices, and applications of herbicides and insecticides were used to maintain a healthy crop. The plots were arranged in a randomized complete block design with each treatment being replicated three times.
- Treatments were applied preharvest over the top of the crop in late summer, when approximately 65 % of the bolls had opened, using a backpack sprayer delivering a spray volume of 140 L/ha using a pressure of 276 kPa.
- Treatments consisted of the commercial harvest aids tribufos and ethephon + AMADS alone and in combination with Compound 4, dissolved or suspended in water.
- the effects on the treated plants and untreated controls were recorded 4, 11 and 21 days after application. Plants were visually evaluated for harvest aid effects of boll opening, defoliation, desiccation, and whole plant (basal and terminal) regrowth inhibition. Results were calculated as the mean of the three replicates, based on a scale of 0 to 100 where 0 is no effect and 100 is complete expression of the effect.
- a field trial was conducted to evaluate the effects of mixtures of Compound 4 with commercial harvest aids on cotton (GOSHI, Gossypium hirsutum L.). Delta and Pine Land Co. cotton seeds (cv. 'DP 434') were planted in mid spring season, 3.8-cm deep in a fine- texture loam soil comprising 40 % sand, 36 % silt, and 24 % clay. Soil organic matter was 1.8 %; pH was 6.6. Plots were 9.1 m long by 3.0 m wide with rows spaced 96.5 cm apart. Seeds were spaced 10.2 cm apart within the rows. The field was managed using conventional tillage practices, and applications of herbicides and insecticides were used to maintain a healthy crop.
- Treatments were applied preharvest over the top of the crop in late summer, when approximately 65 % of the bolls had opened, using a tractor-mounted sprayer delivering a spray volume of 140 L/ha at a pressure of 241 kPa.
- Treatments consisted of the commercial harvest aids tribufos, ethephon, and ethephon •4-AMADS alone and in combination with Compound 4, dissolved or suspended in water. Plants were evaluated for harvest aid effects including defoliation and regrowth inhibition at 4, 7 ', 14, and/or 22 days after application (DAA). Individual results were recorded and data reported as the means of the three replicates.
- a field trial was conducted to evaluate the effects of mixtures of Compound 4 with commercial harvest aids on cotton (GOSHI, Gossypium hirsutum L.). Delta and Pine Land Co. cotton seeds (cv. 'DP 117BRHRF') were planted in mid spring season, 2.0-cm deep in a clay soil. Plots were 12.19 m long by 3.86 m wide with rows spaced 96.5 cm apart. The field was managed using conventional tillage practices, and applications of herbicides and insecticides were used to maintain a healthy crop. The plots were arranged in a randomized complete block design with each treatment being replicated four times.
- Treatments were applied preharvest over the top of the crop in late summer, when approximately 65 % of the bolls had opened, using a tractor-mounted sprayer delivering a spray volume of 140.3 L/ha at a pressure of 193 kPa. Treatments consisted of the commercial harvest aids tribufos, ethephon, and ethephon + AMADS alone and in combination with Compound 4, dissolved or suspended in water. Plants were evaluated for harvest aid effects including defoliation and regrowth inhibition at 4, 7, and 14 DAA. Individual results were recorded and data reported as the means of the three replicates. Results for Tests A, Bl and B2 are given in Table A, Bl and B2 respectively.
- Plants were visually evaluated for harvest aid effects of boll opening, defoliation, desiccation, and whole plant (basal and terminal) regrowth inhibition.
- Sty of Defoliation (%) represents a visual rating at a given DAA of the overall reduction in foliage on treated plants in a plot. It is based on a scale of 0 to 100%, where 0 represents an amount of foliage similar to control plants, and 100 indicates no leaves present. Plant regrowth assessments at a given DAA were made relative to appropriate controls after effects of defoliation were observed.
- Regrowth of the basal ("plant stalk”, below the top 15.3 cm of the plants) and termina) ("plant terminal", top 15.3 cm of the plants) portions of the plants were separately evaluated on a visual rating scale of 0 to 100%, where 0 indicates no regrowth, and 100 indicates complete regrowth.
- the regrowth evaluations involved overall assessment of renewed or continued growth and development, which included: node and intemodal development and elongation, and leaf formation, development and growth. These regrowth evaluations were recorded as “Regrowth %” and subsequently converted in the tables to "Regrowth Inhibition (%)", which was calculated as 100% - YT, where Y T equals the mean Regrowth % of three replicates for a respective treatment.
- Application rates are grams active ingredient per hectare (g a.i./ha).
- a Application rates are grams active ingredient per hectare (g a.i./ha).
Abstract
Description
Claims
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US12/158,694 US20090247404A1 (en) | 2006-02-02 | 2007-01-26 | Method for improving harvestability of crops |
BRPI0706884-0A BRPI0706884A2 (en) | 2006-02-02 | 2007-01-26 | method of inhibiting cotton plant foliage growth, mixing to cause prolonged defoliation of cotton plant and agricultural compositions |
AU2007212702A AU2007212702A1 (en) | 2006-02-02 | 2007-01-26 | Method for improving harvestability of crops |
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US76453906P | 2006-02-02 | 2006-02-02 | |
US60/764,539 | 2006-02-02 | ||
US76554206P | 2006-02-06 | 2006-02-06 | |
US60/765,542 | 2006-02-06 |
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WO2007092184A3 WO2007092184A3 (en) | 2008-12-31 |
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US (1) | US20090247404A1 (en) |
AU (1) | AU2007212702A1 (en) |
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Also Published As
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BRPI0706884A2 (en) | 2011-04-12 |
AU2007212702A1 (en) | 2007-08-16 |
US20090247404A1 (en) | 2009-10-01 |
WO2007092184A3 (en) | 2008-12-31 |
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