Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
  • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D257/04—Five-membered rings
• • 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
  • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
  • C07C331/16—Isothiocyanates
  • C07C331/28—Isothiocyanates having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings

Definitions

• This invention concerns novel selective herbicides.
• R 14 and R 15 are independently selected from a list including hydrogen and alkylsulfonyl (preferably of 1 to 4 carbon atoms), being for example NHSO 2 CH 3 .
• the present invention provides herbicidal compounds including the compound of the formula
• Soybean (Glycine max) 0 0 Corn (Zea mays) 0 0 Morningglory (Ipomea spp.) 45 0 Pitted Morningglory 10 0 Jimsonweed (Datura stramoniam) 60 40
• Wildmustard (Brassica kaber) 100 65 Sesbania (Sesbania exaltata) 80 25 Prickly Sida (Sida apinosa) 85 20
• the compound is particularly useful in combination with other herbicides such as 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidone, trifluralin (i.e. N,N-dipropyl-alpha, alpha, alpha-trifluoro-2,6-dinitro-p-toluidine), tridiphane (i.e. 2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane), alachlor (i.e.
• 2-chloro-2',6'-diethyl-N-(methoxymethyl)acetanilide or any of the following: isoproturon bentozon chlortoluron acifluorfen-sodium clopyralid chlorpropham bromoxynil imazaquin pyridate 2,4-DB bifenox paraquat chlorsulfuron glyphosate dichlofop-methyl vernolate difenzoquat chlorimuron dicamba atrazine dinoseb cyanozine triallote simazine barban EPTC
• the pre-emergence application of the tetrazolinone herbicide may be combined with a sequential, post-emergent treatment with another herbicide such as one of the known grass-controlling herbicides which show a favorable selectivity for the particular crop.
• Such post-emergence treatment may be made, say, one or two weeks or more (e.g. a month) after the emergence of the crop.
• Herbicides that may thus be applied sequentially in combination with the pre-emergence application of the tetrazolinone include such materials as the ethyl ester of 2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-propionic acid; sethoxydim; haloxyfop-methyl; and quinofop-ethyl.
• compositions for pre-emergence application were formulated by mixing Aqueous Suspension A (described below) with Flowable Concentrate B (also described below) and water, the relative proportions and rates of application being such that the active ingredients were applied at rates shown in Table B, below, to the field planted with soybeans:
• Active ingredient A (Compound No. 4) 4.92
• the antimicrobial agent is sodium o-phenylphenate tetrahydrate sold under the trademark and designation "Dowacide A”.
• the foam suppressant is a water dilutable silicone emulsion sold under the trademark and designation "Dow Corning AF”.
• Surfactant C i s a non-ionic paste of a condensate of ethylene oxide with a hydrophobic base formed by condensing propylene oxide with propylene glycol, sold under the trademark and designation "Pluronic P-84.”
• Surfactant D is an anionic liquid comprising the sodium salt of a complex organic phosphate ester, sold under the trademark and designation "GAFAC LO-529.”
• the thickener is a xantham gum sold under the trademark and designation "Kelzan-M”.
• the suspending agent is a colloidal magnesium aluminum silicate sold under the trademark and designation "Veegum.” To prepare this Suspension A, all the ingredients, except the thickener and some 4/10 of the total water, are ground together after which the thickener and the balance of the water are added.
• Plant Species % Control is a highly selective herbicide for use with cotton or soybeans particularly for preemergence application at rates below about 1/4 or 1/10 kg/ha (such as rates of 0.06, 0.03 or 0.015 kg/ha). Its effectiveness is indicated by the following data for percent control on preemergence application of the compound at a rate of 0.0313 kg/ha in the greenhouse. Plant Species % Control
• Sesbania (Sesbania exaltata) 100
• Proso Millet (Panicum miliaceum) 90 The sulfonamides disclosed herein which have a hydrogen on the nitrogen of the sulfonamide group are acids and, as taught in the published PCT International application no. WO 85/01939 may be converted into a salt such as a sodium, potassium, calcium, ammonium, magnesium or mon-, di- or tri(C 1 to C 4 ) alkyl ammonium salt which may also be used, in that form, as the herbicide.
• a salt such as a sodium, potassium, calcium, ammonium, magnesium or mon-, di- or tri(C 1 to C 4 ) alkyl ammonium salt which may also be used, in that form, as the herbicide.
• Other suitable herbicidal salts of these sulfonamides are the sulfonium or sulfoxonium salts, such as salts of bases of the formula
• R 30 may be alkyl (such as straight chain or branched chain lower alkyl, e.g. methyl, ethyl, propyl), haloalkyl (such as CF 3 or
• dialkylamino aryl (such as phenyl, optionally substituted with one or more of: halogen such as Cl, Br or F; alkyl such as lower alkyl, e.g. methyl; alkoxy such as lower alkoxy; e.g.
• R 31 may be hydrogen, alkyl (e.g. straight or branched chain lower alkyl such as methyl, ethyl, propyl, isopropyl or butyl), benzyl, haloalkyl (e.g.
• alkoxy e.g. methoxy
• alkynyl such as propargyl
• alkenyl such as allyl
• a group of the formula -alkylene-SO 2 R 30 in which, for example, said alkylene group (e.g. -CH 2 -) has 1 to 4 carbon atoms, alkoxymethyl (such as methoxymethyl), cyanpmethyl, carboxymethyl (including salts thereof) or alkoxycarbonylmethyl.
• R 30 and R 31 together may be a divalent radical such as alkylene (e.g. of 1 to 10 carbon atoms such as methylene or 1,3-propylene).
• R 31 may also be a salt-forming group such as a metal (e.g. Na, K or Ca) or ammonium (e.g. NH 4 or lower alkyl-substituted ammonium) or sulfonium or sulfoxonium, as previously discussed.
• R may be alkyl (preferably of 1 to 6 carbon atoms), haloalkyl (preferably of 1 to 5 carbon atoms), alkoxyalkyl (preferably of 2 to 6 carbon atoms), alkylthioalkyl (preferably of 2 to 6 carbon atoms), cyanoalkyl (preferably of 1 to 5 alkyl carbon atoms), haloalkoxyalkyl (preferably of 2 to 6 carbon atoms), trifluoromethylthio, alkenyl (preferably of 2 to 5 carbon atoms), or haloalkenyl (preferably of 2 to 5 carbon atoms).
• any alkyl, alkenyl, alkynyl or alkylene radical have less than 6 carbon atoms; and that X 1 be
• F or Cl and X 2 be Cl or Br.
• the compounds in which Z is N(R 31 )SO 2 R 30 may be prepared by the use of steps generally described in the literature or in the following Examples or by methods analogous or similar thereto and within the skill of the art.
• Example I an arylamine is treated to form the corresponding aryl isocyanate whose isocyanate portion is then modified to form a tetrazolinone ring. Thereafter the benzene ring of the intermediate is nitrated, the nitro group is reduced to form an amino group, which is then treated with R 30 SO 2 Cl or (R 30 SO 2 ) 2 O to convert it to an -N(R 31 )SO 2 R group (e.g.
• R 31 is a salt-forming group (e.g. Na); this may then be treated with an acid to form the corresponding (acidic) -NHSO 2 R 30 group.
• subsequent alkylation as by treatment with the appropriate alkyl iodide as in
• Example VI forms the corresponding R 30 group.
• the reaction sequence involves R 30 SO 2 Cl treatment of an intermediate having hydrogen on the 4-nitrogen of the tetrazolinone ring, that hydrogen may also be replaced, during such treatment, by R 30 SO 2 - to form an intermediate (such as a compound which has three R 30 SO 2 - groups) from which the R 30 SO 2 - group on said 4-nitrogen may be removed readily by the treatment with the base, after which the appropriate R group may be substituted on said 4-nitrogen.
• the sequence of steps may be changed.
• a ni troaniline such as 3-nitroaniline or 2-fluoro-5-nitroaniline
• make the corresponding isocyanate and convert the isocyanate group to a tetrazolinone ring (as by treatment with trimethylsilylazide) and then reduce the nitro group and substitute an R group on N-4 of the tetrazolinone ring, in either order.
• the amino group may be converted to a N(R 31 )SO 2 R 30 group, after which the compound may be halogenated (as with SO 2 Cl 2 in dioxane) to place a halogen at the 4-position of the benzene ring (or, when the intermediate being halogenated does not yet have the halogen on its 2-position, this halogenation may place halogen atoms at both the 2- and 4-positions of the benzene ring).
• the following series of successive intermediates may be prepared from 2-fluoro-5-nitroaniline: 2-fluoro-5-nitrophenyl isocyanate;
• 2-fluoro substituent may be formed, and the last intermediate may then be treated to place the halogens at its 2- and 4-positions of its benzene ring.
• This may be chlorinated to form the compound of Example I Step C, below.
• a series of reactions e.g. by reducing the NO 2 group to an amino group and then
• the conversion of the amino group to the tetrazolinone ring may be effected through formation of the isocyanate in the manner illustrated in Example I (thus forming 2-fluoro-5-(bis (N-ethylsulfonyl)amino)phenyl isocyanate) or through intermediate formation of a tetrazolinethione as discussed below.
• 2-fluoro-5-nitroaniline one may produce (either through the previously mentioned 2-fluoro-5-nitrophenyl isocyanate or through a corresponding tetrazolinethione as discussed below) the previously mentioned 1-( 2-fluoro-5-aminophenyl)-1,4-dihydro-5H-tetrazol-5-one.
• Example VIII In another route from the same 2-fluoro-5-nitroaniline starting material, one may (as illustrated in Example VIII) acetylate the NH 2 to protect it; then reduce the nitro group to form an amino group; chlorinate and treat with alkylsulfonyl chloride in any order (to form, e.g., 2-fluoro-4-chloro-5- ( ethylsulfonylamino)-acetanilide); then hydrolyze off the acetyl group to form 2-fluoro-4-chloro-5-(ethylsulfonylamino)aniline, whose free NH 2 group may then be converted (e.g.
• alkylsulfonate e.g. 2-fluoro-4-chloro-5-bis ( N-ethylsulf onylamino ) acetanilide ( m .p . 218-219°C) and/or 2-fluoro-4-chloro-5-(N-ethylsulfonylamino) acetanilide.
• the aryl tetrazolinethione may then be converted to the corresponding aryl tetrazolinone as by the method illustrated in Example VII below in which the aryl tetrazolinethione is reacted with a base and an alkyl halide to produce an aryl tetrazolyl alkyl sulfide, which is then treated with a base to form the aryl tetrazolinethione.
• To form the aryl tetrazolinethione from the arylamine one may react the latter with thiophosgene to form the aryl isothiocyanate and then react that isothiocyanate with an azide (e.g. with sodium azide in water at room temperature).
• an azide e.g. with sodium azide in water at room temperature
• intermediates such as the following may be produced: sodium N-(2-fluoro-5-nitrophenyl)dithiocarbamate;
• 2-fluoro-5-nitrophenyl isothiocyanate 1-(2-fluoro-5-nitrophenyl)-1,4-dihydro-5H-tetrazol-5-thione and its sodium salt; sodium N-(4-chloro-2-fluorophenyl)dithiocarbamate; 4-chloro-2-fluorophenyl isothiocyanate;
• salts may be made and used instead of the sodium salts (of, say, the thione or the dithiocarbamate), e.g. salts of other alkali metals or onium salts (e.g. triethylammonium salt).
• reaction with R 30 SO 2 Cl or (R 30 SO 2 ) 2 O may be effected at, for instance, a temperature below 60°C such as -10 to 50°C in the presence of a suitable base and an inert solvent.
• the halogenation reaction with chlorine or bromine may be effected at, for instance, a temperature of about 20 to 150°C.
• the introduction of the fluoropropyl group may be effected at, for instance, about 20 to 130°C, preferably by reacting fluoropropyl- X 6 wherein X 6 is a leaving group, e.g. 1-bromo-3-fluoropropane, 1-chloro-3-fluoropropane or 3-fluoropropyl methane sulfonate in the presence of a suitable base (e.g. NaOH) and a suitable solvent (e.g. N,N-dimethylformamide or acetone).
• a suitable base e.g. NaOH
• a suitable solvent e.g. N,N-dimethylformamide or acetone
• reaction mixture was cooled to 10°C and 0.9 g (0.007 mole) of ethanesulfonyl chloride was added dropwise. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it stirred for 16 hours. The reaction mixture was poured into ice-water and the organic layer separated. The organic layer was concentrated under reduced pressure to a residue. The residue was dissolved in methylene chloride and subjected to column chromatography on silica gel.
• the resultant solution was extracted with 100 ml of a dilute, aqueous, sodium hydroxide solution.
• the extract was washed with 50 ml of methylene chloride and was neutralized with concentrated hydrochloric acid.
• This aqueous solution was extracted several times with ethyl acetate and the extracts were combined.
• the combined extract was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under the reduced pressure to leave a thick oil.
• Step B 1-[4-Chloro-2-fluoro-5-(N-trifluoromethylsulfonylamino)phenyl]-1,4-dihydro-4-(3- fluoropropyl)-5H-tetrazol-5-one potassium salt
• the reaction mixture was stirred for 15 minutes and 0.5 g (0.003 mole) of 1-iodopropane was added. This mixture was stirred at room temperature for approximately 18 hours.
• the mixture was diluted with diethyl ether and washed in succession with an aqueous, 10% sodium hdyroxide solution and an aqueous, saturate dsodium chloride solution.
• the washed organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to leave an oily residue.
• Step A Triethylamm ⁇ nium salt of 4-chloro-2- fluorophenyl dithiocarbamic acid
• a solution of 30.0 g (0.206 mole) of 4-chloro-2-fluoroaniline and 30 ml (0.215 mole) of triethylamine in 90 ml of carbon disulfide was stirred at room temperature for 22 hours, resulting in a thick suspension.
• the reaction mixture was filtered.
• the filter cake was washed with diethyl ether to yield 56.1 g of the triethylammonium salt of 4-chloro-2-fluorophenyl dithiocarbamic acid as a yellow solid.
• Step B 1-(4-Chloro-2-fluorophenyl)-1,4-dihydro-5H- tetrazol-5-thione
• Steps A-C were repeated to prepare additional 2-fluoro-5-bis(N-ethylsulfonylamino)acetanilide.
• Step D 2-Fluoro-5-(N-ethylsulfonylamino)acetanilide
• a solution of sodium hydroxide 5.65 g, (0.0141 mole) in 20 ml of water.
• the dioxane solvent was removed from the solution by extraction with diethyl ether. The remaining aqueous phase was acidified with concentrated hydrochloric acid forming a precipitate.
• Step E 4-Chloro-2-fluoro-5-(N-ethylsulfonylamino) acetanilide
• Step F 4-Chloro-2-fluoro-5-(N-ethylsulfonylamino)aniline
• a stirred mixture of 2.0 g (0.0068 mole) of 4-chloro-2-fluoro-5-(N-ethylsulfonylamino) acetanilide and 0.84 g (0.020 mole) of sodium hydroxide in 100 ml of water was heated at reflux for approximately 18 hours.
• the reaction mixture was cooled and neutralized with concentrated hydrochloric acid.
• the neutralized mixture was extracted with ethylacetate.
• the extract was washed with an aqueous, saturated sodium chloride solution.
• the washed extract was dried over anhydrous magnesium sulfated and filtered.
• the filtrate was evaporated under reduced pressure to yield 2.7 g of 4-chloro-2-fluoro-5-(N-ethylsulfonylamino)aniline as a solid.
• the nmr was consistent with the proposed structure.
• Step G 4-Chloro-5-(N-ethylsulfonylamino)-2- fluorophenylisothiocyanate
• Herbicidal data at selected application rates are given for various compounds of the invention in the tables below.
• the test compounds are identified in the tables of herbicidal data below by numbers which correspond to those used above in those tables. "kg/ha" is kilograms per hectare.
• the active compounds are formulated into herbicidal compositions by admixture in herbicidally effective amounts with adjuvants and carriers normally employed in the art for facilitating the dispersion of active ingredients for the particular utility desired, recognizing the fact that the formulation and mode of application of a toxicant may affect the activity of the material in a given application.
• the present herbicidal compounds may be formulated as granules of relatively large particle size, as water-soluble or water-dispersible granules, as powdery dusts, as wettable powders, as emulsifiable concentrates, as solutions, or as any of several other known types of formulations, depending on the desired mode of application.
• herbicidal compositions may be applied either as water-diluted sprays, or dusts, or granules (e.g. for paddy rice) in the areas in which suppression of vegetation is desired.
• These formulations may contain as little as 0.1%, 0.2% or 0.5% to as much as 95% or more by weight of active ingredient.
• Dusts are free flowing admixtures of the active ingredient with finely divided solids such as talc, natural clays, kieselguhr, flours such as walnut shell and cottonseed flours, and other organic and inorganic solids which act as dispersants and carriers for the toxicant; these finely divided solids have an average particle size of less than about 50 microns.
• a typical dust formulation useful herein is one containing 1.0 part or less of the herbicidal compound and 99.0 parts of talc.
• Wettable powders also useful formulations for both pre- and postemergence herbicides, are in the form of finely divided particles which disperse readily in water or other dispersant.
• the wettable powder is ultimately applied to the soil either as a dry dust or as an emulsion in water or other liquid.
• Typical carriers for wettable powders include Fuller's earth, kaolin clays, silicas, and other highly absorbent, readily wet inorganic diluents. Wettable powders normally are prepared to contain about 5-80% of active ingredient, depending on the absorbency of the carrier, and usually also contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion.
• a useful wettable powder formula- tion contains 80.8 parts of the herbicidal compound, 17.9 parts of Palmetto clay, and 1.0 part of sodium lignosulfonate and 0.3 part of sulfonated aliphatic polyester as wetting agents.
• Other wettable power formulations are: Component: % by Wt.
• Active ingredient 90 Dioctyl sodium sulfosuccinate 0 . 10 Synthetic fine silica 9 . 90 Total 100 . 00
• ECs emulsifiable concentrates
• ECs emulsifiable concentrates
• ECs emulsifiable concentrates
• these concentrates are dispersed in water or other liquid carrier, and normally applied as a spray to the area to be treated.
• the percentage by weight of the essential active ingredient may vary according to the manner in which the composition is to be applied, but in general comprises 0.5 to 95% of active ingredient by weight of the herbicidal composition.
• Component % by Wt
• Active ingredient 53.01 Blend of alkylnaphthalenesulfonate and polyoxyethylene ethers 6.00 Epoxidized soybean oil 1.00
• Active ingredient 10.00 Blend of alkylnaphthalenesulfonate and polyoxyethylene ethers 4.00
• Flowable formulations are similar to ECs except that the active ingredient is suspended in a liquid carrier, generally water.
• Flowables like ECs, may include a small amount of a surfactant, and contain active ingredient in the range of 0.5 to 95%, frequently from 10 to 50%, by weight of the composition.
• flowables may be diluted in water or other liquid vehicle, and are normally applied as a spray to the area to be treated.
• Typical wetting, dispersing or emulsifying agents used in agricultural formulations include, but are not limited to, the alkyl and alkylaryl sulfonates and sulfates and their sodium salts; alkylaryl polyether alcohols; sulfated higher alcohols; polyethylene oxides; sulfonated animal and vegetable oils; sulfonated petroleum oils; fatty acids esters of polyhydric alcohols and the ethylene oxide addition products of such esters; and the addition product of long-chain mercaptans and ethylene oxide.
• the surface-active agent when used, normally comprises from 1 to 15% by weight of the composition.
• compositions include simple solutions or suspensions of the active ingredient in a relatively non-volatile solvent such as water, corn oil, kerosene, propylene glycol, or other suitable solvents.
• a relatively non-volatile solvent such as water, corn oil, kerosene, propylene glycol, or other suitable solvents.
• Oil Suspension % by Wt.
• compositions for herbicidal applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene, or other organic solvents.
• Granular formulations wherein the toxicant is carried on relatively coarse particles, are of particular utility .for aerial distribution or for penetration of cover crop canopy.
• Pressurized sprays typically aerosols wherein the active ingredient is dispersed in finely divided form as a result of vaporization of a low boiling dispersant solvent carrier, such as the Freons, may also be used.
• Water-soluble or water-dispersible granules are also useful formulations for herbicidal application of the present compounds. Such granular formulations are free-flowing, non-dusty, and readily water-soluble or water-miscible.
• the soluble or dispersible granular formulations described in U.S. patent No. 3,920,442 are useful herein with the present herbicidal compounds.
• the granular formulations, emulsifiable concentrates, flowable concentrates, solutions, etc. may be diluted with water to give a concentration of active ingredient in the range of say 0.1% or 0.2% to 1.5% or 2%.
• the active herbicidal compounds of this invention may be formulated and/or applied with insecticides, fungicides, nematicides, plant growth regulators, fertilizers, or other agricultural chemicals and may be used as effective soil sterilants as well as selective herbicides in agriculture.
• an effective amount and concentration of the active compound is of course employed; the amount may be as low as, for example, 7 g/ha or lower.
• the active herbicidal compounds of this invention may be used in combination with other herbicides, e.g. they may be mixed with, say, an equal or larger amount of a known herbicide such as chloroacetanilide herbi- cides such as 2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide (alachlor), 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide (metolachlor), and N-chloroacetyl-N-(2,6-diethylphenyl)glycine (diethatyl-ethyl); benzothiadiazinone herbicides such as 3-(1-methylethyl)-(1H)-2,1,3-benzothiadiazin-4-(3H)-one-2,2-dioxide (bentazon); triazine herbicides such as 6-chloro-
• Z is ethylsulfonylamino
• compounds 4, 31, 34 have been found to be particularly useful when used pre-emergently against broad leaf weeds with crops such as corn, rice, wheat and soybeans.
• Compound 4 also shows very good control of broadleaf weeds in plantings of such crops as corn, wheat, barley, oats, rice and sorghum when applied post-emergently.
• rates of application in the field may be, for instance, in the range of about 30 to 250 g/ha, e.g., 125 g/ha.
• Field Bindweed 100 100 20 40 100
• Morningglory 100 100 60 60 100 100 100
• Velvetleaf 100 95 100 100 100 100 100
• Wheat 80 100 100 100 100 60
• Field Bindweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100
• Morningglory 100 100 95 100 100 100 100 100 100
• Johnsongrass 90 100. 100 100 100 90
• Soybean 10 10 20 20 60 10
• Morningglory 10 60 100 100 70 60
• Velvetleaf 20 100 100 100 100 100 100 100 100 100 100 100
• Field Bindweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100
• Morningglory 100 100 100 100 100 90
• Velvetleaf 100 100 100 100 100 100 95
• Field Bindweed 20 95 70 40 100 80 100
• Morningglory 20 100 100 70 100 70 100 70 100
• Field Bindweed 100 100 70 30 100
• Morningglory 100 95 100 40 100 100 100
• Velvetleaf 100 100 100 95 100 100 100
• Wheat 70 80 100 100 100 60
• Field Bindweed 100 100 100 100 80 100
• Morningglory 80 100 100 100 100 100 100 100 100 100 100 100
• Morningglory 100 100 70 80 100
• Field Bindweed 100 100 100 95 60 40
• Morningglory 100 100 100 100 80 50
• Velvetleaf 100 100 100 100 90 80
• Field Bindweed 100 100 40 100 80 100
• Morningglory 100 100 60 100 90 100
• Velvetleaf 100 100 70 95 100 100

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• 1986
  • 1986-12-22 ZA ZA869640A patent/ZA869640B/xx unknown
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  • 1986-12-23 BR BR8607060A patent/BR8607060A/pt not_active Application Discontinuation
  • 1986-12-23 JP JP87502992A patent/JPS63500382A/ja active Pending
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  • 1986-12-23 AU AU75418/87A patent/AU588120B2/en not_active Ceased
  • 1986-12-23 EP EP19870904008 patent/EP0252982A4/en not_active Withdrawn
  • 1986-12-23 WO PCT/US1986/002795 patent/WO1987003873A1/en not_active Application Discontinuation
  • 1986-12-23 KR KR1019870700773A patent/KR900002682B1/ko not_active IP Right Cessation
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• 1987
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• 1988
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