Classifications

• • 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
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group

Definitions

• An effervescent tablet produces gas bubbles by the reaction between an acid and a base. Should the water level in the tablet exceed about 0.1%, the tablet will begin to lose its effervescence even though it is stored in its container. Normally, an amount of water exceeding 0.1% is required to formulate a tablet having acceptable integrity and strength.
• One way to keep the water employed during formulation from ruining the tablet during long-term storage is to package the tablet with a desiccant.
• the water in the tablet diffuses out and is taken up by the desiccant. This water is held by the desiccant and so cannot cause the acid/base reaction to occur.
• CA-A-2,013,918 discloses a tablet comprising potassium carbonate and/or potassium bicarbonate as bases and a desiccant which physically adsorbs water.
• WO 88/09161 discloses an effervescent tablet for cleaning dentures comprising pancreatin, an acid component, a base component, and a drying agent.
• This invention comprises a tablet formulation consisting essentially of by total weight of the formulated composition:
• the desiccant being (A) when (b) is potassium carbonate or potassium bicarbonate.
• This delivery system is characterized by the inter-relationship of components (a) to (f) in the recited ranges to effect rapid disintegration of finely dispersed pesticide particles (i).
• Preferred ranges of the composition are 5% to
• tablette formulation is meant the tablet made from the composition described herein, as well as the composition formulated in accordance with this disclosure but not in tablet form.
• the preferred tablet formulation of the present invention is in the form of a tablet.
• Contemplated pesticides include those selected from the following classes, including mixtures thereof: herbicides, fungicides, bactericides, insecticides, nematocides, acaricides, and growth regulants.
• Preferred dibasic and tribasic organic carboxylic acids include citric, fumaric, phthalic, maleic, malic, oxalic, adipic, glutaric, 2-methyl glutaric, succinic, and tartaric, or mixtures of any of them.
• dispenserants includes sodium, potassium, ammonium and calcium salts of naphthalene sulfonic acid-formaldehyde condensates; lithium, sodium, potassium, calcium, and ammonium salts of lignosulfonates; sodium; potassium and ammonium salts of polyacrylates and carboxylates; sodium salts of maleic a-nhydride-isobutylene copolymers; and water soluble nonionic polymers such as polyvinyl-pyrrolidone, polyethylene oxides and cellulose derivatives.
• Preferred dispersants include the sodium, potassium, ammonium and calcium salts of naphthalene sulfonic acid-formaldehyde condensates, with the ammonium salts more preferred.
• Water-insoluble, cross-linked polyvinylpolypyrrolidone disintegrant refers to any of the generic, but is not limited to. crospovidone disintegrating agents.
• anionic wetting agent includes, but is not limited to, salts of alkylbenzene sulfonates, alkyl and dialkylnaphthalene sulfonates, alkyl and alcohol sulfates, sulfoalkylamides, carboxylates, alpha-olefin sulfonates and dialkyl sulfosuccinates.
• nonionic wetting agent includes acetylenic diols, ethylene oxide-propylene oxide copolymers, alkylphenol ethoxylates, fatty acid ethoxylates, alcohol ethoxylates, sorbitan fatty acid ester ethoxylates and castor oil ethoxylates.
• the preferred wetting agents are sodium dialkyl sulfosuccinates of which sodium diisobutyl sulfosuccinate, sodium diamyl sulfosuccinate and sodium dicyclohexyl sulfosuccinate are more preferred.
• the internal desiccants that "chemically bind" water are those that actually undergo chemical reactions with water to form a new compound.
• An example of this type of material is CaO which reacts with water to form Ca(OH) 2 .
• Other materials representative of those which react in this manner are magnesium oxide and boric anhydride.
• the internal desiccants that "physically adsorb" water are. those selected from the group consisting of highly-dispersed silicilic acids such as silica gel; aluminum oxide; clays such as montmorillonite; and amorphous and crystalline aluminosilicates such as molecular sieves and zeolites. Combinations of these desiccants with those that form hydroxides and hydrates can be used. Kirk- Othmer's Encyclopedia of Chemical Technology (3rd ed., Nol. 8, p 115) describes desiccants suitable for use in the tablet formulation of this invention as Type 1 and Type 4 desiccants. Either type can be employed, singly or in combination, as long as the desiccant does not expand when it picks-up water. Such expansion causes the tablet to crack or crumble on long term storage.
• Internal desiccants useful in the tablet formulation of this invention also include materials that chemically bind water, not in the sense of a Chemical reaction that forms a hydroxide, but in the sense of a chemical reaction that produces a hydrate.
• useful desiccants that form hydrates are CaSO 4 , ⁇ aOAc, MgSO 4 , ⁇ a 2 SO 4 , CaCl 2 , and ZnSO 4 .
• Representative of the hydrate-forming reaction is that undergone by CaCl 2 to form CaCl 2 .H 2 O.
• One or more desiccants from each group, the hydroxide-forming and the hydrate- forming, can be employed, alone or in combination, depending on the particular properties sought by the formulator. In any event, the desiccants employed in the tablets of this invention are not those of the water-adsorbing type employed in prior art tablet formulations. Kirk-Othmer's Encyclopedia of Chemical
• a preferred tablet formulation is one wherein component (b) is an ammonium, sodium or lithium carbonate or bicarbonate or mixture thereof, and the internal desiccant is selected from (A), (B) and a mixture of (A) and (B).
• (b) is potassium carbonate or bicarbonate or mixture thereof, and the internal desiccant is (A).
• Preferred pesticides are those having a melting point of at least about 100°C and solubility in pH 7 water at 20°C of no more than about 5% by weight.
• herbicides such as: acifluorfen, asulam, atrazine, bensulfuron, bentazon, bromacil, bromoxynil, chloramben, chlorimuron ethyl, chloroxuron, chlorsulfuron, chlortoluron, clomazone, cyanazine, dazomet, desmediphan, dicamba, dichlobenil, dichlorprop, diphenamid, dipropetryn, diuron, thiameturon, 2-[[[[[N-(4-methoxy-6-methyl-1,3,5-triazine-2-yl)-N- methylamino]carbonyl]amino]sulfonyl]benzoic acid, methyl ester, fenac, fenuron, fluometuron, fluridone, fomesafen, glyphosate, hexazinone,imazamethabenz, imazaquin, imazeth
• fungicides such as: carbendazim, thiuram, dodine, chloroneb, cymoxanil, captan, folpet, thiophanatemethyl, thiabendazole, chlorothalonil, dichloran, captafol, iprodione, vinclozolin, kasugamycin, triadimenol, flutriafol, flusilazol, hexaconazole or fenarimol; bactericides such as oxytetracycline dihydrate;
• acaricides such as: hexathiazox, oxythioquinox, dienochlor or cyhexatin;
• insecticides such as: carbofuran, carbaryl, thiodicarb or deltamethrin.
• More preferred pesticides are hexazinone, 2,4-D, chlorsulfuron,
• the most preferred pesticides are sulfonylurea herbicides such as
• the most common method for applying water insoluble pesticides is as fine aqueous dispersions which are sprayed onto the field or crop using ground or aerial spray rigs.
• the tablets of this invention combine a high level of physical integrity with rapid break-up in water using minimal or no agitation while providing fine dispersions of active ingredient. Since the spray nozzles are typically protected against clogging by 50 mesh screens (U.S. mesh size), the dispersions must be fine enough to pass through this size screen without plugging it. This ability is characteristic of pesticide dispersions delivered by the delivery system of tfiis invention.
• High physical integrity of the tablets is desirable so that the tablets themselves can withstand the tabletting operation and survive handling, packaging and shipping without breaking.
• An axial breaking strength of greater than about 9x10 3 newtons is generally necessary for a tablet to survive such treatment.
• the tablets of the invention disperse completely in less than 10 minutes, most in less than 5 minutes using even the cold water drawn from wells in the early spring.
• a dispersant is required so that the particles of the active ingredient formed during the disintegration of the tablet remain separated in the cold, hard water.
• the disintegrant allows the penetration of the water into the interior of the tablet through a wicking or swelling action.
• Common starch or cellulose-based disintegrants are unsuitable in agricultural applications as they typically form gels on the 50 mesh spray nozzle screens.
• a water insoluble cross-linked polyvinylpolypyrrolidone is used.
• a wetting agent is required to control the size of the carbon dioxide bubbles formed during the reaction of the acid base.
• the wetting agent reduces the surface tension between the bubbles and the solid tablet resulting in the formation of smaller bubbles which readily detach from the tablet surface.
• the tablet remains submerged in the water for a longer period of time, thus improving contact of the entire tablet surface with water.
• Inert ingredients up to 99.9% of the total weight of the composition can be employed.
• Inert fillers such as sugar or clay can be added as long as they do not affect the chemical stability of the active ingredient(s).
• Materials such as glidants, anti-adherents, and lubricants can also be employed to facilitate production in the tablet press. The amounts and types of such ingredients will be readily determinable by one skilled in the tabletting art given the disclosure herein.
• the formulation ingredients are typically ground and mixed in a mill, e.g., an air or hammermill.
• the ground premix is passed through a 50 or 100 mesh (U.S.A. Standard Sieve Series) screen.
• the average particle size of the ground premix should be in the range of 5 to 15 microns. If it is much smaller, the tablet will be strong, but will not break up very fast. If the premix is much larger, the dispersion will not be fine enough to pass a wet screen test used to indicate whether the dispersion will clog the spray nozzle and protective screen discussed previously.
• the tablets can be prepared using conventional tablet-making equipment. Their diameter can vary from about 1 cm or less, to 7.5 cm, depending on the tablet weight desired. Flat-faced, beveled-edge punches, with or without a breakline, product attractive tablets.
• a lubricant such as magnesium stearate or boric acid can be used. Such lubricants and anti- adherents can be brushed onto the die surface or incorporated into the
• Tablets have been formed in a hydraulic press with a capacity of 18,000 kg of force. Pressures between about 3.43x10 7 to 6.86x10 7 pascals will produce strong tablets that break up rapidly. Break-up times are determined by dropping a tablet, typically 5 to 15 g into 1000 mL of water. The "end point" of final dispersion is easy to determine because the tablet floats to the surface as it loses weight shortly before it finally disperses. The resultant dispersion is then poured through a nest of 50/100/200 mesh screens (300 mm, 150 mm, 75 mm holes, respectively). A qualitative judgment is then made about the amount of material that is retained on each screen. A good tablet will leave just a "trace" on the 200 mesh screen, and the larger screens will be free of residue.
• the strength of the tablet can be measured by a tester such as the Erweka ®
• Model TBH 28 The tablet is- stood on end and die machine tip moves to the tablet along an axial path.
• the force to break the tablet in two is normally recorded in newtons (N).
• Good tablets normally have strengths in the range of 8.896x10 3 to 4.448X10 4 N.
• Tekmar ® A-10 analytical laboratory mill The premix was passed through a 50 mesh screen and blended well. A 15 g tablet, 4.34 cm in diameter, was made with a hand-operated hydraulic press at a pressure of 525 kg/cm 2 .
• LomarPWA ® ammonium salt of naphthalene
• Polyplasdone XL- 100 ® polyvinylpolypyrrolidone
• the fresh tablet took 2 min and 23 sec to dissolve in 25°C water with only a trace of solids on die screens.
• a second 15 g tablet was allowed to sit at room temperature for 3 days to allow the water in it to diffuse into the internal desiccant (MgO).
• the tablet was sealed in a tight jar and aged at 45°C for 3 weeks. This accelerated aging simulates about two years of storage at ambient conditions.
• Lomar PWA ® ammonium salt of naphthalene
• the fresh tablet took 2 min and 50 s to break-up in 25°C water. There was only a trace of solids on the screens.
• the second tablet was aged as in Example 1. After aging, the tablet took 2 min and 51 s to break-up. There was only a trace of solids on the wet screens.
• tablets can be prepared using the active ingredients in the first column of Table 2 with one or more of the desiccants listed in the second and third columns, except that when the base employed is potassium carbonate or bicarbonate, the desiccant(s) employed therewith are to be selected solely from Column A.
• tablet formulations can be made whereby the active ingredient pesticide is as described hereafter and the delivery system with its characteristic internal desiccant is as defined herein.
• the pesticide described in more detail in U.S. 4,127,405, is a compound of the formula:
• R 3 and R 6 are independendy hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH 3 S(O) n - or CH 3 CH 2 S(O) n -;
• R 4 is hydrogen, fluorine, chlorine, bromine or methyl
• R 5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy
• R 7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atoms;
• R 8 is hydrogen, methyl, chlorine or bromine
• R 9 and R 10 are independently hydrogen, methyl, chlorine or bromine; W and Q are independently oxygen or sulfur;
• n 0, 1 or 2;
• X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH 3 S- or CH 3 OCH 2 -;
• Z is methyl or methoxy, or their agriculturally suitable salts.
• the pesticide described in more detail in U.S. 4,394,506, is a compound of the formula:
• N-(heterocyclicaminocarbonyl)arylsulfonamides in which the aryl radical is substituted in the 2-position by a carboxy radical, ester, thioester, or amide thereof; e.g., N-[(4,6-dimethylpyrimidin-2yl)aminocarbonyl]- methoxycarbonyl]benzenesulfonamide or N-[(4,6-dimethoxy-1,3,5- triazin-2-yl)amino-carbonyl]-2-methoxycarbonylbenzenesulfonamide.
• the pesticide described in more detail in U.S. 4,481,029, is a compound of the formula:
• W' is O or S
• A' is H, Cl, Br, C 1 -C 4 alkyl, OCH 3 , ⁇ O 2 or CF 3 ;
• A is -C-Q-R I or -C-R II
• Q is O, S or -N-;
• R III is H, C 1 -C 4 alkyl or C 3 -C 4 alkenyl; when Q is O or S then
• R I is C 1 -C 6 alkyl C 3 -C 6 alkenyl; C 3 -C 6 alkynyl; C 2 -C 6 alkyl substituted with 1-3 Cl, F or Br, or one of CN or OCH 3 ; C 3 -C 6 alkenyl substituted with 1-3 Cl; C 3 -C 6 alkynyl substituted with Cl; C 5 -C 6 cycloalkyl; cyclohexenyl; cyclohexyl substituted with 1-3 CH 3 ;
• R 7 and R 8 are independently H, Cl, CH 3 or OCH 3 ;
• n 0 or 1 ;
• R 9 is H or CH 3 ;
• Z is N, CH or C-F
• X H, Cl, -CH 3 , -OCH 3 or -OCH 2 CH 3 ;
• Y H, Cl, C 1 -C 4 substituted alkyl
• R I and R II are less than 5 carbons
• X 1 H, Cl, OCH 3 , OCH 2 CH 3 or CH 3 ;
• the pesticide described in more detail in U.S.4,435,205, is a compound of the formula:
• W is O or S
• Q is O or NR 5 ;
• R 1 is C 1 -C 4 alkyl, C 1 -C 4 alkyl substimted with 1-3 atoms of F, Cl or Br, CH 2 CH 2 OCH 3 , CH 2 CH 2 CH 2 OCH 3 or
• R 2 is H, F, Cl, Br, OCH 3 , NO 2 , CF 3 or C 1 -C 2 alkyl;
• R 3 is H, F, Cl, Br orCH 3 ;
• R 4 is H, CH 3 or OCH 3 ;
• R 5 is C 1 -C 4 alkyl
• R 6 and R 7 are independently H, F, Cl, Br, CH 3 , CF 3 , NO 2 or OCH 3 ;
• X is NH 2 , N(CH 3 ) 2 , NHCH 3 , C 1 -C 4 alkyl, C 1 -C 4 alkyl substimted with 1-3 atoms of F, Cl or Br, CH 2 OCH 3 , CH 2 OCH 2 CH 3 , C 1 -C 4 alkoxy, C 1 -C 2 alkylthio, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, OCH 2 CH 2 OCH 3 or C 2 -C 4 alkoxy substimted with 1-3 atoms of F, Cl or Br;
• n 1 or 2;
• Y is H, CH 3 , OCH 3 or Cl
• X 1 is O or CH 2 ;
• Y 1 is H, CH 3 , OCH 3 or Cl;
• X 2 and Y 2 are independently CH 3 or OCH 3 ;
• Z is CH, N, CCH 3 , CBr, CCl, CF, Cl, CC 2 H 5 , CCH 2 CH 2 Cl or
• the pesticide described in more detail in U.S. 4,420,325, is a compound of the formula:
• R 1 is F, Cl, Br, CF 3 , C 1 -C 3 alkoxy, C 1 -C 3 alkyl, NO 2 , CO 2 R 4 , SO 2 R 5 ,
• R 2 is H, Cl, Br, F, CF 3 or OCH 3 ;
• R 5 is C 1 -C 3 alkyl or CF 3 ;
• R 6 and R 7 are independendy C 1 -C 3 alkyl
• R 8 is H or CH 3 ;
• R 9 is H or C 1 -C 3 alkyl
• W is O or S
• X is CH 3 , OCH 3 or Cl
• Y is CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , CH 2 OCH 3 , NH 2 , NHCH 3 or N(CH 3 ) 2 ;
• Z is CH or N
• X 1 is H, Cl, CH 3 , OCH 3 or OC 2 H 5 ;
• X 2 is CH 3 , C 2 H 5 , OCH 3 or OC 2 H 5 ;
• X 3 is CH 3 or OCH 3 ;
• Y 1 is CH 3 or OCH 3 ; and dieir agriculturally suitable salts.
• the pesticide described in more detail in U.S. 4,514,211, is a compound of the formula:
• Q is O, S, SO or SO 2 ;
• Q 1 is O, S or SO 2 ;
• L is SO 2 NHCNA
• R 1 is H or C 2 -C 4 alkyl
• R 2 is H or C 1 -C 4 alkyl
• R 3 is H or CH 3 ;
• R 4 is H, Cl, CH 3 , CF 3 , OCH 3 , Br, F, SCH 3 or OCF 2 H;
• R 5 is H, CH 3 , OCH 3 , Cl, Br, NO 2 , CO 2 R 7 , SO 2 R 8 , OSO 2 R 9 ,
• R 6 is H, CH 3 , Cl or Br
• R 8 is C 1 -C 3 alkyl
• R 9 is C 1 -C 3 alkyl or CF 3 ;
• R 10 and R 11 are independentiy C 1 -C 2 alkyl
• R 12 is H or CH 3 ;
• W is O or S
• X is H, CH 3 , OCH 3 , Cl. F. OCF 2 H or SCF 2 H;
• Y is CH 3 , OCH 3 , OC 2 H 5 , CH 2 OCH 3 , ⁇ H 2 , NHCH 3 , N(CH 3 ) 2 ,
• CH(OCH 3 ) 2 , CH(OCH 2 CH 3 ) 2 , C 2 H 5 , CF 3 , CH 2 CHCH 2 O, CH ⁇ CCH 2 O, CF 3 CH 2 O, OCH 2 CH 2 Cl, OCH 2 CH 2 Br, OCH 2 CH 2 F, CN, CH 2 OCH 2 CH 3 , OCH 2 CH 2 OCH 3 or GCF 2 T wherein G is O or S and T is H, CHClF, CHBrF, CF 2 H or CHFCF 3 ;
• Z is CH, N, CCH 3 , CC 2 H 5 , CCl or CBr;
• Y 1 is O or CH 2 ;
• X 1 is CH 3 , OCH 3 , OC 2 H 5 or OCF 2 H;
• X 2 is CH 3 , C 2 H 5 or CH 2 CF 3 ;
• Y 2 is C 2 H 5 , CH 3 , OCH 3 , OC 2 H 5 , SCH 3 or SC 2 H 5 ;
• X 3 is CH 3 or OCH 3 .
• the pesticide described in more detail in U.S. 4,547,215, is a compound of the formula:
• R is C 2 H 5 or CH(CH 3 ) 2 ;
• the pesticide described in more detail in U.S. 4,548,638, is a compound of the formula:
• the pesticide described in more detail in U.S. 4,479,821, is a compound of the formula:
• A is a C 1 -C 6 alkyl radical which is substituted by C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl;
• X is oxygen, sulfur, a sulfinyl or sulfonyl bridge
• Z is oxygen or sulfur
• n 1 or 2;
• R 2 is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 1 -C 4 haloalkyl, or a radical -Y-R 5 , -COOR 6 , -NO 2 or -CO-NR 7 R 8 ;
• R 3 and R 4 are hydrogen, C 1 -C 4 alkyl,
• R 5 and R 6 are C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl;
• R 7 and R 8 are hydrogen, C 1 -C 5 alkyl
• Y is oxygen, sulfur, a sulfinyl or sulfonyl bridge, and salts of these
• the pesticide described in more detail in U.S. 4,566,898, is a compound of the formula:
• the pesticide described in more detail in U.S. 4,435,206, is a compound of the formula:
• R 1 is H, Cl, Br, F, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, NO 2 , CF 3 , COOR 5 or SO 2 NR 6 R 7 ;
• R 2 is H, Cl, Br or CH 3 ;
• R 3 and R 4 are independendy H or CH 3 ;
• R 5 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 OCH 2 CH 3 ,
• R 6 and R 7 are independently CH 3 or CH 3 CH 2 ;
• W is oxygen or sulfur
• X is CH 3 -OCH 3 or -OCH 2 CH 3 ;
• Y is H, Cl, CH 3 , CF 3 , -NHCH 3 , -N(CH 3 ) 2 -, -CH 2 OR 8 , -CH 2 CH 2 OR 8 ,
• Z is CH or ⁇
• N oxygen or sulfur
• R 8 is CH 3 , CH 3 CH 2 -, CH 2 CO 2 R 8 , -CH 2 CH 2 OR 6 , C(CH 3 )HCO 2 R 8 or
• Y 1 is H, CH 3 or OCH 3 ; and X 1 is H, Cl, -OCH 3 , -OCH 2 CH 3 or CH 3 ;
• the pesticide described in more detail in U.S.4,514,212, is a compound of the formula:
• Q is fluorine, fluoromethyl, chloromethyl, trichloromethyl, 1,2-dichloro- ethyl, 1,2-dibromoemyI, 1,2-dichloropropyl, 1,2-dibromopropyl, 1,2-dibromoisobutyl, 1,2-dichloro-1-methyl-ethyl or 1,2-dibromo- 1-methylethyl;
• X is oxygen, sulfur, a sulfinyl or sulfonyl bridge
• Z is oxygen or sulfur
• R 2 is hydrogen, halogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 1 -C 4 haloalkyl, or a radical -Y-R 5 , -COOR 6 , -NO 2 or -CO-NR 7 -R 8 ;
• R 3 and R 4 are hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, halogen or alkoxyalkyl of at most 4 carbon atoms;
• R 5 and R 6 are C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl;
• R 7 and R 8 are hydrogen, C 1 -C 5 alkyl, C 2 -C 5 alkenyl or C 2 -C 6 alkynyl;
• Y is oxygen, sulfur, a sulfinyl or sulfonyl bridge.
• the pesticide described in more detail in U.S.4,478,635, is a compound ofie formula:
• X is a radical of the formula:
• Y is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 2 -C 3 alkoxyalkyl, C 1 -C 3 alkylthio, halogen or -NR 16 R 17 ;
• Z is oxygen or sulfur
• R 1 is hydrogen, halogen, cyano, nitro, C 1 -C 4 haloalkyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, -CO-R 6 , -NR 7 R 8 , -S(O) m -C 1 -C 4 alkyl or -SO 2 R 9 ;
• R 2 is hydrogen, fluorine, chlorine, bromine, nitro, trifluoromethyl,
• R 21 methyl, ethyl, methoxy, ethoxy or -S(O) m -C 1 -C 4 alkyl;
• R 3 is hydrogen, fluorine, chlorine, bromine, amino, nitro or methoxy;
• R 6 is hydrogen, C 1 -C 4 alkyl, C 1 -C 3 alkenyloxy, C 3 -C 5 alkynyloxy, C 1 -C 4 haloalkyl, C 1 -C 5 alkylthio, phenoxy, benzyloxy, -NR 10 R 11 or C 1 -C 5 alkoxy which is unsubstituted or substimted by 1 to 3 halogen atoms or C 1 -C 3 alkoxy;
• R 7 is hydrogen, methoxy, ethoxy, C 1 -C 4 alkyl or -CO-R 12 ;
• R 8 is hydrogen or -CO-R 12 ;
• R 9 is an -O-R 13 or -NR 14 R 15 group
• R 11 is C 1 -C 4 alkyl which is unsubstituted or substimted by 1 to 3 halogen atoms, or is phenyl or benzyl;
• R 12 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy
• R 4 has the same meaning as R 2 ;
• R 5 has die same meaning as R 1 ;
• R 10 , R 11 , R 14 and R 20 each have the same meaning as R 7 ;
• R 12 ,R 15 , R 16 , R 17 and R 21 each have die same meaning as R 8 .
• the pesticide described in more detail in U.S. 4,634,465, is a compound of the formula:
• Z is oxygen or sulfur
• R 1 is hydrogen, halogen, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4
• alkoxy C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl or C 2 -C 5 alkoxyalkoxy;
• R 2 is hydrogen, C 1 -C 4 alkyl or C 1 -C 3 alkoxy
• R 3 and R 4 are hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylthio, halogen, C 2 -C 5 alkoxyalkyl, C 2 -C 5 alkoxyalkoxy or -NR 5 R 6 , wherein R 5 and R 4 are hydrogen or C 1 -C 4 alkyl; and
• A is an unsubstimted or substimted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and, together with die linking carbon atom, forms a non-aromatic 5- or 6-membered heterocyclic ring system, with die proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the -SO- or -SO 2 - group.
• the pesticide described in more detail in EPA-202,830, is:
• the pesticide described in more detail in EPA-237,292, is a compound of the formula:
• R is H or CH 3 ;
• R 1 is H or C 1 -C 3 alkyl
• R 2 is C 1 -C 3 alkyl or C 1 -C 2 alkoxy
• R 1 and R 2 may be taken together to form -(CH 2 ) n -, wherein n is 2, 3 or 4;
• R 3 is H, Cl, F, Br, CH 3 , CF 3 , OCH 3 or COF 2 H;
• X is CH 3 , CH 2 F, CH 2 CH 3 , OCH 3 , OCH 2 CH 3 , Cl, OCF 2 H or CH 2 OCH 3 .
• the pesticide described in more detail in EPA-87,780, is a compound of the formula: wherein
• A represents a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group which may be substituted with C 1 -C 8 alkyl groups, halogen atoms or nitro groups;
• B and C represent independendy hydrogen atoms, halogen atoms, mtro groups, C 1 -C 8 alkyl groups, arylalkyl groups, C 1 -C 8 alkoxy groups; haloalkyl groups, -CO 2 R [where R is a hydrogen atom, a C 1 -C 8 alkyl group, an allyl group or a propargyl group), -CONR 1 R 2 (where R 1 is a hydrogen atom, a C 1 -C 8 alkyl group or a phenyl group, R 2 is a hydrogen atom or a C 1 -C 8 alkyl group, or R 1 and R 2 taken togedier may represent -(CH 2 ) m - (m is 4, 5
• R 7 each represent hydrogen atoms or C 1 -C 8 alkyl groups) or either X or Y may form a five-membered ring containing an oxygen atom together with X; and X represents a nitrogen atom or C-R 8
• R 8 represents a hydrogen atom, a haloalkyl group or may form a five -membered ring containing an oxygen atom together with X or Y).
• the pesticide described in more detail in U.S. 4,710,221, is a compound of the formula:
• R is H or CH 3 ;
• R 1 is C 1 -C 3 alkyl, C 3 -C 4 alkoxyalkyl, C 2 -C 4 haloalkyl, C 3 -C 4 alkenyl or
• R 2 is C 2 -C 6 alkoxy, C 3 -C 6 cycloalkoxy, C 4 -C 6 cycloalkylalkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -C 4 alkoxyalkoxy, C 2 -C 4 haloalkoxy alkoxy, C 2 -C 4 alkylthioalkoxy, C 2 -C 4 haloalkylthio- alkoxy, C 2 -C 4 alkylsulfinylalkoxy, C 2 -C 4 haloalkylsulfinylalkoxy, C 2 -C 4 alkylsulfonylalkoxy, C 2 -C 4 haloalkylsulfonylalk
• OSi(CH 3 ) 3 OSi(CH 3 ) 2 C(CH 3 ) 3 , C 1 -C 4 alkylthio, C 3 -C 4 cycloalkylthio, cyclopropylmethyldiio, C 1 -C 4 haloalkyldiio, C 2 -C 4 alkenylthio, C 2 -C 4 haloalkenylthio, C 3 -C 4 alkynyltiiio, C 3 -C 4 haloalkynylthio, C 2 -C 4 alkoxy alkylthio, C 2 -C 4 aminoalkyltiiio, SH, SP(O)(OC 1 -C 2 alkyl) 2 , C 1 -C 4 alkylsulfinyl, C 3 -C 4 cycloalkylsulfonyl, cyclopropylmediylsulfinyl, C 1 -C 4 cycl
• alkoxyalkylsulfinyl C 2 -C 4 aminoalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 3 -C 4 cycloalkylsulfonyl, cyclopropylmediylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 haloalkenylsulfonyl,
• R a and R b are independendy H or C 1 -C 3 alkyl
• R c is C 2 -C 4 alkyl, cyclopropylmethyl, C 2 -C 4 cyanoalkyl, CH 2 C(O)CH 3 , CH 2 CH 2 C(O)CH 3 , C 10 -C 4 haloalkyl, C 3 -C 4 alkenyl, C 3 -C 4 haloalkenyl, C 3 -C 4 alkynyl, C 3 -C 4 haloalkynyl, C 1 -C 4 alkyl substimted widi C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, OH, NH 2 , NHCH 3 or N(CH 3 ) 2 ;
• X is CH 3 , OCH 3 , OC 2 H 5 , Cl or Br;
• Y is C 1 -C 2 alkyl, C 1 -C 2 alkoxy, OCH 2 CH 2 F, OCH 2 CHF 2 , OCH 2 CF 3 ,
• Z is CH or N

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• 1992
  • 1992-12-30 AU AU34261/93A patent/AU668706B2/en not_active Ceased
  • 1992-12-30 HU HU9402031A patent/HUT68006A/hu unknown
  • 1992-12-30 WO PCT/US1992/011305 patent/WO1993013658A1/en not_active Application Discontinuation
  • 1992-12-30 BR BR9207062A patent/BR9207062A/pt not_active Application Discontinuation
  • 1992-12-30 CA CA 2127093 patent/CA2127093A1/en not_active Abandoned
  • 1992-12-30 JP JP5512485A patent/JPH07502745A/ja active Pending
  • 1992-12-30 EP EP93902823A patent/EP0620706A1/en not_active Withdrawn
• 1993
  • 1993-01-04 TR TR00015/93A patent/TR28073A/xx unknown
  • 1993-01-06 CN CN 93100808 patent/CN1074083A/zh active Pending
• 1994
  • 1994-07-05 FI FI943206A patent/FI943206A/fi unknown

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