WO1995031448A1 - Pesticides de n-(5-isothiazolyle)amide - Google Patents

Pesticides de n-(5-isothiazolyle)amide Download PDF

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Publication number
WO1995031448A1
WO1995031448A1 PCT/US1995/006307 US9506307W WO9531448A1 WO 1995031448 A1 WO1995031448 A1 WO 1995031448A1 US 9506307 W US9506307 W US 9506307W WO 9531448 A1 WO9531448 A1 WO 9531448A1
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Prior art keywords
alkyl
halo
phenyl
substituted
formula
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PCT/US1995/006307
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English (en)
Inventor
Ronald E. Hackler
George W. Johnson
Jack G. Samarintoni
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Dowelanco
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Priority to AU26412/95A priority Critical patent/AU2641295A/en
Priority to JP7529898A priority patent/JPH10503171A/ja
Publication of WO1995031448A1 publication Critical patent/WO1995031448A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • This invention relates to novel N-(5-isothiazolyl)amide compounds useful as nematicides, insecticides, miticides, and plant fungicides.
  • the present invention also provides nematicidal,
  • insecticidal miticidal, and fungicidal methods.
  • nematicides typically have high mammalian toxicity and must be used at high rates.
  • a nematicide that can be applied at lower rates and that has lower mammalian toxicity would represent a significant advance.
  • Mites and insects are developing resistance to the miticides and insecticides in current use. Resistance to insecticides in anthropods is widespread, with at least 400 species resistant to one or more
  • fungicides At least 50 species of fungi have developed resistance to the benzimidazole fungicides. Even recently introduced fungicides, like the acylalanines, which initially exhibited excellent control of potato late blight and grape downy mildew in the field, have become less effective because of resistance. Therefore a need exists for new
  • insecticides insecticides, miticides, and fungicides, and particularly for compounds that have new or atypical modes of action.
  • This invention provides compounds represented by Formula (1), (2), and (3), below:
  • R and R 1 are each independently independently H, (C1-C4) alkyl, (C1-C4) alkyl optionally substituted with CH 2 CH(OCH 3 ) 2 , halo, (C1-C4) alkoxy, or , wherein B is O or NR 1 and n is an integer
  • E is H, (C1-C4) alkyl, or a cation, such as, for example, sodium, potassium, or ammonium; trifluoroacetyl; alkoxymethyl; hydroxymethyl; formyl; (R 2 )2NS(O) x ; benzyl; or benzyl optionally substituted with (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halo, halo (C 1 -C 4 ) alkyl;
  • Each R 2 is independently lower alkyl, aryl, or together form with nitrogen a saturated (C 3 -C 7 ) ring such as morpholino, piperidinyl, pyrrolidinyl;
  • x is an integer from 0 to 2;
  • R 3 and R 4 are each independently H, (C 1 -C 4 ) alkyl, halogen, I, (C 1 -C 4 ) alkoxy, halo (C 1 -
  • unsaturated hydrocarbon chain straight chain or branched, optionally including a hetero atom selected from O, NR 5 , S, SO, SO 2 , or SiR 6 R 7 , and optionally substituted with one or more groups independently selected from (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, branched (C 3 -C 7 ) alkyl, (C 3 -C 7 ) cycloalkyl, (C 3 -C 7 ) cycloalkenyl, halo, halo (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy, hydroxy, or (C 1 -C 4 ) acyl; R 5 is H, (C 1 -C 4 ) alkyl, or (C 1 -C 4 ) acyl;
  • hydrocarbon radical one to five carbon atoms long optionally substituted with (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, branched (C 3 -C 7 ) alkyl, (C 3 -C 7 ) cycloalkyl, (C 3 -C 7 ) cycloalkenyl, halo, halo (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy, hydroxy, CN, (C 1 -C 4 ) acyl, (C 1 -C 4 ) alkoxycarbonyl, aryloxycarbonyl, hydroxy (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, methylene, methylene optionally substituted with one or more groups independently selected from hydrogen; (C 1 -C 4
  • aryl (a) aryl or (b) (C 3 -C 8 ) cycloalkyl or cycloalkenyl, optionally substituted with one or more groups independently selected from (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halo (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy, halo, hydroxy, or (C 1 -C 4 ) acyl; where aryl is
  • R 8 is (C 1 -C 7 ) alkyl, halo (C 1 - C 7 ) alkyl, (C 3 -C 7 ) branched alkyl, halo (C 3 -C 7 ) branched alkyl, (C 3 -C 7 ) cycloalkyl, halo (C 3 -C 7 ) cycloalkyl, (C 1 -C 7 ) alkoxy, hydroxy, phenyl, substituted phenyl, phenoxy, or substituted phenoxy, , wherein R 8 cannot be hydroxy,
  • SiR 9 R 10 R 11 or OSiR 9 R 10 R 11 where R 9 ,R 10 and R 11 are independently (C 1 -C 4 ) alkyl, (C 3 -C 4 ) branched alkyl, phenyl, or substituted phenyl,
  • R 12 and R 13 are independently H, (C 1 -C 4 ) alkyl, or (C 1 -C 4 ) acyl, S(O)R 14 , SO 2 R 14 , or OSO 2 R 14 , where R 14 is
  • hydrocarbon chain straight chain or branched optionally including a hetero atom selected from O, S, SO, SO 2 , NR 5 , or SiR 6 R 7 , where R 5 , R 6 and R 7 are as defined above, and optionally substituted with halo, halo (C 1 -C 4 ) alkoxy, hydroxy, (C 3 -C 8 ) cycloalkyl or cycloalkenyl, (C 1 -C 4 ) acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio, substituted phenylthio, or cyano;
  • R 15 is H, halo, halomethyl, CN, NO 2 , (C 1 -C 4 ) alkyl, (C 3 -C 4 ) branched alkyl, phenyl, (C 1 -C 4 ) alkoxy; (c) a thienyl group of the formula (4)
  • R 16 is H, halo, halomethyl, CN, NO 2 , (C 1 -C 4 ) alkyl, (C 3 -C 4 ) branched alkyl, phenyl, (C 1 -C 4 ) alkoxy, or thienyl; (d) a group of formula (5) or (6)
  • R 15 is as defined in paragraph (b), J is N or CH, and G is O, NR 17 , or S, provided that if J is not N then G is NR, where R 17 is H, ( C1 -C 4 ) alkyl, (C 1 -C 4 ) acyl, phenylsulfonyl, or substituted phenylsulfonyl;
  • R 20 are independently H, halo, lower alkyl, lower alkoxy, haloalkyl, haloalkoxy, NO 2 , CN, lower alkyl carbonyl, phenoxy, or substituted phenoxy, provided that at least two of R 20 are selected from H and F; and Het is pyridinyl, pyrazinyl, pyrimidinyl, or pyridazinyl, optionally substituted with one or more groups selected from halo, lower alkyl, lower alkoxy, haloalkyl, haloalkoxy, NO 2 , CN, and lower alkyl carbonyl;
  • R 21 is -T-R 22 , phenyl, substituted phenyl, (C 1 -C 10 ) alkyl, halo, or halo (C 1 -C 8 ) alkyl, where
  • T O or S
  • R 22 is (C 1 -C 4 ) alkyl, (C 3 -C 7 ) branched alkyl, halo (C 1 -C 7 ) alkyl, halo (C 3 -C 7 ) branched alkyl, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, or naphthyl or phenyl, either of which may be optionally substituted with up to three groups selected from halo, (C 1 -C 10 ) alkyl, branched (C 3 -C 7 ) alkyl, halo (C 1 -C 7 ) alkyl, hydroxy (C 1 -C 7 ) alkyl, (C 1 -C 4 ) alkoxy, halo (C 1 -C 4 ) alkoxy, phenoxy, substituted phenoxy, phenyl, substituted phenyl, CN, NO 2 , OH, (C 1 -C 4 )
  • R 8 is (C 1 -C 7 ) alkyl, halo (C 1 -C 7 ) alkyl, (C 3 -C 7 ) branched alkyl, halo (C 3 -C 7 ) branched alkyl, (C 3 -C 7 ) cycloalkyl, halo (C 3 -C 7 ) cycloalkyl, (C 1 -C 7 ) alkoxy, phenyl, substituted phenyl, or hydroxy, acetoxy, OH,
  • SiR 9 R 10 R 11 or OSiR 9 R 10 R 11 where R 9 ,R 10 and R 11 are independently (C 1 -C 4 ) alkyl, (C 3 -C 4 ) branched alkyl, phenyl, or substituted phenyl,
  • R 12 and R 13 are independently H, (C 1 -C 4 ) alkyl, or (C 1 -C 4 ) acyl,
  • R 14 is (C 1 -C 10 ) alkyl, phenyl, or substituted phenyl; a (C 1 -C 12 ) saturated or unsaturated
  • hydrocarbon chain straight chain or branched optionally including a hetero atom selected from O, S, SO, SO 2 , NR 5 , or SiR 6 R 7 , where R 5 , R 6 and R 7 are as defined above, and optionally substituted with halo, halo (C 1 -C 4 ) alkoxy, hydroxy, (C 3 -C 8 ) cycloalkyl or cycloalkenyl, (C 1 -C 4 ) acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio, substituted phenylthio, or cyano; (C 1 -C 7 ) alkoxy optionally substituted with halo, phenyl, substituted phenyl, (C 3 -C 8 )
  • W is O, S(O) y , wherein y is an integer from 0 to 2, or NR 24 ;
  • G is (C 1 -C 4 ) alkyl, aryl, (C 1 -C 4 ) acyl, NR 25 R 26 , deuterio (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkyl, benzyl, or benzyl optionally substituted with (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halo, halo (C 1 -C 4 ) alkyl; or
  • W-G together are halo, SH, or NR 25 R 26 ;
  • R 24 is H, OH, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, aryl,
  • R 25 and R 26 are independently H, (C 1 -C 4 ) alkyl, aryl, acyl, or together form with nitrogen a saturated (C 3 -C 7 ) ring such as morpholino, piperidinyl,
  • the invention also provides a method of inhibiting a nematode population which comprises applying to the locus of a nematode, a nematode inactivating amount of a compound of the Formula (1), (2), or (3) as defined above.
  • the invention also provides a method of inhibiting an insect or mite population which comprises applying to the locus of the insect or arachnid an effective insect or mite inactivating amount of a compound of Formula (1), (2), or (3).
  • the invention also provides a method of inhibiting plant pathogens which comprises applying an effective amount of a compound of Formula (1), (2), or (33 to a locus of the pathogen.
  • halo or halogen refers to a F, CI, or Br atom.
  • alkyl refers to straight chain and branched chain groups.
  • aryl refers to such groups wherein the phenyl ring is substituted with up to three groups independently selected from halo, I, (C 1 -C 10 ) alkyl, branched (C 3 -C 6 ) alkyl, halo (C 1 -C 7 ) alkyl, hydroxy (C 1 -C 7 ) alkyl, (C 1 -C 7 ) alkoxy, halo (C 1 -C 7 ) alkoxy, phenoxy, substituted phenoxy, phenyl,
  • substituted naphthyl and “substituted indolyl” refer to these ring systems substituted with one or more groups independently selected from halo, halo (C 1 -C 4 ) alkyl, CN, NO 2 , (C 1 -C 4 ) alkyl, (C 3 -C 4 ) branched alkyl, phenyl, (C 1 -C 4 ) alkoxy, or halo (C 1 -C 4 ) alkoxy.
  • carbocyclic ring refers to a saturated or unsaturated carbocyclic ring containing five or six carbon atoms.
  • saturated hydrocarbon chain refers to a hydrocarbon chain containing one or more sites of unsaturation.
  • HPLC refers to a high pressure liquid chromatography.
  • TLC thin layer
  • bivalent hydrocarbon radical refers to bivalent radicals derived from normal alkanes by removal of hydrogen atoms from each of the two terminal carbon atoms of the chain, e.g. methylene, ethylene, trimethylene, tetramethylene, etc.
  • substituted amino refers to an amino group that is substituted with one or two (C 1 -C 4 ) alkyl groups or one (C 1 -C 4 ) alkanoyl group.
  • lower alkyl refers to (C 1 -C 6 ) straight hydrocarbon chains and (C 3 -C 6 ) branched and cyclic hydrocarbon groups.
  • lower alkenyl and lower alkynyl refer to (C 2 -C 6 ) straight hydrocarbon chains and (C 3 -C 6 ) branched hydrocarbon groups containing at least one unsaturated bond.
  • lower alkoxy and “lower alkylthio” refer to O-lower alkyl and S-lower alkyl groups.
  • haloalkyl refers to lower alkyl groups substituted with one or more halo atoms.
  • deuterioalkyl refers to lower alkyl groups substituted with one or more deuterium atoms.
  • Preferred compounds of Formula (1), (2), or (3) include the following classes: (a) compounds of Formula (1), (2), or (3) wherein Y is CH2;
  • the acid derivative (6) is mixed with an excess molar amount of thionyl chloride and the resulting mixture is heated at reflux for approximately one to three hours to yield the acid chloride derivative (5).
  • the amine derivative (4) is dissolved in a sufficient quantity of an organic solvent, such as, for example xylene or toluene, with heating.
  • the acid chloride (5) is added with continued heating for one to twelve hours, then the resulting mixture is allowed to cool. Separation utilizing standard techniques yields the desired compounds of Formula (1).
  • the above compounds of Formula (1) and (3) are obtained by treatment of the carbonyl derviative (A) in the presence of a phase transfer reagent, such as, for example, benzyl triethylammonium bromide, a base, such as, for example, sodium hydroxide, in amthylene chloride/water mixture.
  • a phase transfer reagent such as, for example, benzyl triethylammonium bromide
  • a base such as, for example, sodium hydroxide
  • the above compounds of formula (1) and (3) can also be obtained by heating the amide A with a dialkyl sulfate in the presence of potassium carbonate in a inert solvent such as, for example, benzene.
  • the above compounds of Formula (1) and (3) can also be obtained under non-aqueous conditions using sodium or potassium hydride and alkyl halide in an aprotic solvent such as, for example, ethyl ether or tetrahydrofuran.
  • an aprotic solvent such as, for example, ethyl ether or tetrahydrofuran.
  • Methylene derivatives (3) wherein the methylene is substituted with N(CH 3 ) 2 may be prepared by treating the N-(5-isothiazolyl)amide (10) with the appropriate N ,N-dialkyIcarboxamide di-alkylacetal in the presence of toluene with heating.
  • the N,N-dialkyl derivatives (11) can be converted to their NHR 24 derivatives by treating with the appropriate amine to give (12).
  • the N-(5-isothiazolyl)amides (10) can also be converted to S,S-ketene acetals (14) and optionally, to cyclic systems (15).
  • the carbonyl derivative (1) is treated with
  • Lawesson's reagent to give the thione (9) which can be converted to amidines where W-G NR 25 R 26 or NHR 25 with primary and secondary amines.
  • the starting acid (28.2 g, 0.187 mole) was added to H 2 O (200 ml).
  • the insolubles were filtered and the filtrate's pH was adjusted to 10.0 with the addition of 2N NaOH (94 ml).
  • the mixture was stirred for five minutes, then extracted with ethyl ether (1 ⁇ 230 ml).
  • the organic layer was separated and the aqueous layer was saturated with NaCl, then extracted with ethyl ether (2 ⁇ 230 ml).
  • the extracts were combined and given a brine wash, dried over MgSO 4 , then concentrated under vacuum to give the product as a yellow oil (18.9 g).
  • the starting nitrile (6.0 g) was dissolved in pyridine (20 ml) in a Carius tube. Hydrogen sulfide (2.8 g) was bubbled in. and the resulting mixture was placed in an oven at 120° for five hours. The solvent was removed under vacuum and the resulting mixture was dissolved in CH 2 Cl 2 (250 ml) and washed with water ( ml). Thin layer chromatography showed more extensive reaction and more impurities than material of Example 3. The solvent was removed under vacuum. To the product was added ethanol (100 ml) and 30% H 2 O 2 (20 ml). The resulting mixture became very hot. Water (200 ml) was then added and the mixture was extracted with two portions of CH 2 Cl 2 (2 ⁇ 150 ml).
  • EXAMPLE 5 The starting amine (18.9 g, 0.166 mole) was slurried in CCI 4 (600 ml) under an atmosphere of N2. N-chlorosuccinimide (NCS) (22.1 g, 0.166 mole) was added to the slurry over a five minute period at 30-44° and stirred at room temperature overnight. Analysis by TLC silica gel 1:1 heptane/ethyl acetate showed product and no starting material present. The mixture was then diluted with ethyl ether (100 ml) and the solids were filtered.
  • NCS N-chlorosuccinimide
  • Example 6 To the product of Example 6 was added dry THF (270 ml) and ethanol (200 ml). Of this solution, 70 ml was put in each of two Carius tubes. The tubes were cooled and NH 3 (2.1 g) was added followed by H 2 S (3.0 g). The tubes were sealed and warmed in hot water to check for leaks, then placed in an oven at 110° for four hours, after which the mixture was cooled and the solvent removed under vacuum. To this product was added CH 2 Cl 2 (300 ml) and the mixture was washed with two portions of water (2 ⁇ 100 ml). The mixture was then dried over MgSO4 and the solvent was removed under vacuum.
  • CH 2 Cl 2 300 ml
  • the starting amine (3.7 g, 0.0289 mole) was dissolved in chloroform (100 ml) at room temperature under an atmosphere of N 2 , and the chlorine (2.25 g. 0.0317 mole) was dissolved in chloroform (120 ml).
  • the amine solution was chilled to 15° and the chlorine solution was added dropwise over a 15 minute period at 15°, and a dark precipitate formed.
  • the cooling bath was removed and the solution was heated to 50° for one hour. Heat was removed and saturated sodium
  • the amine (4.0 g, 0.0312 mole) was slurried in CCI 4 (130 ml) at room temperature under an atmosphere of N 2 .
  • the N-chlorosuccinimide (4.25 g, 0.0312 mole) was added portionwise over a 5 minute period at 25-37°, and the mixture was stirred at room temperature for 1.5 hours.
  • Analysis by TLC silica gel (1:1 heptane/ethyl acetate) showed no starting material remaining.
  • the mixture was then diluted with ethyl ether (250 ml) and filtered. The filtrate was washed twice with water.
  • the organic layer was separated and given a brine wash, then dried over MgSO 4 , and concentrated under vacuum to yield a brown oil (4.65 g).
  • the amine 0.73 g, 0.0049 mole was dissolved in warm xylenes (40 ml) and heating was continued in an oil bath wherein the acid chloride (1.26 g, 0.0057 mole), dissolved in xylenes (10 ml), was added to the amine solution dropwise over a five minute period under an atmosphere of N 2 at 80- 100°. A precipitate immediately formed. The slurry was then heated at 140° for one hour and all the precipitate dissolved. The resulting mixture was stirred overnight at room temperature. Analysis by TLC 9:1 CH 2 Cl 2 /ethyl acetate silica gel showed a faint spot remaining for the starting amine. The mixture was then concentrated under vacuum to a tan solid (1.6 g).
  • the starting acid (1.20 g, 0.0051 mole) was slurried in dichloromethane (20 ml) under an atmosphere of N 2 .
  • Thionyl chloride (1 ml, 0.0137 mole) was added and the resulting mixture was heated at reflux
  • the starting acid (1.25 g, 0.0048 mole) was dissolved in thionyl chloride (25 ml) and heated at reflux temperature for two hours, then concentrated under vacuum to give the acid chloride as a yellow oil (1.34 g).
  • the amine (0.80 g, 0.0041 mole) was
  • the compounds of Formula (1), (2), or (3) show activity against a number of insects and mites. More specifically, the compounds show activity against melon aphid, which is a member of the insect order Homoptera .
  • Other members of the Homoptera include leafhoppers, planthoppers, pear pyslla, apple sucker, scale insects, whiteflies, spittle bugs as well as numerous other host specific aphid species. Activity has also been
  • the compounds of Formula (1), (2), or (3) are useful for reducing populations of insects and mites, and are used in a method of inhibiting an insect or mite population which comprises applying to a locus of the insect or mite an effective insect- or
  • insects or mites are a term used herein to refer to the environment in which the insects or mites live or where their eggs are present, including the air surrounding them, the food they eat, or objects which they contact.
  • locus of insects or mites is a term used herein to refer to the environment in which the insects or mites live or where their eggs are present, including the air surrounding them, the food they eat, or objects which they contact.
  • plant-ingesting insects or mites can be controlled by applying the active compound to plant parts, which the insects or mites eat, particularly the foliage. It is contemplated that the compounds might also be useful to protect textiles, paper, stored grain, or seeds by applying an active compound to such substance.
  • the term "inhibiting an insect or mite” refers to a decrease in the numbers of living insects or mites; or a decrease in the number of viable insect or mite eggs. The extent of reduction accomplished by a compound depends, of course, upon the application rate of the compound, the particular compound used, and the target insect or mite species. At least an
  • insect-inactivating or mite-inactivating amount should be used.
  • insect-inactivating amount and “mite-inactivating amount” are used to describe the amount, which is sufficient to cause a measurable reduction in the treated insect or mite population. Generally an amount in the range from about 1 to about 1000 ppm active compound is used.
  • ALH refers to aster leafhopper
  • BAW refers to beet armyworm
  • CA cotton aphid
  • NEM peanut root knot nematode
  • SCRW refers to southern corn root worm
  • TBW refers to tobacco budworm
  • TSSM refers to two spotted spider mite
  • each test compound was formulated as a
  • the 400 ppm solution was prepared by combining 19.2 mL of .05% solution of Tween 20 (polyoxyethylene (20) sorbitan monolaurate) in water with a solution of 8 mg of the compound in 0.8 mL of acetone/EtOH (9/1).
  • leafhoppers were added to each cup.
  • the cups were capped and held at room temperature for 24 hours.
  • a general purpose lepidoptera artificial diet was diluted to half strength with a 5% non nutritive agar. 8 mL of this diet material was dispensed into one ounce diet cups. One hour prior to treatment, 35 to 40 eggs were
  • the cups were then sprayed with formulated material through a flat-fan nozzle. Treated cups were air dried prior to sealing with plastic caps. The cups were held for 6 days at room temperature. Activity was then rated based on the total number of live and dead larvae, and on the size of live larvae.
  • Activity against tobacco budworm was evaluated as follows. A general purpose lepidoptera artificial diet was diluted to half strength with a 5% non nutritive agar. 8 mL of this diet material was dispensed into each one ounce diet cup. One hour prior to treatment 18 to 20 eggs were dispensed onto the diet surface. The cups were then sprayed with formulated material through a flat-fan nozzle. The test was run using concentrations of 400 ppm and 50 ppm. Treated cups were air dried prior to sealing with plastic caps. The cups were held for 6 days at room temperature. Activity was then rated based on the total number of live and dead larvae, and on the size of live larvae.
  • Activity against German cockroach ( Blattella germanicus ) was evaluated as follows. 8 mL of alfalfa based green insect diet material was dispensed into a one ounce diet cup. The cups were then sprayed with formulated material through a flat-fan nozzle. The test was run using concentrations of 400 ppm and 50 ppm. Treated cups were air dried for 24 hours and infested with five late third or early fourth instar German cockroaches. The cups were capped and held for seven days in an environmental growth chamber at a temperature of 76-85°C. Activity was then rated based on the total number of live and dead insects.
  • the compounds of the present invention have been found to control fungi, particularly plant pathogens. When employed in the treatment of plant fungal
  • the compounds are applied to the plants in a disease inhibiting and phytologically acceptable amount.
  • phytologically acceptable amount refers to an amount of a compound of the invention which kills or inhibits the plant disease for which control is desired, but is not significantly toxic to the plant. This amount will generally be from about 1 to 1000 ppm, with 10 to 500 ppm being preferred. The exact concentration of compound required varies with the fungal disease to be controlled, the type
  • a suitable application rate is typically in the range from 0.10 to 4 lb/A.
  • the compounds of the invention may also be used to protect stored grain and other non-plant loci from fungal infestation.
  • test compounds were formulated for application by dissolving 50 mg of the compound into 1.25 ml of solvent.
  • the solvent was prepared by mixing 50 ml of "Tween 20" (polyoxyethylene (20) sorbitan monolaurate emulsifier) with 475 ml of acetone and 475 ml of etha nol.
  • the solvent/compound solution was diluted to 125 ml with deionized water.
  • the resulting formulation contains 400 ppm test chemical. Lower concentrations were obtained by serial dilution with the
  • test compounds were applied by foliar spray.
  • the following plant pathogens and their corresponding plants were employed.
  • Puccinia recondite PUCCRT wheat tritici (leaf rust)
  • the compounds of Formula (1), (2), or (3) may be applied in the form of compositions which are important embodiments of the invention, and which comprise a compound of Formula (1), (2), or (3) and a
  • compositions are either concentrated formulations which are dispersed in water for application, or are dust or granular formulations which are applied without further treatment.
  • the compositions are prepared according to procedures and formulae which are conventional in the agricultural chemical art, but which are novel and important because of the presence therein of the compounds of this invention. Some description of the formulation of the compositions will be given, however, to assure that agricultural chemists can readily prepare any desired composition.
  • the dispersions in which the compounds are applied are most often aqueous suspensions or emulsions prepared from concentrated formulations of the compounds.
  • Such water-soluble, water-suspendable or emulsifiable formulations are either solids usually known as wettable powders, or liquids usually known as emul si fiable concentrates or aqueous suspensions.
  • Wettable powders which may be compacted to form water dispersible granules, comprise an intimate mixture of the active compound, an inert carrier and surfactants.
  • concentration of the active compound is usually from about 10% to about 90% by weight.
  • the inert carrier is usually chosen from among the attapulgite clays, the montmorillonite clays, the diatomaceousearths . or the puri f i ed si l i cat es . Effective
  • surfactan ts co mp ris i ng from about 0 . 5% to about 10% o f the wettable powder, are found among the sulfonated lignins, the condensed naphthalenesulfonates, the naphthalenesulfonates, the alkylbenzenesulfonates, the alkyl sulfates, and non-ionic surfactants such as ethylene oxide adducts of alkyl phenols.
  • Emulsifiable concentrates of the compounds comprise a convenient concentration of a compound, such as from about 50 to about 500 grams per liter of liquid, equivalent to about 5% to about 50%, dissolved in an inert carrier which is either a water miscible solvent or a mixture of water-immiscible organic solvent and emulsifiers.
  • a compound such as from about 50 to about 500 grams per liter of liquid, equivalent to about 5% to about 50%
  • an inert carrier which is either a water miscible solvent or a mixture of water-immiscible organic solvent and emulsifiers.
  • Useful organic solvents include aromatics, especially the xylenes, and the petroleum fractions, especially the high-boiling naphthalenic and olefinic portions of petroleum such as heavy aromatic naphtha.
  • Other organic solvents may also be used, such as the terpenic solvents including rosin derivatives, aliphatic ketones such as
  • Suitable emulsifiers for emulsifiable concentrates are chosen from conventional nonionic surfactants, such as those discussed above.
  • Aqueous suspensions comprise suspensions of water-insoluble compounds of this invention, dispersed in an aqueous vehicle at a concentration in the range from about 5% to about 50% by weight.
  • Suspensions are prepared by finely grinding the compound, and
  • synthetic or natural gums may also be added, to increase the density and viscosity of the aqueous vehicle. It is often most effective to grind and mix the compound at the same time by preparing the aqueous mixture, and homogenizing it in an implement such as a sand mill, ball mill, or piston-type homogenizer.
  • the compounds may also be applied as granular compositions, which are particularly useful for applications to the soil.
  • Granular compositions usually contain from about 0.5% to about 10% by weight of the compound, dispersed in an inert carrier which consists entirely or in large part of clay or a similar inexpensive substance.
  • Such compositions are usually prepared by dissolving the compound in a suitable solvent, and applying it to a granular carrier which has been pre-formed to the appropriate particle size, in the range of from about 0.5 to 3 mm.
  • compositions may also be formulated by making a dough or paste of the carrier and compound, and crushing and drying to obtain the desired granular particle size.
  • Dusts containing the compounds are prepared simply by intimately mixing the compound in powdered form with a suitable dusty agricultural carrier, such as kaolin clay, ground volcanic rock and the like. Dusts can suitably contain from about 1% to about 10% of the compound. It is equally practical, when desirable for any reason, to apply the compound in the form of a solution in an appropriate organic solvent, usually a bland petroleum oil, such as the spray oils, which are widely used in agricultural chemistry. Insecticides and miticides are generally applied in the form of a dispersion of the active ingredient in a liquid carrier. It is conventional to refer to application rates in terms of the concentration of active ingredient in the carrier. The most widely used carrier is water.
  • the compounds of Formula (1), (2), or (3) can also be applied in the form of an aerosol composition.
  • the active compound is dissolved or dispersed in an inert carrier, which is a
  • the aerosol composition is packaged in a container from which the mixture is dispensed through an atomizing valve.
  • Propellant mixtures comprise either low-boiling halocarbons, which may be mixed with organic solvents, or aqueous suspensions pressurized with inert gases or gaseous hydrocarbons.
  • concentrations of from 10 ppm to 5000 ppm of compound are expected to provide good control. With many of the compounds, concentrations of from 100 to 1500 ppm will suffice.
  • a suitable application rate for the compounds is about 0.5 to 1.5 lb/A, typically applied in 50 gal/A of spray formulation containing 1200 to 3600 ppm of compound.
  • a suitable application rate is from about 100 to 1500 gal/A spray formulation, which is a rate of 100 to 1000 ppm.
  • the locus to which a compound is applied can be any locus inhabited by an insect or arachnid, for example, vegetable crops, fruit and nut trees, grape vines, and ornamental plants.
  • an insect or arachnid for example, vegetable crops, fruit and nut trees, grape vines, and ornamental plants.
  • mite species are specific to a particular host, the foregoing list of mite species provides exemplification of the wide range of settings in which the present compounds can be used.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne de nouveaux composés de N-(5-isothiazolyle)amide, présentant les formules (1, 2 ou 3), ainsi que des compositions nématicides, insecticides, acaricides et fongicides. L'invention concerne également des procédés permettant de lutter contre les nématodes, les insectes, les acariens et les champigons.
PCT/US1995/006307 1994-05-17 1995-05-17 Pesticides de n-(5-isothiazolyle)amide WO1995031448A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU26412/95A AU2641295A (en) 1994-05-17 1995-05-17 N-(5-isothiazolyl)amide pesticides
JP7529898A JPH10503171A (ja) 1994-05-17 1995-05-17 Ｎ−（５−イソチアゾリル）アミド有害生物防除剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US24518494A 1994-05-17 1994-05-17
US08/245,184 1994-05-17

Publications (1)

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WO1995031448A1 true WO1995031448A1 (fr) 1995-11-23

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JP (1) JPH10503171A (fr)
AU (1) AU2641295A (fr)
CA (1) CA2189573A1 (fr)
WO (1) WO1995031448A1 (fr)

Cited By (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997018198A1 (fr) * 1995-11-14 1997-05-22 Bayer Aktiengesellschaft 5-aminoisothiazoles acyles avec effet insecticide, produits intermediaires et procede de production correspondant
WO1998002424A1 (fr) * 1996-07-16 1998-01-22 Bayer Aktiengesellschaft N-(5-isothiazolyl)-thioamides substitues
WO1998005670A1 (fr) * 1996-07-31 1998-02-12 Bayer Aktiengesellschaft N-isothiazolyl-(thio)amides substitues
WO1999000375A1 (fr) * 1997-06-26 1999-01-07 Bayer Aktiengesellschaft Aminoheterocyclylamides substitues
WO1999010334A1 (fr) * 1997-08-22 1999-03-04 Bayer Aktiengesellschaft 5-aminoisothiazoles acyles a usage de pesticides et de fungicides
WO2000006566A1 (fr) * 1998-07-30 2000-02-10 Syngenta Limited Derives de benzoxazole, benzthiazole et benzimidazole
WO2000020415A1 (fr) * 1998-10-06 2000-04-13 Bayer Aktiengesellschaft Heterocyclylamides d'acide phenylacetique ayant un effet insecticide
WO2000063207A1 (fr) * 1999-04-20 2000-10-26 Syngenta Limited Derives indazole ou benzotriazole pesticides
WO2000068214A1 (fr) * 1999-05-10 2000-11-16 Syngenta Limited Procede de preparation de composes 5-amino-3-alkylisothiazole et de composes 5-amino-4-chloro-3-alkylisothiazole
WO2001036415A1 (fr) * 1999-11-18 2001-05-25 Novartis Ag Composes pesticides aminoheterocyclamide
WO2001055137A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine et leur utilisation comme pesticides
WO2001055145A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine en tant que pesticides
WO2001055141A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine comme pesticides
WO2001055142A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'isothiazole et leur utilisation comme pesticides
WO2001055140A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'isothiazole et utilisation de ces derniers comme pesticides
WO2001055144A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'isothiazole et leur utilisation en tant que pesticides
WO2001055139A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derive d'isothiazole et utilisations de ceux-ci sous forme de pesticides
WO2001072726A1 (fr) * 2000-03-27 2001-10-04 Bayer Aktiengesellschaft Derives d'oxime pour lutter contre des micro-organismes et des parasites animaux indesirables
GB2361474A (en) * 2000-03-24 2001-10-24 Syngenta Ltd Novel azole/azine compounds having fungicidal/pesticidal properties
WO2001090105A1 (fr) * 2000-05-25 2001-11-29 Syngenta Limited Isothiazoles utilises en tant que pesticides
WO2002032887A1 (fr) * 2000-10-20 2002-04-25 Syngenta Limited Procede de preparation de 5-amino-3-alkylisothiazoles et de 5-amino-4-chloro-3-alkylisothiazoles
WO2002059120A1 (fr) * 2001-01-26 2002-08-01 Syngenta Limited Processus de preparation de derives d'isothiazole
WO2003011861A1 (fr) * 2001-07-27 2003-02-13 Syngenta Limited Derives d'azole utilises comme insecticides
WO2003051123A1 (fr) * 2001-12-14 2003-06-26 Bayer Cropscience Ag Pesticides a base de derives isothiazolylaminocarbonyle
US6613803B1 (en) 1997-04-22 2003-09-02 Euro-Celtique S.A. Carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones and the use thereof
US6667326B1 (en) 2000-11-16 2003-12-23 Novartis Animal Health Us, Inc. Pesticidal aminoheterocyclamide compounds
USRE38425E1 (en) 1995-06-07 2004-02-10 University Of Saskatchewan Technologies, Inc. Semicarbazones having CNS activity and pharmaceutical preparations containing same
WO2005040143A1 (fr) * 2003-10-27 2005-05-06 Basf Aktiengesellschaft Composes 5-(2-arylacetamido)isothiazole ii
EP1572656A2 (fr) * 2002-12-20 2005-09-14 Dow Agrosciences LLC Composes utilises en tant que pesticides
WO2006017406A1 (fr) * 2004-08-02 2006-02-16 Abbott Laboratories Cyanoamidines antagonistes de p2x7 pour le traitement de la douleur
WO2007007886A1 (fr) * 2005-07-11 2007-01-18 Mitsubishi Tanabe Pharma Corporation Derive d'oxime et ses preparations
WO2008130953A2 (fr) * 2007-04-17 2008-10-30 Abbott Laboratories Nouveaux composés en tant que ligands du récepteur cannabinoïde
US8003675B2 (en) 2006-07-12 2011-08-23 Kumiai Chemical Industry Co., Ltd. 3,4-dihalogenoisothiazole derivative, and agricultural or horticultural plant disease-controlling agent
US8501794B2 (en) 2007-04-17 2013-08-06 Abbvie Inc. Compounds as cannabinoid receptor ligands
US8735434B2 (en) 2007-05-18 2014-05-27 Abbvie Inc. Compounds as cannabinoid receptor ligands
US8841334B2 (en) 2006-05-31 2014-09-23 Abbvie Inc. Compounds as cannabinoid receptor ligands and uses thereof
US8846730B2 (en) 2008-09-08 2014-09-30 Abbvie Inc. Compounds as cannabinoid receptor ligands
US8859596B2 (en) 2008-09-16 2014-10-14 Abbvie Inc. Compounds as cannabinoid receptor ligands
US8865753B2 (en) 2007-03-28 2014-10-21 Abbvie Inc. Compounds as cannabinoid receptor ligands
US8895592B2 (en) 2008-12-16 2014-11-25 Abbvie Inc. Compounds as cannabinoid receptor ligands
US9006275B2 (en) 2006-05-31 2015-04-14 Abbvie Inc. Compounds as cannabinoid receptor ligands and uses thereof
US9193713B2 (en) 2007-10-12 2015-11-24 Abbvie Inc. Compounds as cannabinoid receptor ligands
CN106674215A (zh) * 2016-12-29 2017-05-17 新沂市中诺新材料科技有限公司 一种新型纳米级异噁唑酰胺类农药合成方法

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JP2009062277A (ja) * 2005-12-27 2009-03-26 Nippon Soda Co Ltd ベンゾイソチアゾリン化合物及び有害生物防除剤
JP2009227655A (ja) * 2007-11-16 2009-10-08 Sumitomo Chemical Co Ltd α，β−不飽和イミダート化合物およびそれを含有する有害生物防除剤

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GB1548397A (en) * 1976-06-01 1979-07-11 Lilly Industries Ltd Acylated amino-isoxazoles and aminoisothiazoles

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DE1924830A1 (de) * 1968-07-06 1970-11-19 Merck Patent Gmbh Neues Verfahren zur Herstellung von 5-Acylamino-isothiazolderivaten
US4013675A (en) * 1975-05-05 1977-03-22 Ppg Industries, Inc. N-(3-methyl-5-isothiazolyl)-2-methylpentanamide
GB1548397A (en) * 1976-06-01 1979-07-11 Lilly Industries Ltd Acylated amino-isoxazoles and aminoisothiazoles
US4059433A (en) * 1976-06-18 1977-11-22 Fmc Corporation 3-Alkoxyisothiazole derivatives as herbicides

Cited By (65)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE38425E1 (en) 1995-06-07 2004-02-10 University Of Saskatchewan Technologies, Inc. Semicarbazones having CNS activity and pharmaceutical preparations containing same
US5972843A (en) * 1995-11-14 1999-10-26 Bayer Aktiengesellschaft Acylated 5-aminoisothiazoles with insecticidal properties, intermediate products and process for producing them
CN1071749C (zh) * 1995-11-14 2001-09-26 拜尔公司 具有杀虫性能的酰化5－氨基异噻唑、中间产物及其制法
US6008366A (en) * 1995-11-14 1999-12-28 Bayer Aktiengesellschaft Acylated 5-aminoisothiazoles with insecticidal properties, intermediate products and process for producing them
WO1997018198A1 (fr) * 1995-11-14 1997-05-22 Bayer Aktiengesellschaft 5-aminoisothiazoles acyles avec effet insecticide, produits intermediaires et procede de production correspondant
WO1998002424A1 (fr) * 1996-07-16 1998-01-22 Bayer Aktiengesellschaft N-(5-isothiazolyl)-thioamides substitues
WO1998005670A1 (fr) * 1996-07-31 1998-02-12 Bayer Aktiengesellschaft N-isothiazolyl-(thio)amides substitues
US6613803B1 (en) 1997-04-22 2003-09-02 Euro-Celtique S.A. Carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones and the use thereof
US6638947B2 (en) 1997-04-22 2003-10-28 Euro-Celtique S.A. Carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones and the use thereof
US6696442B2 (en) 1997-04-22 2004-02-24 Euro-Celtique S.A. Carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones and the use thereof
WO1999000375A1 (fr) * 1997-06-26 1999-01-07 Bayer Aktiengesellschaft Aminoheterocyclylamides substitues
WO1999010334A1 (fr) * 1997-08-22 1999-03-04 Bayer Aktiengesellschaft 5-aminoisothiazoles acyles a usage de pesticides et de fungicides
WO2000006566A1 (fr) * 1998-07-30 2000-02-10 Syngenta Limited Derives de benzoxazole, benzthiazole et benzimidazole
US6544989B2 (en) 1998-07-30 2003-04-08 Syngenta Limited Benzazoles: benzoxazole, benzthiazole and benzimidazole derivatives
AU755291B2 (en) * 1998-07-30 2002-12-12 Syngenta Limited Benzazoles: benzoxazole, benzthiazole and benzimidazole derivatives
US6403622B1 (en) 1998-10-06 2002-06-11 Bayer Aktiengesellschaft Phenylacetic acid heterocyclyl amides having an insecticidal effect
WO2000020415A1 (fr) * 1998-10-06 2000-04-13 Bayer Aktiengesellschaft Heterocyclylamides d'acide phenylacetique ayant un effet insecticide
WO2000063207A1 (fr) * 1999-04-20 2000-10-26 Syngenta Limited Derives indazole ou benzotriazole pesticides
US7112553B1 (en) * 1999-04-20 2006-09-26 Syngenta Limited Pesticidal indazole or benzotriazole derivatives
AU772298B2 (en) * 1999-04-20 2004-04-22 Syngenta Limited Pesticidal indazole or benzotriazole derivatives
WO2000068214A1 (fr) * 1999-05-10 2000-11-16 Syngenta Limited Procede de preparation de composes 5-amino-3-alkylisothiazole et de composes 5-amino-4-chloro-3-alkylisothiazole
WO2001036415A1 (fr) * 1999-11-18 2001-05-25 Novartis Ag Composes pesticides aminoheterocyclamide
WO2001055140A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'isothiazole et utilisation de ces derniers comme pesticides
WO2001055139A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derive d'isothiazole et utilisations de ceux-ci sous forme de pesticides
US6703347B2 (en) 2000-01-28 2004-03-09 Syngenta Limited Isothiazole derivatives and their use as pesticides
WO2001055141A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine comme pesticides
EP1686128A3 (fr) * 2000-01-28 2007-01-24 Syngenta Limited Dérivés de l'isothiazole et leur utilisation comme pesticides
WO2001055142A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'isothiazole et leur utilisation comme pesticides
WO2001055137A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine et leur utilisation comme pesticides
WO2001055145A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine en tant que pesticides
EP1686128A2 (fr) 2000-01-28 2006-08-02 Syngenta Limited Dérivés de l'isothiazole et leur utilisation comme pesticides
WO2001055135A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'azine utilises comme pesticides
WO2001055144A1 (fr) * 2000-01-28 2001-08-02 Syngenta Limited Derives d'isothiazole et leur utilisation en tant que pesticides
GB2361474A (en) * 2000-03-24 2001-10-24 Syngenta Ltd Novel azole/azine compounds having fungicidal/pesticidal properties
WO2001072726A1 (fr) * 2000-03-27 2001-10-04 Bayer Aktiengesellschaft Derives d'oxime pour lutter contre des micro-organismes et des parasites animaux indesirables
WO2001090105A1 (fr) * 2000-05-25 2001-11-29 Syngenta Limited Isothiazoles utilises en tant que pesticides
WO2002032887A1 (fr) * 2000-10-20 2002-04-25 Syngenta Limited Procede de preparation de 5-amino-3-alkylisothiazoles et de 5-amino-4-chloro-3-alkylisothiazoles
US6667326B1 (en) 2000-11-16 2003-12-23 Novartis Animal Health Us, Inc. Pesticidal aminoheterocyclamide compounds
WO2002059120A1 (fr) * 2001-01-26 2002-08-01 Syngenta Limited Processus de preparation de derives d'isothiazole
WO2003011861A1 (fr) * 2001-07-27 2003-02-13 Syngenta Limited Derives d'azole utilises comme insecticides
WO2003051123A1 (fr) * 2001-12-14 2003-06-26 Bayer Cropscience Ag Pesticides a base de derives isothiazolylaminocarbonyle
EP1572656A2 (fr) * 2002-12-20 2005-09-14 Dow Agrosciences LLC Composes utilises en tant que pesticides
EP1572656A4 (fr) * 2002-12-20 2006-09-06 Dow Agrosciences Llc Composes utilises en tant que pesticides
WO2005040143A1 (fr) * 2003-10-27 2005-05-06 Basf Aktiengesellschaft Composes 5-(2-arylacetamido)isothiazole ii
US7241776B2 (en) 2004-08-02 2007-07-10 Abbott Laboratories Cyanoamidine P2X7 antagonists for the treatment of pain
WO2006017406A1 (fr) * 2004-08-02 2006-02-16 Abbott Laboratories Cyanoamidines antagonistes de p2x7 pour le traitement de la douleur
AU2006267387B2 (en) * 2005-07-11 2010-11-18 Mitsubishi Tanabe Pharma Corporation An oxime derivative and preparations thereof
US7514439B2 (en) 2005-07-11 2009-04-07 Mitsubishi Tanabe Pharma Corporation Oxime derivative and preparations thereof
WO2007007886A1 (fr) * 2005-07-11 2007-01-18 Mitsubishi Tanabe Pharma Corporation Derive d'oxime et ses preparations
US8119626B2 (en) 2005-07-11 2012-02-21 Mitsubishi Tanabe Pharma Corporation Oxime derivative and preparations thereof
US8841334B2 (en) 2006-05-31 2014-09-23 Abbvie Inc. Compounds as cannabinoid receptor ligands and uses thereof
US9006275B2 (en) 2006-05-31 2015-04-14 Abbvie Inc. Compounds as cannabinoid receptor ligands and uses thereof
US8003675B2 (en) 2006-07-12 2011-08-23 Kumiai Chemical Industry Co., Ltd. 3,4-dihalogenoisothiazole derivative, and agricultural or horticultural plant disease-controlling agent
US8865753B2 (en) 2007-03-28 2014-10-21 Abbvie Inc. Compounds as cannabinoid receptor ligands
WO2008130953A3 (fr) * 2007-04-17 2008-12-11 Abbott Lab Nouveaux composés en tant que ligands du récepteur cannabinoïde
US7872033B2 (en) 2007-04-17 2011-01-18 Abbott Laboratories Compounds as cannabinoid receptor ligands
US8501794B2 (en) 2007-04-17 2013-08-06 Abbvie Inc. Compounds as cannabinoid receptor ligands
WO2008130953A2 (fr) * 2007-04-17 2008-10-30 Abbott Laboratories Nouveaux composés en tant que ligands du récepteur cannabinoïde
US8835475B2 (en) 2007-04-17 2014-09-16 Abbvie Inc. Compounds as cannabinoid receptor ligands
US8735434B2 (en) 2007-05-18 2014-05-27 Abbvie Inc. Compounds as cannabinoid receptor ligands
US9193713B2 (en) 2007-10-12 2015-11-24 Abbvie Inc. Compounds as cannabinoid receptor ligands
US8846730B2 (en) 2008-09-08 2014-09-30 Abbvie Inc. Compounds as cannabinoid receptor ligands
US8859596B2 (en) 2008-09-16 2014-10-14 Abbvie Inc. Compounds as cannabinoid receptor ligands
US8895592B2 (en) 2008-12-16 2014-11-25 Abbvie Inc. Compounds as cannabinoid receptor ligands
CN106674215A (zh) * 2016-12-29 2017-05-17 新沂市中诺新材料科技有限公司 一种新型纳米级异噁唑酰胺类农药合成方法

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CA2189573A1 (fr) 1995-11-23
AU2641295A (en) 1995-12-05

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