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WO2000003975A2 - Derives d'arylvinylether et leur utilisation comme herbicides - Google Patents

Derives d'arylvinylether et leur utilisation comme herbicides Download PDF

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Publication number
WO2000003975A2
WO2000003975A2 PCT/EP1999/005470 EP9905470W WO0003975A2 WO 2000003975 A2 WO2000003975 A2 WO 2000003975A2 EP 9905470 W EP9905470 W EP 9905470W WO 0003975 A2 WO0003975 A2 WO 0003975A2
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Prior art keywords
methyl
methoxypropenoate
compound
optionally substituted
alkyl
Prior art date
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PCT/EP1999/005470
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English (en)
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WO2000003975A3 (fr
Inventor
Nicholas Charles Ray
Catherine Jacqueline White
Michael Gingell
Simon Neil Pettit
Gilles Raphy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Agriculture Ltd
Original Assignee
Aventis Agriculture Ltd
Rhone Poulenc Agriculture Ltd
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Priority claimed from GBGB9815508.8A external-priority patent/GB9815508D0/en
Application filed by Aventis Agriculture Ltd, Rhone Poulenc Agriculture Ltd filed Critical Aventis Agriculture Ltd
Priority to JP2000560084A priority Critical patent/JP2002520384A/ja
Priority to AU54158/99A priority patent/AU5415899A/en
Priority to EP99940084A priority patent/EP1097117A2/fr
Publication of WO2000003975A2 publication Critical patent/WO2000003975A2/fr
Publication of WO2000003975A3 publication Critical patent/WO2000003975A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/803—Processes of preparation
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/64—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
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    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
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    • C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/20—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having nitrogen atoms of amidino groups acylated
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C311/04—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
    • C07C311/49—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/54—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/02—Thiocyanates
    • C07C331/10—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/02—Thiocyanates
    • C07C331/14—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
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    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C07D295/30—Nitrogen atoms non-acylated
    • C—CHEMISTRY; METALLURGY
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D333/40—Thiophene-2-carboxylic acid

Definitions

  • the invention relates to novel aryl vinyl ethers having herbicidal properties, compositions containing them, processes and intermediates for their preparation, a method of controlling weeds by means of such compositions and the safening of aryl vinyl ethers with antidotal or safener compounds.
  • An object of this invention is to provide new aryl vinyl ether derivatives useful as highly effective herbicides, and processes for their preparation.
  • Another object of the instant invention is to provide herbicides which are effective against grasses in addition to broad-leafed weeds. Another object is to provide herbicides which possess selective herbicidal activity.
  • Another object is to provide herbicides which possess good residual activity.
  • Aryl vinyl ether compounds under certain conditions can produce damage in crop plants, particularly cereal crop plants such as maize and -?-
  • the present invention provides compounds of formula (I):
  • X 2 is O, S, NR 18 or a simple bond (preferably O, S or NR 18 ); X 3 is N or CR 19 ;
  • R 17 and R 18 independently represent a hydrogen atom or an optionally substituted group R , R , R or R , wherein; R 20 represents a lower alkyl radical; R 21 represents a lower alkenyl radical; R 22 represents a lower alkynyl radical; R 23 represents a -(CH 2 )m-phenyl radical; m represents zero or one; R 16 is R 24 or OR 25 or SR 25 , NR 25 R 26 or alkyl substituted by alkoxycarbonyl;
  • R 10 represents a radical selected from
  • R 27 , R 28 and R 281 represent the same or different halogen atoms;
  • R 29 and R 291 represent OR 37 or SR 37 or,
  • R 37 represents lower alkyl, lower haloalkyl, lower alkenyl or lower haloalkenyl ;
  • R 1 'and R 13 each independently represent hydrogen or alkyl, or
  • R u and R 13 may be a single divalent radical comprising one to six atoms on the main chain, this main chain optionally containing one to three nitrogen atoms, one oxygen atom or one sulphur atom; this divalent radical forming with the two carbon atoms to which they are attached, a saturated or non-saturated carbocyclic or heterocyclic ring (for example phenyl or pyridyl) or a bicyclic ring, these rings being optionally substituted by from one to four R radicals, each ring containing at most eight ring members, preferably at most six, wherein R 15 represents a halogen atom, hydroxy, cyano, lower alkoxycarbonyl, lower alkyl, lower alkenyl, lower alkynyl, optionally substituted cycloalkyl, lower alkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower haloalkoxycarbonyl, lower
  • R b and R c together with the C atoms to which they are attached form a 5 or 6 -membered cyclic acetal group
  • R 1 , 0 ⁇ Rr represents a group (A), (B), (C), (D) or (E):
  • R d , R c , R f , R g and R h represent H, lower alkyl, halogen or OH, and n represents the values 0, 1, 2 or 3;
  • the aryl vinyl ether derivatives of the present invention have two possible stereoisomers, (Z) and (E) isomers, as defined in the Cahn- Ingold-Prelog rules at a double bond. It will be understood that the present invention embraces both the pure isomers and mixtures which may be more or less enriched mixtures thereof. Furthermore it is understood that the compounds of formula (I) wherein R 10 , R 11 , R 12 , R 13 , R 14 and R 17 are as defined above, X 3 is CR 19 and in which R 16 is OR 25 wherein R is hydrogen, may exist in a tautomeric form and acetal forms thereof.
  • Suitable salts with bases include alkali metal (e.g. sodium and potassium), alkaline earth metal (e.g. calcium and magnesium), ammonium and amine (e.g. diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine) salts.
  • alkali metal e.g. sodium and potassium
  • alkaline earth metal e.g. calcium and magnesium
  • ammonium and amine e.g. diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine
  • compounds of formula I containing an amino group include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids for example acetic acid.
  • Formyl groups may exist as their hydrates i.e. as the dihydroxymethyl form.
  • all of the optionally substituted groups may have as the optional substituent one or more halogen atoms, among other possible substituents.
  • cycloalkyl radicals the following may be selected; lower alkyl, lower alkenyl, lower alkynyl, lower haloalkyl and halogen.
  • halogen atom means fluorine, chlorine, bromine or iodine
  • alkyl, alkenyl and alkynyl radicals may be straight- or branched- chain groups
  • cycloalkyl groups have from three to six carbon atoms in the ring
  • lower for a radical means that the said radical may have up to 8 carbon atoms (preferably up to 6), which are straight or branched chain.
  • preferred groups of the compounds include those compounds of general formula (I) in which;
  • R ⁇ and R 13 form a non-saturated carbocyclic ring (preferably phenyl) substituted by a halogen atom (preferably chlorine or fluorine); or R 11 and R 13 represent a pyridine ring; or R 1 1 and R 13 represent a phenyl ring which is fused at the o- and m- positions (relative to the R group) to a saturated or unsaturated 5 or 6-membered carbocyclic ring; X 3 is CR 19 wherein R 19 represents a hydrogen atom; X 2 is an oxygen atom;
  • Xi is an oxygen or sulphur atom (preferably an oxygen atom);
  • R 16 is a hydrogen atom or lower alkyl group (preferably methyl) or OR 25 wherein R 25 represents a lower alkyl group or a hydrogen atom
  • R 17 is a hydrogen atom or lower alkyl group (preferably methyl).
  • a preferred class of compounds of formula (I) are those in which: R n and R 13 form a phenyl or naphthyl ring substituted by one or more halogen, alkyl or haloalkyl groups; X 3 is CR 19 wherein R 19 represents a hydrogen atom; Xi and X each represent an oxygen atom; R 16 and R I7 each represent a methyl group; and R 10 is -CO 2 R 32 .
  • R 11 and R 13 form a phenyl or naphthyl ring substituted by one or more halogen, alkyl or haloalkyl groups;
  • X is CR 19 wherein R 19 represents a hydrogen atom; Xi and X 2 each represent an oxygen atom; R and R each represent a methyl group; and R is -CO 2 R in which R 32 is lower alkyl or hydrogen.
  • R 10 represents CO 2 R 32 , wherein R 32 is as hereinbefore defined and in which R 15 , R 25 and R 17 have the meanings indicated hereinbelow.
  • Identification Group I recites individual species in which R 32 represents, hydrogen, Na, Me, Et, n-Pr, i-Pr, c-Pr-methyl, n- Bu, 2-Bu, Pen, c-Pen, c-Hex, Bn, 2-heptyl, octyl, 2-octyl, 2,2,2- trifluoroethyl, 3-chloroprop-l-yl, propargyl, methoxyethyl, ethoxyethyl, allyl.
  • the R 15 group is located according to the numbering system in (I- 2) and (1-7) and when more than one R 15 substituent is present, the various meanings have been placed in the same column.
  • R 10 , R , 15 and X have the meanings indicated hereinbelow.
  • the R 1 group is located according to the numbering system in (1-14).
  • compounds of formula (I) wherein the various symbols are as defined above and in which R 10 represents -CO 2 H may be prepared from the corresponding compound wherein R represents -CO 2 R 3 and R 33 represents t-butyl, using an acid such as trifluoroacetic acid in a solvent such as dichloromethane at a temperature of from 0-50°C.
  • compounds of formula (I) wherein the various symbols are as defined above and in which R 10 represents -CONR 30 R 31 may be prepared from the corresponding compound of formula (I) wherein R 10 represents -CO 2 H by successive treatment with a halogenating agent to give the acyl halide, followed by an amine of formula (III):
  • the halogenating agent is generally an oxalyl halide or a sulfonyl halide, the halide; is preferably chloride.
  • the halogenation can be performed in the presence or absence of solvent, preferably in an halogenated hydrocarbon such as dichloromethane at a temperature between 0 °C and 40 °C, optionally in the presence of a dialkylformamide as catalyst, usually dimethylformamide.
  • the reaction of the thus formed acyl halide with an amine of formula (III) is generally performed in an inert solvent such as dichloromethane, optionally in the presence of a base, generally a tertiary amine base such as triethylamine, at a temperature between 0 °C and 40 °C.
  • an inert solvent such as dichloromethane
  • a base generally a tertiary amine base such as triethylamine
  • compounds of formula (I) wherein the various symbols are as defined above, in which R 10 is -CH 2 NO 2 , -CH 2 SCN, -CH 2 CN or -CH 2 N 3 may be prepared from the corresponding compound of formula (I) wherein R 10 is -CH ⁇ -L, where L is a leaving group, generally a sulfonate ester such as a para toluenesulfonate or a mesylate, or wherein R 10 is replaced by -CH 2 -L', where L 1 is a leaving group, generally a halogen, by treatment with the metal salt of the appropriate nitro, thiocyano, cyano or azido anion respectively, especially a group la or lb metal salt, such as sodium, potassium or silver, in an organic solvent such as dimethylformamide or dimethylsulfoxide, at a temperature between 0 °C and 150 °C, preferably 0° to 60 °C
  • reaction optionally in the presence of an organic solvent, such as toluene, acetic acid or an alcohol such as methanol or ethanol, optionally in the presence of an acid, such as para-toluene sulfonic acid or a base, such as sodium acetate, as catalyst.
  • organic solvent such as toluene, acetic acid or an alcohol such as methanol or ethanol
  • an acid such as para-toluene sulfonic acid or a base, such as sodium acetate
  • a base such as sodium acetate
  • the halogen is preferably bromine or iodine.
  • the reaction can be conducted in the absence or presence of solvent, which may be organic or aqueous, generally a polar aprotic solvent such as ⁇ , ⁇ - dimethylformamide or a polyether such as glyme.
  • solvent which may be organic or aqueous, generally a polar aprotic solvent such as ⁇ , ⁇ - dimethylformamide or a polyether such as glyme.
  • the reaction is usually carried out in the presence of a transition metal compound as catalyst, usually of palladium, such as palladium acetate, optionally in the presence of a base, for example triethylamine and other catalysts such as trialkyl or triaryl phosphines, generally triphenylphosphine.
  • the reactions are performed at temperatures from 0°C to 150 °C, generally
  • an alkylating agent to introduce a group R 251 which is alkyl
  • a dialkysulfate such as dimethylsulfate
  • an alkyl halide preferably an alkyl iodide such as methyl iodide.
  • the reaction may be performed in the absence or presence of an organic solvent, such as an ether such as diethyl ether, or a dialkylformamide, such as dimethylformamide, at a temperature between 0° and 40 °C, optionally in the presence of a base which may be organic, such as a tertiary amine, or inorganic, such as a metal carbonate or a metal bicarbonate, such as potassium carbonate.
  • methyl 2-(2-t-butyloxycarbonyl-4-chlorophenoxy)-3- hydroxypropenoate was mixed with 336mg of K 2 CO 3 , (CH 3 ) 2 SO (0.16ml) and dimethylformamide (8.2ml). The mixture was stirred for 12 hours at 20°C and extracted with ether (following the addition of Na 2 CO 3 ). The organic layer was washed with water and brine and dried so as to give, methyl 2-(2-t-butyloxycarbonyl-4-chlorophenoxy)-3- methoxypropenoate (compound 1), M.S. analysis showed m/z 343 (M+H).
  • Example 5 lOOmg of methyl 2-(2-bromomethyl-4-chlorophenoxy)-3- methoxyacrylate were mixed with 70mg of N-methylmorpholine N- oxide monohydrate and stirred in acetonitrile at 20°C for 12 hours in the presence of sieves as a drying agent. The mixture was filtered, washed with water and dried so as to give 56mg of methyl 2-(2-formyl-4- chlorophenoxy)-3-methoxypropenoate (compound 5), M.S. m/z 271 (M+H).
  • Example 13 42 mg of methyl 2-(2-carboxy-4-chlorophenoxy)-3- methoxypropenoate dissolved in a mixture of diethyl ether (0.8 ml) and tetrahydrofuran (0.4 ml) were added to 7.5 mg of a 60% dispersion of sodium hydride in mineral oil. The mixture was stirred at ambient temperature for 4 hours to give a white precipitate that was filtered, washed with ether and dried to give methyl 2-(2-carboxy-4- chlorophenoxy)-3-methoxypropenoate, sodium salt (compound 43), mp 230-234 °C (decomposed).
  • methyl 2-(2-carboxy-4-iodophenoxy)-3-methoxypropenoate sodium salt (compound 116, mp 234-235°C) was prepared.
  • Example 14 50 mg of methyl 2-(2-bromo-4-chlorophenoxy)-3- methoxypropenoate, 30 ⁇ l of triethylamine, 3.4 mg of triphenylphosphine, 40 ⁇ l of methyl acrylate, 1.4 mg of palladium acetate and DMF (2 ml) were stirred at 100 °C for 24 hours. The reaction mixture was worked up with 2N HCI, extracted into ethyl acetate, dried and concentrated. Column chromatography gave methyl 2-(4-chloro-2-
  • Methyl magnesium iodide (0.112ml of a 3M solution) was added dropwise to a stirred solution of methyl 2-(4-chloro-2-formylphenoxy)- 3-methoxypropenoate (0. lg) in toluene. After 1 hour the solvent was evaporated and the residue partitioned between hydrochloric acid (2M) and ethyl acetate.
  • Oxalyl chloride (0.4ml) and N,N-dimethylformamide were added to a solution of methyl 2-(2-carboxy-4-chlorophenoxy)-3- methoxypropenoate (l.Og) in dichloromethane and stirred at reflux for 2 hours and evaporated.
  • a solution of the residue in tetrahydrofuran was added dropwise to a solution of trimethylsilyldiazomethane (2.2ml of a 2M solution in hexane) and triethylamine (0.6ml) in tetrahydrofuran at 0°C. The mixture was kept at 0°C overnight, evaporated and partitioned between sodium bicarbonate solution and ethyl acetate.
  • Cyanuric fluoride (39.6mg) and pyridine (1 1.6mg) were added to a solution of methyl 2-(2-carboxy-4-chlorophenoxy)-3- methoxypropenoate (42mg) in dichloromethane, and stirred at 20°C under nitrogen for 4 hours.
  • Oxalyl chloride (0.4ml) was added to a solution of methyl 2-(2- carboxy-4-chlorophenoxy)-3-methoxypropenoate (l.Og) in dichloromethane containing N,N-dimethylformamide (1 drop) and stirred at reflux for 2 hours. After evaporation, the residue was dissolved in toluene, and a solution of t-butyl-3-cyclopropyl-3- oxopropanoate magnesium methoxide enolate (1.05g) in toluene added, and the mixture stirred overnight. Hydrochloric acid (2M) was added and stirrred for 5 minutes. The organic phase was washed (water), dried
  • a method for controlling the growth of weeds i.e. undesired vegetation
  • a herbicidally effective amount of at least one aryl vinyl ether derivative of formula (I) or an agriculturally acceptable salt or metal complex thereof comprises applying to the locus a herbicidally effective amount of at least one aryl vinyl ether derivative of formula (I) or an agriculturally acceptable salt or metal complex thereof.
  • the aryl vinyl ether derivatives are normally used in the form of herbicidal compositions (i.e. in association with compatible diluents or carriers and/or surface active agents suitable for use in herbicidal compositions), for example as hereinafter described.
  • the amounts of compounds of formula (I) applied vary with the nature of the weeds, the compositions used, the time of application, the climatic and edaphic conditions and (when used to control the growth of weeds in crop-growing areas) the nature of the crops.
  • the rate of application should be sufficient to control the growth of weeds without causing substantial permanent damage to the crop.
  • application rates between lg and lOOOg of active material per hectare give good results. However, it is to be understood that higher or lower application rates may be used, depending upon the particular problem of weed control encountered.
  • the compounds of formula (I) may be used to control selectively the growth of weeds, for example to control the growth of those species hereinbefore mentioned, by pre- or post-emergence application in a directional or non-directional fashion, e.g. by directional or non- directional spraying, to a locus of weed infestation which is an area used, or to be used, for growing crops, for example cereals, e.g. wheat, barley, oats, maize and rice, soybean, field and dwarf beans, peas, lucerne, cotton, peanuts, flax, onions, carrots, cabbage, oilseed rape, sunflower, sugar beet, and permanent or sown grassland before or after sowing of the crop or before or after emergence of the crop.
  • cereals e.g. wheat, barley, oats, maize and rice, soybean, field and dwarf beans, peas, lucerne, cotton, peanuts, flax, onions, carrots, cabbage, oilseed rape, sunflower, sugar bee
  • the compounds of formula (I) may also be used to control the growth of weeds, especially those indicated above, by pre- or post- emergence application in established orchards and other tree-growing areas, for example forests, woods and parks, and plantations, e.g. sugar cane, oil palm and rubber plantations.
  • plantations e.g. sugar cane, oil palm and rubber plantations.
  • they may be applied in a directional or non- directional fashion (e.g. by directional or non-directional spraying) to the weeds or to the soil in which they are expected to appear, before or after planting of the trees or plantations at application rates between 50g and 5000g, and preferably between 50g and 2000g, most preferably between lOOg and lOOOg of active material per hectare.
  • the compounds of formula (I) may also be used to control the growth of weeds, especially those indicated above, at loci which are not crop-growing areas but in which the control of weeds is nevertheless desirable.
  • non-crop-growing areas examples include airfields, industrial sites, railways, roadside verges, the verges of rivers, irrigation and other waterways, scrublands and fallow or uncultivated land, in particular where it is desired to control the growth of weeds in order to reduce fire risks.
  • the active compounds When used for such pu ⁇ oses in which a total herbicidal effect is frequently desired, the active compounds are normally applied at dosage rates higher than those used in crop-growing areas as hereinbefore described. The precise dosage will depend upon the nature of the vegetation treated and the effect sought.
  • the compounds of formula (I) may be inco ⁇ orated into the soil in which the weeds are expected to emerge. It will be appreciated that when the compounds of formula (I) are used to control the growth of weeds by post-emergence application, i.e. by application to the aerial or exposed portions of emerged weeds, the compounds of formula (I) will also normally come into contact with the soil and may also then exercise a pre-emergence control on later-germinating weeds in the soil.
  • compositions suitable for herbicidal use comprising one or more of the aryl vinyl ethers of formula (I) or an agriculturally acceptable salt or metal complex thereof, in association with, and preferably homogeneously dispersed in, one or more compatible agriculturally- acceptable diluents or carriers and/or surface active agents [i.e. diluents or carriers and/or surface active agents of the type generally accepted in the art as being suitable for use in herbicidal compositions and which are compatible with compounds of formula (I)].
  • the term "homogeneously dispersed” is used to include compositions in which the compounds of formula ⁇ !) are dissolved in other components.
  • herbicidal compositions is used in a broad sense to include not only compositions which are ready for use as herbicides but also concentrates which must be diluted before use.
  • the compositions contain from 0.05 to 90% by weight of one or more compounds of formula (I).
  • the herbicidal compositions may contain both a diluent or carrier and surface-active (e.g. wetting, dispersing, or emulsifying) agent.
  • the herbicidal compositions according to the present invention may comprise up to 10% by weight, e.g.
  • herbicidal compositions according to the present invention may comprise higher proportions of surface-active agent, for example up to 15% by weight in liquid emulsifiable suspension concentrates and up to 25% by weight in liquid water soluble concentrates.
  • suitable solid diluents or carriers are aluminium silicate, microfine silicon dioxide, talc, chalk, calcined magnesia, kieselguhr, tricalcium phosphate, powdered cork, adsorbent carbon black and clays such as kaolin and bentonite.
  • suitable solid diluents or carriers are aluminium silicate, microfine silicon dioxide, talc, chalk, calcined magnesia, kieselguhr, tricalcium phosphate, powdered cork, adsorbent carbon black and clays such as kaolin and bentonite.
  • Granular formulations may be prepared by absorbing the compounds of formula (I) (dissolved in suitable solvents, which may, if desired, be volatile) onto the solid diluents or carriers in granular form and, if desired, evaporating the solvents, or by granulating compositions in powder form obtained as described above.
  • Solid herbicidal compositions, particularly wettable powders and granules may contain wetting or dispersing agents (for example of the types described above), which may also, when solid, serve as diluents or carriers.
  • Liquid compositions according to the invention may take the form of aqueous, organic or aqueous-organic solutions, suspensions and emulsions which may inco ⁇ orate a surface-active agent.
  • Suitable liquid diluents for inco ⁇ oration in the liquid compositions include water, glycols, glycol ethers, tetrahydrofurfuryl alcohol, acetophenone, cyclohexanone, isophorone, N-alkyl pyrrolidones, toluene, xylene, mineral, animal and vegetable oils, esterified vegetable oils and light aromatic and naphthenic fractions of petroleum (and mixtures of these diluents).
  • Surface-active agents, which may be present in the liquid compositions may be ionic or non-ionic (for example of the types described above) and may, when liquid, also serve as diluents or carriers.
  • Powders, dispersible granules and liquid compositions in the form of concentrates may be diluted with water or other suitable diluents, for example mineral or vegetable oils, particularly in the case of liquid concentrates in which the diluent or carrier is an oil, to give compositions ready for use.
  • suitable diluents for example mineral or vegetable oils, particularly in the case of liquid concentrates in which the diluent or carrier is an oil, to give compositions ready for use.
  • liquid compositions of the compound of formula (I) may be used in the form of self-emulsifying concentrates containing the active substances dissolved in the emulsifying agents or in solvents containing emulsifying agents compatible with the active substances, the simple addition of such concentrates to water producing compositions ready for use.
  • Liquid concentrates in which the diluent or carrier is an oil may be used without further dilution using the electrostatic spray technique.
  • Herbicidal compositions according to the present invention may also contain, if desired, conventional adjuvants such as adhesives, protective colloids, thickeners, penetrating agents, spreading agents, stabilisers, sequestering agents, anti-caking agents, colouring agents and corrosion inhibitors. These adjuvants may also serve as carriers or diluents.
  • liquid emulsifiable suspension concentrates which comprise from 10 to 70% of one or more compounds of formula (I), from 5 to 15% of surface-active agent, from 0.1 to 5% of thickener and from 10 to 84.9% of organic solvent, e.g. mineral oil; water dispersible granules which comprise from 1 to 90%, e.g. 25 to 75% of one or more compounds of formula (I), from 1 to 15%, e.g.
  • emulsifiable concentrates which comprise 0.05 to 90%, and preferably from 1 to 60% of one or more compounds of formula (I), from 0.01 to 10%, and preferably from 1 to 10%, of surface-active agent and from 9.99 to 99.94%, and preferably from 39 to 98.99%, of organic solvent.
  • Herbicidal compositions according to the present invention may also comprise the compounds of formula ⁇ !) in association with, and preferably homogeneously dispersed in, one or more other pesticidally active compounds and, if desired, one or more compatible pesticidally acceptable diluents or carriers, surface-active agents and conventional adjuvants as hereinbefore described.
  • herbicides for example to increase the range of weed species controlled for example alachlor [2-chloro-2,6'- diethyl-N-(methoxy-methyl)-acetanilide], amidosulfuron, which is 1- (4,6-dimethoxypyrimidin-2-yl)-3-mesyl(methyl)sulfamoylurea, atrazine [2-chloro-4-ethylamino-6-isopropylamino- 1 ,3,5-triazine], bromoxynil [3,5-dibromo-4-hydroxybenzonitrile], chlortoluron [N'-(3-chloro-4- methylphenyl)-N,N-dimethylurea], cinidon-ethyl, which is ethyl (Z)-2- chloro-3-[2-chloro-5-( 1 )
  • synthetic pyrethroids e.g. permethrin and cypermethrin
  • fungicides e.g. carbamates, e.g. methyl N-(l-butyl- carbamoyl- benzimidazol-2-yl)carbamate, and triazoles e.g. l-(4-chloro- phenoxy)-3 ,3- dimethyl- 1 -( 1 ,2,4-triazol- 1 -y I)-butan-2-one.
  • Pesticidally active compounds and other biologically active materials which may be included in, or used in conjunction with, the herbicidal compositions of the present invention, for example those hereinbefore mentioned, and which are acids or bases, may, if desired, be utilized in the form of conventional derivatives, for example alkali metal and amine salts and esters.
  • the following Examples illustrate herbicidal compositions according to the present invention. The following trade marks appear in the Examples: Synperonic, Solvesso, Arylan, Arkopon, Sopropon, Tixosil, Soprophor, Attagel, Rhodorsil.
  • the Active Ingredient listed in the following examples refers to compounds of general formula (I).
  • Example Cl An emulsifiable concentrate is formed from:
  • NMP N-Methylpyrrolidinone
  • CaDDBS Calcium dodecylbenzenesulphonate
  • NPEOPO Nonylphenol ethylene oxide propylene oxide condensate
  • Aromatic solvent Solvesso
  • a wettable powder is formed from:
  • a suspension concentrate is formed from: Active Ingredient 50% w/v
  • a water dispersible granule is formed from: Active Ingredient 50% w/w
  • Microfine silicon dioxide (Tixosil 38) 3% w/w by blending the above ingredients together, grinding the mixture in an air jet mill and granulating by addition of water in a suitable granulation plant (e.g. Fluid bed drier) and drying.
  • a suitable granulation plant e.g. Fluid bed drier
  • the active ingredient may be ground either on its own or admixed with some or all of the other ingredients.
  • Seed of various broad-leaf and grass weed species were sown and herbicide, dissolved in a mixture of acetone and water, was applied at a rate of 62g/ha to the soil surface.
  • the said weeds are Amaranthus retroflexus. Abutilon theophrasti. Galium aparine. Setaria viridis. Alopecurus myosuroides. A vena fatua and Echinochloa crus-galli.
  • Herbicide, furilazole, benoxacor, dichlormid, cloquintocet, fenchlorazole, naphthalic anhydride and R29148 were applied as technical materials prepared in acetone. Mixtures of the Herbicide and safeners were applied post-emergence. Two weeks after treatment the percent reduction in plant growth, compared to an untreated control (the Herbicide sprayed alone), was assessed.
  • the safeners provided an antidotal effect on maize and wheat by decreasing the extent of injury caused by the Herbicide.
  • EXPERIMENTAL EXAMPLE 4 Representative compounds of formula (I), Compounds 2 and 82 and cloquintocet-mexyl, were applied as technical materials prepared in acetone to a locus comprising a natural population of Galium aparine and wheat (Triticum aestivum).
  • the percent reduction in plant growth, compared to an untreated control was assessed 20 and 33 days after treatment (DAT).

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  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
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Abstract

L'invention concerne des dérivés d'arylvinyléther représentés par la formule générale (I). Pour les besoins de ladite formule, les substituants sont tels que définis dans l'invention. L'invention concerne en outre des compositions renfermant les dérivés considérés, ainsi que des procédés et des intermédiaires utilisés pour leur élaboration. L'invention concerne enfin un procédé permettant d'éliminer les mauvaises herbes en utilisant ce type de composition.
PCT/EP1999/005470 1998-07-16 1999-07-16 Derives d'arylvinylether et leur utilisation comme herbicides Ceased WO2000003975A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2000560084A JP2002520384A (ja) 1998-07-16 1999-07-16 アリールビニルエーテル誘導体およびそれらの除草剤としての使用
AU54158/99A AU5415899A (en) 1998-07-16 1999-07-16 Aryl vinyl ether derivatives and their use as herbicides
EP99940084A EP1097117A2 (fr) 1998-07-16 1999-07-16 Derives d'arylvinylether et leur utilisation comme herbicides

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GBGB9815508.8A GB9815508D0 (en) 1998-07-16 1998-07-16 New herbicidal compositions
GB9815508.8 1998-07-16
GB9816783.6 1998-07-31
GBGB9816783.6A GB9816783D0 (en) 1998-07-16 1998-07-31 New herbicidal compositions
GB9826903.8 1998-12-07
GBGB9826903.8A GB9826903D0 (en) 1998-07-16 1998-12-07 New herbicidal compositions

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001047863A3 (fr) * 1999-12-24 2002-05-02 Aventis Cropscience Sa Nouvelles compositions herbicides
JP2004537570A (ja) * 2001-08-10 2004-12-16 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 置換環状ケト−エノール系選択的除草剤および毒性緩和剤
US7547804B2 (en) 2002-07-15 2009-06-16 Myriad Genetics, Inc. Compounds, compositions, and methods employing same
CN102892290A (zh) * 2010-08-31 2013-01-23 明治制果药业株式会社 有害生物防除剂
CN103319421A (zh) * 2013-06-07 2013-09-25 常州大学 一种嘧啶水杨酸类除草剂嘧啶肟草醚的制备方法
EP3992178A4 (fr) * 2019-06-28 2023-10-04 Sumitomo Chemical Company, Limited Dérivé d'ester (méth)acrylique, et application et intermédiaire de production de celui-ci
CN118718018A (zh) * 2024-09-04 2024-10-01 吉林大学 一种复合载药平台及其制备方法和应用

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DE3904931A1 (de) * 1989-02-17 1990-08-23 Bayer Ag Pyridyl-substituierte acrylsaeureester
DE4019307A1 (de) * 1990-06-16 1991-12-19 Bayer Ag 2-methoximinocarbonsaeureester
FR2751642B1 (fr) * 1996-07-24 1998-09-11 Hoechst Schering Agrevo Sa Nouveaux derives de l'acide beta-methoxy acrylique, leur procede de preparation et leur application comme pesticides
BR9809746A (pt) * 1997-04-01 2000-06-20 Sumitomo Chemical Co Compostos de éteres oxìmicos, seu uso e intermediários para preparações dos mesmos.
DE19745376A1 (de) * 1997-10-14 1999-04-15 Bayer Ag Thiomide

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001047863A3 (fr) * 1999-12-24 2002-05-02 Aventis Cropscience Sa Nouvelles compositions herbicides
JP2004537570A (ja) * 2001-08-10 2004-12-16 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 置換環状ケト−エノール系選択的除草剤および毒性緩和剤
US7547804B2 (en) 2002-07-15 2009-06-16 Myriad Genetics, Inc. Compounds, compositions, and methods employing same
US8957214B2 (en) 2010-08-31 2015-02-17 Meiji Seika Pharma Co., Ltd. Pest control agent
AU2011297160B2 (en) * 2010-08-31 2014-11-20 Mitsui Chemicals Crop & Life Solutions, Inc. Noxious organism control agent
CN102892290A (zh) * 2010-08-31 2013-01-23 明治制果药业株式会社 有害生物防除剂
CN102892290B (zh) * 2010-08-31 2016-02-03 明治制果药业株式会社 有害生物防除剂
US9328068B2 (en) 2010-08-31 2016-05-03 Meiji Seika Pharma Co., Ltd. N-[1-((6-chloropyridin-3-yl) methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide for control of animal parasitic pests and agricultural/horticultural pests
US9717242B2 (en) 2010-08-31 2017-08-01 Meiji Seika Pharma Co., Ltd. N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide for control of agricultural/horticultural pests
US10085449B2 (en) 2010-08-31 2018-10-02 Meiji Seika Pharma Co., Ltd. N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2- trifluoroacetamide for control of agricultural/horticultural pests
CN103319421A (zh) * 2013-06-07 2013-09-25 常州大学 一种嘧啶水杨酸类除草剂嘧啶肟草醚的制备方法
EP3992178A4 (fr) * 2019-06-28 2023-10-04 Sumitomo Chemical Company, Limited Dérivé d'ester (méth)acrylique, et application et intermédiaire de production de celui-ci
US12082581B2 (en) 2019-06-28 2024-09-10 Sumitomo Chemical Company, Limited Acrylate derivative, use and production intermediate compound of the same
CN118718018A (zh) * 2024-09-04 2024-10-01 吉林大学 一种复合载药平台及其制备方法和应用

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