WO2014117677A1 - Composé contenant un hétérocycle n, s et ayant une action nématocide, procédé de préparation et utilisation - Google Patents

Composé contenant un hétérocycle n, s et ayant une action nématocide, procédé de préparation et utilisation Download PDF

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WO2014117677A1
WO2014117677A1 PCT/CN2014/071316 CN2014071316W WO2014117677A1 WO 2014117677 A1 WO2014117677 A1 WO 2014117677A1 CN 2014071316 W CN2014071316 W CN 2014071316W WO 2014117677 A1 WO2014117677 A1 WO 2014117677A1
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compound
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formula
alkyl
reaction
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徐晓勇
李忠
王高磊
李春燕
宋恭华
邵旭升
须志平
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East China University of Science and Technology
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    • 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
    • C07D417/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/34—Oxygen 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
    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/86—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
    • C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • the invention belongs to the field of pesticides.
  • the present invention relates to a compound containing a s-heterocyclic structure having nematicidal activity, a process for its preparation and use. Background technique
  • Plant parasitic nematodes are extremely harmful to plants. They can almost parasitize any part of the plant. They can cause mechanical damage to the host plants through feeding activities, and plunder the host plant's nutrition. Especially the esophageal gland secretions can cause host plants to occur. A series of pathological changes can also spread other pathogens or promote secondary infection of other pathogens, causing disease in host plants and causing yield loss. On a global scale, the harmfulness of plant parasitic nematodes is becoming more and more serious, which usually results in a 10 to 40% reduction in crop yields, and the annual economic losses are as high as 800 to 100 billion US dollars, which severely limits the development of the agricultural economy.
  • One of the objects of the present invention is to provide a novel chemical nematicide which is highly efficient, low in toxicity and highly selective, and a preparation method and application thereof.
  • Q is a substituted or unsubstituted d alkyl group, a C 2 - 6 alkenyl group, a C 2 - 6 block group, (: 3 - 7 cycloalkyl group, (: 5 - 7 cycloalkenyl group, phenyl group, naphthalene group) a ureido group, a ureido group, a thiourea group, a d alkyl-ureido group, an alkyl-thiourea group, a 5- or 6-membered heterocyclic ring or an 8- to 12-membered heteroaryl bicyclic ring system, said substituent being selected from the group consisting of One or more of the following groups: halogen, cyano, nitro, SF 5 , 0CN, SCN, R', OR', Si (R') 3 , NR'R", C (0) R,, C ( 0) OR', C (0) NR'R",
  • L is H, or a substituted or unsubstituted (6 alkyl, C 2 - 6 alkenyl, C 2 - 6 block basis, (: 3 - 7 -cycloalkyl, C 5 - 7 cycloalkenyl, phenyl, naphthyl Base, urea group, thiourea group, alkyl-ureido group, alkyl-thiourea group, 5- or 6-membered heterocyclic ring or 8 yuan to a 12-membered heteroaryl bicyclic ring system, the substituent being selected from one or more of the group consisting of: halogen, cyano, nitro, SF 5 , 0CN, SCN, R', OR', Si(R') 3 , NR'R",C(0)R', C(0) OR', C(0)NR'R",SR', S(0) m RS (0) 2 NR' R 0C(0) R 0C(0)NR' R OS (0) 2 R OS (0)
  • X and R are each independently cyano, nitro, trifluoromethyl, C(0)R', C(0)0R', C(0) set to 'R', S(0) or S(0) 2 set 'R';
  • ⁇ 11, 0, S or CH-R 3 , with the following conditions: When Y is H, Y is a single bond between adjacent C, and when Y is 0, S or CH-R 3 , Y And a double bond between adjacent C;
  • ⁇ is 11, 0, S or CH-R 3 , with the following conditions: When Z is H, Z is a single bond between adjacent C, and when Z is 0, S or CH-R 3 , Z And a double bond between adjacent C;
  • R', R" are each independently H, ( 6 fluorenyl, ( 6 haloalkyl, C 2 - 6 alkenyl, C 2 - 6 haloalkenyl, C 2 - 6 styl, C 2 - 6 halo block group, a substituted or unsubstituted (: 3 - cycloalkyl, (: 5--7 cycloalkenyl, phenyl, naphthyl, 5- or 6-membered heterocyclic or 8-12 yuan heteroaryl two a cyclic ring system, said substituent being selected from one or more of the group consisting of: halogen, cyano, nitro, SF 5 , 0CN, SCN, alkyl, d haloalkyl, C 2 - 6 alkenyl, C 2 - 6 haloalkenyl, C 2 - 6 block, C 2 - 6 halo block, hydroxy, hydroxy d- 4 alkyl, 0R 4 ,
  • ⁇ is alkyl, d haloalkyl, C 2 - 6 alkenyl, C 2 - 6 haloalkenyl, C 2 - 6 block, C 2 - 6 halo block, or substituted or unsubstituted C 3 - 7 cycloalkyl, (: 5 - 7 cycloalkenyl, phenyl, naphthyl, 5- or 6-membered heterocyclic or 8- to 12-membered heteroaryl bicyclic ring system, said substituent being selected from One or more of the following groups: halogen, cyano, nitro, SF 5 , 0CN, SCN, d alkyl, d haloalkyl, C 2 - 6 alkenyl, C 2 - 6 haloalkenyl, C 2 - 6- block, C 2 -6 halo block, 0R 4 , NR 4 R ⁇ C(0)R 4 , C(0)0R ⁇ C(0)NR 4 R 5 , SR
  • 1 is 11 , d alkyl, d haloalkyl, C 2 - 6 alkenyl, C 2 - 6 haloalkenyl, C 2 - 6 or C 2 - 6 halo block, or substituted or not substituted (: 3 - cycloalkyl, (: 5--7 cycloalkenyl, phenyl, naphthyl, 5- or 6-membered heterocyclic or 8-12 yuan bicyclic heteroaryl ring system, said substituents
  • the group is selected from one or more of the group consisting of: halogen, cyano, nitro, SF 5 , 0CN, SCN, ( 6 alkyl, ( 6 haloalkyl, C 2 - 6 alkenyl, C 2 - 6 haloolefin) Base, C 2 - 6 block, C 2 - 6 halo block, hydroxy, hydroxy d- 4 alkyl, 0R ⁇ NR 4 R ⁇ C(0)R 4
  • R 3 is a substituted or unsubstituted phenyl, naphthyl, 5- or 6-membered heterocyclic ring or an 8- to 12-membered heteroaryl bicyclic ring system, and the substituent is selected from one or more of the group consisting of: halogen , cyano, nitro, SF 5 , 0CN, SCN, alkyl, haloalkyl, C 2 - 6 alkenyl, C 2 - 6 haloalkenyl, C 2 - 6 block, C 2 - 6 halo block Base, hydroxy, hydroxy d- 4 alkyl, 0R 4 , NR 4 R 5 , C (0) R 4 , C (0) 0R ⁇ C (0) NR 4 R 5 , SR 4 , S (0) m R 7 , S (0) 2 NR 4 R 5 , 0C (0) R 7 , 0C (0) NR 4 R 5 , OS (0) 2 R 7 , 0
  • R 4 , R 5 and R 6 are each independently H, alkyl, d haloalkyl, C 2 - 6 alkenyl, C 2 - 6 haloalkenyl, C 2 - 6 Group or c 2 - 6 haloalkyl group blocks;
  • n is 0 or 1; preferably 0.
  • Q is a substituted or unsubstituted d- 6 alkyl, C 2 - 6 alkenyl group, a phenyl group, a naphthyl group, a thiourea group, a 5- or 6-membered heterocyclic or 8-12 yuan a heteroaryl bicyclic ring system, said substituent being selected from one or more of the group consisting of halogen, cyano, nitro, d- 4 fluorenyl, d- 4 haloalkyl, d- 4 alkoxy, amino , d- 4 alkylamino, d- 4 alkyl-carbonyl, ( 4 alkoxy-carbonyl, ( 4 alkylamino-carbonyl or phenylamino-carbonyl).
  • Q is a substituted or unsubstituted d- 6 alkyl, C 2 - 6 alkenyl group, a phenyl group, a naphthyl group, a thiourea group, thiazolyl, oxazolyl, thienyl, furyl group, Pyrrolyl, pyrazolyl, tetrahydrofuranyl, pyridyl, pyrimidinyl, 1,2,3-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-oxadiazolyl, benzene And furyl, benzothienyl, fluorenyl, quinolyl, isoquinolyl, oxazolyl, benzo[c]thiazolyl, benzo[c]oxazolyl, benzo[c][1 , 2, 3]thiadiazolyl, imidazo[1,2-a]pyridyl, quinazolinyl, quinox
  • the substituent is selected from one or more of the group consisting of: halogen, nitro, d- 4 alkyl, d- 4 haloalkyl, d- 4 alkoxy, amino, d- 4 alkane Amino, d- 4 alkyl-carbonyl, d- 4 alkoxy-carbonyl, d- 4 alkylamino-carbonyl or phenylamino-carbonyl.
  • Q is a substituent selected from one or more selected from the group consisting of halogen, nitro, d- 4 haloalkyl, d- 4 alkoxy, and phenylamino-carbonyl.
  • L is H, or substituted or unsubstituted d- 6 alkyl, C 2 - 6 alkenyl group, a phenyl group, a naphthyl group, a thiourea group, a 5- or 6-membered heterocyclic ring or an 8- To a 12-membered heteroaryl bicyclic ring system, the substituent is selected from one or more of the group consisting of: halogen, cyano, nitro, d- 4 alkyl, d- 4 haloalkyl, d- 4 alkoxy Alkyl, amino, d- 4 alkylamino, d- 4 alkyl-carbonyl, ( 4 alkoxy-carbonyl, ( 4 alkylamino-carbonyl or phenylamino-carbonyl).
  • 11 ⁇ 1, a substituted or unsubstituted d- 6 alkyl, C 2 - 6 alkenyl group, a phenyl group, a naphthyl group, a thiourea group, thiazolyl, oxazolyl, thienyl, Furanyl, pyrrolyl, pyrazolyl, tetrahydrofuranyl, pyridyl, pyrimidinyl, 1,2,3-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-oxadiazole Benzofuranyl, benzothienyl, fluorenyl, quinolyl, isoquinolyl, oxazolyl, benzo[c]thiazolyl, benzo[c]oxazolyl, benzo[c ] [1,2, 3]thiadiazolyl, Imidazo[1,2-a]pyridinyl, quinazolinyl, quinoxalin
  • L is H or a phenyl group substituted by one or more substituents selected from the group consisting of halogen, cyano, nitro, d- 4 haloalkyl or d- 4 alkoxy. In another preferred example, .
  • X and R are each independently cyano, nitro, trifluoromethyl, C(0)0R', C(0)NR'R", trifluoroacetyl or trifluoromethanesulfonate.
  • Acyl group is independently cyano, nitro, trifluoromethyl, C(0)0R', C(0)NR'R", trifluoroacetyl or trifluoromethanesulfonate.
  • X is cyano or C(0)0R' ; preferably cyano.
  • R is cyano, C(0)0R' or C(0)NR'R"; preferably C(0)0R'.
  • X is cyano; R is C(0)0CH 3 or C(0)NH 2 .
  • R 3 is a substituted or unsubstituted phenyl, naphthyl, 5- or 6-membered heterocyclic ring or an 8- to 12-membered heteroaryl bicyclic ring system, and the substituent is selected from the group consisting of One or more of: halogen, cyano, nitro, d- 4 alkyl, d- 4 haloalkyl, hydroxy, hydroxy d- 4 alkyl, ( 4 alkoxy, amino, ( 4 alkylamino, D- 4 alkyl-carbonyl or ( 4- methoxy-carbonyl).
  • R 3 is substituted or unsubstituted phenyl, naphthyl, thiazolyl, oxazolyl, thienyl, furyl, pyrrolyl, pyrazolyl, pyridyl, pyrimidinyl, 1,2 , 3-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-oxadiazolyl, benzofuranyl, benzothienyl, fluorenyl, quinolinyl, isoquinoline Boryl, carbazolyl, benzo[c]thiazolyl, benzo[c]oxazolyl, benzo[c][1,2,3]thiadiazolyl, imidazo[1,2-a] Pyridyl, quinazolinyl, quinoxalinyl, porphyrinyl, pyridazinyl, 1,8-naphthyridinyl, or benzo[ ⁇ ][1,2,3]triazine
  • R 3 is a substituted or unsubstituted phenyl, thienyl, furyl, pyrrolyl, pyridyl group, and the substituent is selected from the group consisting of a d- 4 haloalkyl group or d- 4 Alkoxy. In another preferred embodiment, R 3 is
  • the compound includes the compound shown in Table 2.
  • an agricultural composition comprising:
  • (b) agriculturally acceptable carriers and/or excipients O. 05-90 ⁇ % ⁇
  • the composition of the total weight of the agricultural composition is 0. 01-99. 9% by weight; preferably 0. 05-90% by weight.
  • a third aspect of the invention there is provided the use of the agricultural composition according to the second aspect of the invention for killing or preventing parasitic nematodes of agricultural and forestry plants; or for killing or preventing parasitic nematodes of agricultural and forestry plants Nematicide composition.
  • the agricultural composition further comprises other active substances selected from the group consisting of nematicides, insecticides, baits, fungicides, acaricides, fungicides Or growth control agent.
  • the plant parasitic nematode is a root knot nematode, a cyst nematode, a tumor nematode, a stem and a leaf nematode, a nematode or a pine wood nematode.
  • the plant parasitic nematode is a southern root knot nematode.
  • a compound according to the first aspect of the invention an optical isomer, a cis or a pharmaceutically acceptable salt thereof, or a combination thereof, for use For preparing a nematicide composition.
  • a compound of the formula (I) according to the first aspect of the invention, an optical isomer thereof, a cis-trans isomer or an agrochemically acceptable
  • the method for preparing a salt comprises the steps of: first reacting a compound of the formula A with a compound of the formula B in an inert solvent in the presence of a base, and then reacting with a compound of the formula C (the compound of the formula C is C1C (Y) (C3 ⁇ 4) n C (Z) Cl or BrC (Y) (C3 ⁇ 4) n C (Z) Br) reacts to form a compound of formula (I):
  • a compound of formula A is first reacted with a compound of formula B in the presence of a base in an inert solvent to form a reaction mixture; and the resulting reaction mixture is then reacted with a compound of formula C to form a compound of formula (I).
  • reaction is carried out at 0 to 60 ° (: preferably; at 20 to 40 ° (: in another preferred embodiment,
  • the process comprises the step (a): first reacting a compound of the formula A with a compound of the formula B in an inert solvent in the presence of a base, and then reacting with a compound of the formula C1 to form a compound of the formula (II):
  • the method comprises the step (b): first reacting a compound of the formula A with a compound of the formula B in an inert solvent in the presence of a base, and then reacting with a compound of the formula C2 to form a compound of the formula (III):
  • the method comprises the step (c): firstly, a compound of the formula A and a compound of the formula B compound (IV) in the presence of a base in an inert solvent:
  • the process comprises the step (d): reacting a compound of formula (III) with a compound of formula D in an inert solvent to form a compound of formula (V):
  • the step (a) is: first reacting a compound of the formula A with a compound of the formula B in an inert solvent in the presence of a base to form a reaction mixture; and then reacting the obtained reaction mixture with The compound of formula C1 is reacted to form a compound of formula ( ⁇ ).
  • the step (b) is: first reacting a compound of the formula A with a compound of the formula B in an inert solvent in the presence of a base to form a reaction mixture; and then reacting the obtained reaction mixture with the formula The C2 compound is reacted to form a compound of formula (III).
  • the step (c) is: first reacting a compound of the formula A with a compound of the formula B in an inert solvent in the presence of a base to form a reaction mixture; and then reacting the obtained reaction mixture with the formula The C3 compound is reacted to form a compound of formula (IV).
  • the base is selected from one or more of the group consisting of: triethylamine, diisopropylethylamine, diethylamine, piperidine, piperazine, morpholine, N-methyl Morpholine, triethylenediamine (DAB0C), 1, 8-diazabicyclo [5. 4. 0] undec-7-ene (DBU), 1,5-diazabicyclo[4. 3. 0] ⁇ -5-ene (08 ⁇ , potassium carbonate, potassium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, sodium methoxide or sodium ethoxide.
  • the base is selected from the group consisting of triethylamine, diisopropylethylamine, cesium carbonate, sodium hydroxide or potassium hydroxide; preferably potassium hydroxide.
  • the inert solvent is selected from the group consisting of methanol, acetonitrile, N,N-dimethylformamide, 1,4-dioxane, benzene or toluene; preferably N, N -dimethylformamide.
  • the step (a) is: first reacting a compound of the formula A with a compound of the formula B in an inert solvent at 20 to 40 ° C in the presence of potassium hydroxide to form a reaction. The mixture is then reacted with a compound of formula C1 at 50 to 60 ° C to form a compound of formula (II).
  • the step (b) is: first reacting a compound of the formula A with a compound of the formula B in an inert solvent at 20 to 40 ° C in the presence of potassium hydroxide to form a reaction. The mixture is then reacted with a compound of formula C2 to form a compound of formula (III).
  • the step (c) is: first reacting a compound of the formula A with a compound of the formula B in an inert solvent at 20 to 40 ° C in the presence of potassium hydroxide to form a The reaction mixture; and the obtained reaction mixture is then reacted with a compound of the formula C3 to form a compound of the formula (IV).
  • the step (d) is: reacting a compound of the formula (III) with a compound of the formula D in an inert solvent at 20 to 40 ° C under the catalysis of triethylamine. Thereby a compound of formula (V) is formed.
  • reaction mixture obtained by reacting the compound of the formula A with the compound of the formula B contains an intermediate product which is a salt of the anionic compound represented by the formula (VI) and a base:
  • the content of the intermediate product is 10-99.99 wt; preferably 20-90 wt ; more preferably 50- 80 wt %.
  • a nematicidal and/or nematode-resistant method comprising the steps of: applying the compound of the first aspect of the invention or the composition of the second aspect to suffering Or plants that may be exposed to nematodes, the soil around them, or the environment.
  • a process for the preparation of the agricultural composition of the second aspect of the invention comprising the steps of: (a) the compound of the first aspect of the invention, optical isomerism thereof The physicochemical, cis-trans isomer or agrochemically acceptable salt, or a combination thereof; is mixed with (b) a pesticidally acceptable carrier and/or excipient to form the agricultural composition.
  • d alkyl refers to a straight or branched alkyl group having from 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert. Butyl, or the like.
  • C 2 - 6 alkenyl refers to a straight or branched alkenyl group having 2 to 6 carbon atoms, such as ethenyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, or the like.
  • C 2 - 6 block refers to a straight or branched block group having 2 to 6 carbon atoms, such as an ethyl group, a propyl group, or the like.
  • (: 3--7 cycloalkyl means a cyclic alkyl group having 3-7 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or the like.
  • the term "(: 5--7 cycloalkenyl” means having 5-7 carbon atoms, cyclic alkenyl groups one or more double bond, for example cyclopentenyl, cyclohexenyl, cycloheptenyl, 1, 3-cyclohexadienyl, 1, 4-cyclohexadienyl, or the like.
  • V 4 alkoxy refers to a straight or branched alkoxy group having from 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, butyl Oxyl, isobutoxy, sec-butoxy, tert-butoxy, or the like.
  • halogen means fluoro, chloro, bromo, or iodo.
  • halogenated refers to a group substituted by the same or different one or more of the above halogen atoms, such as a trifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, or the like.
  • ring or “ring system” refers to a carbocyclic or heterocyclic ring.
  • heterocycle means that at least one of the atoms forming the heterocyclic backbone is not carbon and is nitrogen, oxygen or sulfur. Typically, the heterocycle contains no more than 4 nitrogens, no more than 2 oxygens, and/or no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated or fully unsaturated ring.
  • ring system refers to a fused ring in which two or more rings are joined together.
  • the term "5- or 6-membered heterocyclyl” refers to a five- or six-membered ring containing one or more heteroatoms selected from nitrogen, oxygen or sulfur, such as pyridinyl, thiazolyl, thienyl, furan. , pyrrolyl, pyrazolyl, pyrimidinyl, tetrahydrofuranyl, oxazolyl, 1,2,3-thiadiazolyl, 1,3,4-thiadiazolyl, or 1, 3, 4-oxo Azolyl and the like.
  • heterocyclic ring system means a ring system in which at least one ring in the ring system is a heterocyclic ring.
  • heteromatic ring system refers to a system in which at least one ring in the ring system is an aromatic ring.
  • the term "8- to 12-membered heteroaryl bicyclic ring system” includes benzofuranyl, benzothienyl, indenyl, quinolyl, isoquinolinyl, oxazolyl, benzo[c Imidazolyl, benzo[c]thiazolyl, benzo[c]oxazolyl, benzo[c][1,2,3]thiadiazolyl, imidazo[1,2-a]pyridinyl, Quinazolinyl, quinoxalinyl, porphyrinyl, pyridazinyl, 1,8-naphthyridinyl, or benzo[c][1,2,3]triazin-4(3H)-3-yl Wait.
  • the groups described in the present invention may be substituted with a substituent selected from the group consisting of halogen, nitrile group, nitro group, hydroxyl group, amino group, unless otherwise specified as "substituted or unsubstituted".
  • d alkyl-amino, d alkyl, C 2 -6 alkenyl, C 2 - 6 block, ( 6 alkoxy, halo ( 6 alkyl, halo C 2 - 6 alkenyl, halogen C 2--6 block basis, halo (6 alkoxy group, an allyl group, ⁇ , phenyl, Institute of Cl- 6-Cl-6 alkoxy group homes, homes of Cl- 6 alkoxy - carbonyl, phenoxycarbonyl , C 2 - 6 alkynyl group - carbonyl group, C 2 - 6 alkenyl - carbonyl group, C 3 - 6 cycloalkyl - carbonyl, d- 6 alkyl - sulfonyl group, a benzoyl group, a furyl carbonyl group or N, N- two a methylaminocarbonyl group, or one or more selected from the group consisting of halogen, d- 6 haloal
  • the compounds of the invention may contain one or more asymmetric centers and thus occur in the form of racemates, racemic mixtures, single enantiomers, diastereomeric compounds and single diastereomers.
  • the asymmetric center that can exist depends on the nature of the various substituents on the molecule. Each such asymmetric center will independently produce two optical isomers, and all possible optical isomers and diastereomeric mixtures and pure or partially pure compounds are included within the scope of the invention. This hair It includes all isomeric forms of the compound. Nematicidal activity of the active substance of the invention
  • active substance of the present invention or “active compound of the present invention” means a compound of the structure represented by the formula (I), an optical isomer thereof, a cis-trans isomer or a pesticide-acceptable salt. Its heterocyclic structure containing N and S has remarkable nematicidal activity, and the nematicidal spectrum is broad and stable.
  • agrochemically acceptable salt means that the anion of the salt is known and acceptable in forming a pharmaceutically acceptable salt of a nematicide.
  • the salt is water soluble.
  • the acid addition salts formed from the compounds of formula (I) include salts of mineral acids, such as hydrochlorides, phosphates, sulfates, nitrates; and salts comprising organic acids, such as acetates, Benzoate.
  • the active substance of the present invention can be used as a control and elimination of a wide range of agroforestry plant parasitic nematodes.
  • nematocide is a general term for substances having the action of controlling all plant parasitic nematodes mentioned herein.
  • plant-parasitic nematodes include, but are not limited to, root-knot nematodes, such as peanut root-knot nematodes (fe ii ⁇ T/ ⁇ arenaria), root-knot nematode ⁇ Meloidogyne chitwoodi, short-rooted nematode ⁇ Meloidogyne exigua), north Meloidogyne hapla, Meloidogyne incognita, Maloca knotworm Cystic nematodes, such as ⁇ ce 3 ⁇ 4 rostochiensis 3 ⁇ 4 3 ⁇ 4 ⁇ ⁇ A ( Globodera pallida), tobacco stalk nematode ( owcera tabacum ) , and other cyst nematodes ( owcers ) ; heterologous nematodes , such as grosporium ⁇ e ei era a venae, ⁇ e ei era glycines
  • elegans such as the genus ara j ⁇ eflcAis; root rot nematodes, Shortest tail short body line Coffee) Short-horned nematode ⁇ Pra tylenchus zeae) puncture of short penetulae (ra pene trans) and other short-living nematodes ⁇ Pratylenchus); perforated nematodes, such as banana perforated nematodes (73 ⁇ 4 ⁇ 3 ⁇ 4 ⁇ £ ⁇ 5 s ffl ' ) and others Radopholus Nematode, such as the kidney-shaped nematode (73 ⁇ 4 tylenchus robus tus) and other nematodes ⁇ Rotylenchus), such as the original burrowing nematode ( > c oo3 ⁇ 4i3 ⁇ 4s/?r ffl i /s And other burr-worms, Trichodorus dwarf nemato
  • the compounds of the present invention have a particularly good control effect against Meloidogyne® c 0 3 ⁇ 47® ia.
  • Nematicide composition containing active substance of the present invention is a particularly good control effect against Meloidogyne® c 0 3 ⁇ 47® ia.
  • the active substance of the present invention can be prepared into a nematicidal composition in a conventional manner.
  • These active compounds can be formulated into conventional preparations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active substances, in polypolymers Microcapsules in the product, coating compositions for seeds, and preparations for use with burning devices, such as smoked cartridges, smoked cans and smokers, and ULV cold mist and hot fog (Warm) Mist) [J.
  • compositions can be produced by known methods, for example, by mixing the active compound with an extender, which is a liquid or liquefied gas or solid diluent or carrier, and optionally a surfactant, an emulsifier and/or A dispersant and/or a foam former.
  • an extender which is a liquid or liquefied gas or solid diluent or carrier
  • a surfactant for example, an organic solvent can also be used as an auxiliary.
  • an organic solvent can also be used as an auxiliary.
  • a liquid solvent When a liquid solvent is used as a diluent or carrier, it is basically suitable, such as: aromatic hydrocarbons such as xylene, toluene or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride Or methylene chloride; aliphatic hydrocarbons such as cyclohexane or paraffin, such as mineral oil fractions; alcohols such as ethanol or ethylene glycol and their ethers and lipids; ketones such as acetone, methyl ethyl ketone, methyl isobutyl Ketone or cyclohexanone; or less common polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatic hydrocarbons such as xylene, toluene or alkylnaphthalene
  • chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride
  • the diluent or carrier of the liquefied gas refers to a liquid which will become a gas at normal temperature and pressure, such as an aerosol propellant such as a halogenated hydrocarbon and butane, propane, nitrogen and carbon dioxide.
  • the solid carrier may be ground natural minerals such as kaolin, clay, talc, quartz, activated clay, montmorillonite, or diatomaceous earth; and ground synthetic minerals such as highly dispersed silicic acid, alumina And silicates.
  • the solid carrier for the granules is ground and graded natural zircon, such as calcite, marble, pumice, sepiolite and dolomite, as well as inorganic and organic coarse powder synthetic particles, and organic materials such as sawdust, coconut shell, Corn cobs and granules of tobacco stems.
  • Emulsified columns of nonionic and anionic agents can be used as emulsifiers and/or foam formers.
  • polyoxyethylene-fatty acid esters polyoxyethylene-fatty alcohol ethers, such as alkaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonic acids Esters and albumin hydrolysates.
  • Dispersing agents include lignin sulfite waste liquors and methylcellulose.
  • Binders such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or emulsions such as gum arabic, polyvinyl alcohol and polyvinyl acetate may be used in the formulation.
  • Colorants such as inorganic dyes such as iron oxide, oxidized diamond and Prussian blue; organic dyes such as azo dyes or metal phthalocyanine dyes; and trace nutrients such as iron, manganese, boron, copper, cobalt, aluminum may be used. And zinc salts, etc.
  • the active compounds of the present invention may be formulated as a mixture with other active compounds in their commercial preparations or in the dosage forms prepared from these preparations.
  • These other active compounds are nematicides, insecticides, fungicides, Fungicides, growth control agents, and the like.
  • Nematicides include, for example, phosphates, carbamates, chlorinated hydrocarbons, and substances produced by microorganisms such as avermectin.
  • the active compounds of the invention may also be formulated as a mixture with synergists in their commercial preparations or in the dosage forms prepared from these preparations, which are compounds which increase the action of the active compound, The compound itself is active, and it is not necessary to add a synergist.
  • the total weight of the nematicide composition is 0. 001-99.
  • the concentration of the active compound in a commercial preparation or a dosage form can vary within a wide range.
  • the concentration of the active compound in the dosage form may be from 0. 0000001-100% (g/v), preferably between 0.0001 and 1% (g/v).
  • the compound of the formula (I) of the present invention can be produced by the following method, however, the conditions of the method, such as the reactant, the solvent, the base, the amount of the compound used, the reaction temperature, the time required for the reaction, and the like are not limited to the following explanations. .
  • the compounds of the present invention may also be conveniently prepared by combining various synthetic methods described in the specification or known in the art, and such combinations are readily made by those skilled in the art to which the present invention pertains.
  • each reaction is usually carried out in an inert solvent at a reaction temperature of 0 to 60 ° C (preferably 20 to 40 ° C).
  • the reaction time is usually 2 to 24 h, preferably 4 to 12 ho.
  • the base used in the reaction includes, but is not limited to, triethylamine, diisopropylethylamine, diethylamine, piperidine, piperazine, morpholine, N-methylmorpholine, triethylenediamine ( DAB0C), 1, 8-diazabicyclo[5. 4. 0] ⁇ -carbon_7-ene (DBU), 1, 5-diazabicyclo[4. 3. 0] ⁇ -5- Alkene (DBN), potassium carbonate, potassium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, or a combination thereof.
  • the starting compound of the present invention can be synthesized by a method comprising the following steps:
  • L and Q are as defined above;
  • a compound of the formula E, triethylenediamine and carbon disulfide is reacted in an inert solvent (e.g., acetone) at a temperature (e.g., 20 to 40 ° C) to obtain a yellow solid compound of formula F.
  • an inert solvent e.g., acetone
  • a compound of the formula F and bis(trichloromethyl)carbonate are reacted in an inert solvent (e.g., chloroform) at a temperature (e.g., 20 to 40 ° C) to give a colorless liquid compound of formula A.
  • an inert solvent e.g., chloroform
  • the method comprises the steps of:
  • the method of the present invention synthesizes:
  • L, Q, X and R are as defined above, and n is an integer of 0-3;
  • the obtained reaction mixture is then reacted with a compound of the formula C1 at a certain temperature (e.g., 50 to 60 ° C) for a period of time (e.g., 2 to 10 hours) to obtain a compound of the formula (II).
  • a certain temperature e.g., 50 to 60 ° C
  • a period of time e.g., 2 to 10 hours
  • the reaction solution is poured into ice water, and the precipitated solid is recrystallized to obtain a compound of the formula ( ⁇ ).
  • the obtained reaction mixture is then reacted with a compound of the formula C2 at a certain temperature (e.g., 20 to 40 V) for a period of time (e.g., 5 to 12 hours) to obtain a compound of the formula (III).
  • a certain temperature e.g. 20 to 40 V
  • a period of time e.g. 5 to 12 hours
  • the reaction liquid is poured into ice water, and the precipitated solid is recrystallized to obtain a compound of the formula (III).
  • the resulting reaction mixture is then reacted with a compound of formula C3 at a temperature (eg, 20 to 40 V) for a period of time (eg,
  • the reaction liquid is poured into ice water, and the precipitated solid is recrystallized to obtain a compound of the formula (III).
  • the compound of the formula (V) can be synthesized by the following method:
  • L, Q, X, R and R 3 are as defined above, and n is an integer from 0 to 3;
  • the X intermediate product is a salt of an anionic compound represented by the formula (VI) with a base: Q , tr e (vi), for example, a salt of the compound of the formula (VI) and potassium hydroxide is 1 " Q A' SK
  • the intermediate product is contained in an amount of 10 to 99.99 wt ; preferably 20 to 90 wt ; more preferably 50 to 80 wt%.
  • biphenylisothiocyanate was similar to the synthesis of 2-fluorophenyl isothiocyanate in Example 1, except that benzidine was used in place of 2-fluoroaniline.
  • 2-fluoro-2'-nitrobiphenyl isothiocyanate is similar to the procedure of Example 5.2 of Example 5 except that 2-fluoro-2'-nitrobenzidine is used in place of benzidine.
  • the preparation of 2-fluoro-2'-nitrobenzidine was similar to that of Example 5.1, except that 4-iodo-2-fluoroaniline was used in place of 4-iodoaniline, and 2-nitrophenylboronic acid was used in place of phenylboronic acid. .
  • 2-fluoro-3'-nitrobiphenyl isothiocyanate is similar to the procedure of Example 5.2 of Example 5 except that 2-fluoro-3'-nitrobenzidine is used in place of benzidine.
  • the preparation of 2-fluoro-3'-nitrobenzidine was similar to that of Step 5.1 of Example 5, except that 4-iodo-2-fluoroaniline was used in place of 4-iodoaniline, and 3-nitrophenylboronic acid was used in place of phenylboronic acid. .
  • the preparation method of 2 6-difluoro-2'-methoxybiphenyl isothiocyanate is similar to that of the step 5.2 of Example 5, except that the 6 6-difluoro-2'-methoxy group is used.
  • Aniline replaces benzidine.
  • the preparation of 2 6-difluoro-2'-methoxybenzidine is similar to that of step 5.1 of Example 5, except that 4-iodo-2 6-difluoroaniline is used instead of 4-iodoaniline, 2-methoxy
  • the phenyl boronic acid replaces the phenylboronic acid.
  • the preparation method of 2 6-difluoro-3'-methoxybiphenyl isothiocyanate is similar to that of the step 5.2 of Example 5, except that the 6 6-difluoro-3'-methoxy group is used.
  • Aniline replaces benzidine.
  • the preparation of 2 6-difluoro-3'-methoxybenzidine is similar to that of step 5.1 of Example 5, except that 4-iodo-2 6-difluoroaniline is used instead of 4-iodoaniline, 3-methoxy
  • the phenyl boronic acid replaces the phenylboronic acid.
  • the preparation method of 2-fluoro-2'-methoxybiphenyl isothiocyanate is similar to that of the step 5.2 of Example 5, except that 2-fluoro-2'-methoxybenzidine is used instead of benzidine. .
  • the preparation of 2-fluoro-2'-methoxybenzidine was similar to that of Step 5.1 of Example 5, except that 4-iodo-2-fluoroaniline was used instead of 4-iodoaniline, and 2-methoxyphenylboronic acid was used instead. Phenylboronic acid.
  • the method for producing 5-mercaptoisothiocyanate was similar to the step 1.1 of Example 1, except that 5-aminoaniline was used instead of 2-fluoroaniline.
  • reaction mixture was poured into ice water, and a yellow solid was crystallized, filtered, ethyl acetate crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals crystals 23 2-(1-Cyano-1-carboxylic acid methyl ester)-3-N-(5-benzo[ ⁇ /][1 2 3]thiadiazolyl)-1,3-thiazine
  • the preparation method of 5-benzo[d[3 2]thiadiazolyl isothiocyanate is similar to the step 1.1 of Example 1, except that 5-aminobenzo[ ⁇ /][1 2 3 Thiacazole instead of 2-fluoroaniline.
  • the preparation method of 5-imidazo[l 2-a]pyridyl isothiocyanate is similar to that of step 1.1 of Example 1, except that 5-aminoimidazo[l2-a]pyridine is used instead of 2-fluoro aniline.
  • Root-knot nematode belongs to the genus Nematode, i ylenchid ), suborder, genus, genus ⁇ Heteroderidea), root-knot nematode (fe ci3 ⁇ 4T/7 /7ae), root-knot nematode, is a hazard Serious plant parasitic nematodes.
  • the southern root-knot nematode (fe ⁇ o c ⁇ T/ ⁇ c a) was used as the test object, and the cucumber seedlings were used as the test host, and the test tube method was used for testing.
  • the sample to be tested is prepared into a drug solution at the required concentration, and a sufficient amount of root-knot nematode second instar larvae is prepared. After planting a one-week-old cucumber seedling into a test tube, an appropriate amount of the prepared liquid was added to the test tube, and about 2000 larvae were inserted into each test tube.
  • the test tubes were cultured at 20 25 ° C for 10 h, and after 20 d, the number of roots on the roots of each plant was counted. Each sample was tested 3 times, and each sample was subjected to 4 replicates per test.
  • Distilled water was used as a blank control, distilled water plus root-knot nematode was used as a negative control, and phenylphosphinus and avermectin solutions were used as positive controls.
  • Inhibition rate (%) (negative control score - test group score) / negative control score X 100%
  • the following components were prepared in proportion: 65.0% of any of the compounds II-1 to V-36 (Table 2); 2.0% dodecylphenol polyglycol ether; 4.0% sodium lignosulfonate; 6.0% Sodium aluminum silicate; 23.0% montmorillonite (calcined).

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  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
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  • Pest Control & Pesticides (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un composé contenant un hétérocycle N, S et ayant une action nématocide, un procédé de préparation et son utilisation. L'invention concerne plus précisément un composé de la formule (I), ou un isomère optique, des cis/trans isomères ou un sel acceptable en agrochimie de celui-ci, ainsi qu'un procédé de préparation. L'invention concerne également une composition à vocation agricole contenant le composé, ainsi que les utilisations de cette composition à vocation agricole. Le composé possède une excellente activité nématocide.
PCT/CN2014/071316 2013-01-31 2014-01-24 Composé contenant un hétérocycle n, s et ayant une action nématocide, procédé de préparation et utilisation Ceased WO2014117677A1 (fr)

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CN104447265B (zh) * 2014-12-05 2016-08-24 中国科学院昆明植物研究所 醌类化合物及其制备方法与其用作为杀线虫农药
CN104530037B (zh) * 2015-01-21 2020-12-18 华东理工大学 一种具有杀线虫活性的三嗪杂环化合物及其制法和用途
CN112279794A (zh) * 2020-10-29 2021-01-29 江苏创拓新材料有限公司 一种异硫氰酸酯类液晶单体的合成方法

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