USRE38188E1 - Ethylene derivatives and pesticides containing said derivatives - Google Patents

Ethylene derivatives and pesticides containing said derivatives Download PDF

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USRE38188E1
USRE38188E1 US09/983,477 US98347701A USRE38188E US RE38188 E1 USRE38188 E1 US RE38188E1 US 98347701 A US98347701 A US 98347701A US RE38188 E USRE38188 E US RE38188E
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group
optionally substituted
alkyl
phenyl
alkyl group
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US09/983,477
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Tomoyuki Ogura
Hiroshi Murakami
Akira Numata
Rika Miyachi
Toshiro Miyake
Norihiko Mimori
Shinji Takii
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Nissan Chemical Corp
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Nissan Chemical Corp
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    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/82—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 three ring hetero 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
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • C07D231/16—Halogen atoms or nitro radicals
    • 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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • 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

Definitions

  • the present invention relates to novel ethylene derivatives, and also to agricultural chemicals and agents for preventing the attachment of aquatic organisms containing said derivatives as an active ingredient.
  • the agricultural chemicals as referred to herein include insecticides, acaricides, nematocides, herbicides and fungicides, etc., and are especially pesticides in the field of agriculture, horticulture, stock farming and sanitation.
  • the agent for preventing the attachment of aquatic organisms are chemicals for preventing the attachment of harmful aquatic organisms such as shells and algae to fishing nets, the bottoms of ships, marine equipment such as buoys, marine constructions, circulating water systems in thermal and atomic power plants, inlet channels for heat exchanger cooling water in chemical industry, underwater constructions and reservoirs.
  • Japanese Patent Application Laid-Open No. Sho 53-92769 discloses the use of 2′-chloro-3-hydroxy-2-(4-phenyl-2-thiazolyl)-cinnamoyl nitrile as an insecticide; and International Patent Application Laid-Open No. WO-95/29591 discloses its use as an aquatic adhesion inhibitor.
  • Japanese Patent Application Laid-open No. Sho 60-11452 discloses the use of 2-(4-chlorophenyl)-3-(3-pyridyl)-3-oxopropionitrile as a herbicide and Japanese Patent Application Laid-open No. Sho 60-11401 discloses its use as a fungicide.
  • antifouling coatings comprising organic tin compounds such as bis(tributyltin) oxide or copper compounds such as copper sulfate and cuprous oxide.
  • organic tin compounds are highly toxic, though being effective in preventing the adhesion of aquatics, and are especially prone to accumulate in the bodies of fishes and shellfishes. As so promoting the environmental pollution, the use of those compounds is now under legal controls.
  • Copper compounds are widely used in antifouling coatings for inlet channels and for the bottoms of ships. However, like tin compounds, copper compounds contain a copper as a heavy metal.
  • the present inventors have assiduously studied to develop agricultural chemicals and agents for preventing the attachment of aquatic organisms which can exhibit excellent pesticidal activities even when used in small amounts, and which have few negative influences on non-targeted organisms such as mammals, fishes and useful insects, and, as a result, have found that the compounds mentioned hereinunder are highly safe and have excellent pesticidal activities and activities for preventing the attachment of aquatic organisms.
  • the present inventors have completed the present invention.
  • the present invention provides the following [1] to [25]
  • Q represents a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl, pyra
  • A represents a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolin
  • A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrimidinyl,
  • A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazin
  • A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl,
  • A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, is
  • A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyrida
  • B represents H, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkoxyalkyl group, CH 3 SCH 2 , CH 3 OC 2 H 4 OCH 2 , a C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 1 -C 4 alkyl group substituted by a benzoyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a tetrahydropyranyl group, (CH 3 ) 3 Si, a C 1 -C 4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, —SO 2 CF 3 , a C 1 -C 4
  • B is a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkoxyalkyl group, CH 3 SCH 2 , CH 3 OC 2 H 4 OCH 2 , a C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 1 -C 4 alkyl group substituted by a benzoyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a tetrahydropyranyl group, (CH 3 ) 3 Si, a C 1 -C 4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a tetrahydropyranyl group, (CH 3 ) 3
  • E represents a heterocyclic group optionally substituted by a C 1 -C 4 alkyl or C 1 -C 4 haloalkyl group—(said heterocyclic group being a 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,3,4-oxadiazol-2-yl, 5-tetrazolyl, 2-oxazolinyl or 1,2,4,5-tetrazin-3-yl group) - or represents a halogen, a C 2 -C 4 alkynyl group, a phenylethynyl group optionally substituted by Z, a C 1 -C 4 haloalkyl group, CN, an isonitrile group, NO 2 , N 3 , CHO, a C 2 -C 5 alkylcarbonyl group, a C 2 -C
  • G is a substituent freely selected from a halogen atom, a C 1 -C 10 alkyl group, a C 2 -C 4 cyanoalkyl group, a C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 2 -C 4 alkenyl group, a C 2 -C 6 alkynyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 halocycloalkyl group, a C 3 -C 6 cycloalkyl group optionally substituted by a C 1 -C 3 alkyl group, a C 1 -C 10 alkoxy group, a C 2 -C 6 alkenyloxy group, a C
  • R is a substituent freely selected from a halogen atom, a C 1 -C 10 alkyl group, a C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 2 -C 8 alkenyl group, a C 2 -C 6 alkynyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 halocycloalkyl group, a C 3 -C 6 cycloalkyl group optionally substituted by a C 1 -C 3 alkyl group, a C 1 -C 6 alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkynyloxy group, a C
  • Y is a substituent freely selected from a halogen atom, a C 1 -C 10 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkynyloxy group, a C 1 -C 4 haloalkoxy group, a C 2 -C 6 haloalkenyloxy group, a C 2 -C 6 haloalkynyloxy group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a C 2 -C 6 alkenylsulfenyl group, a C 2 -C 6 alkenylsulfinyl group, a C 2 -C 6 alkenyls
  • W is a substituent freely selected from a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a C 1 -C 4 haloalkylsulfenyl group, a C 1 -C 4 haloalkylsulfinyl group, a C 1 -C 4 haloalkylsulfonyl group, a C 2 -C 4 alkenyl group, a C 2 -C 4 haloalkenyl group, a C 2 -C 4 alkenyloxy group, a C 2 -C 4 hal
  • T 1 represents a C 1 -C 20 alkyl group, a C 2 -C 6 alkenyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 4 alkoxy-C 1 -C 4 alkyl group, a C 3 -C 6 halocycloalkyl group, a C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 3 -C 6 cycloalkyl group optionally substituted by a C 1 -C 3 alkyl group, a cycloalkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 3 alkyl group, a cyclopropyl group substituted by both a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group and
  • T 2 and T 3 each independently represent OH, a phenyl group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, or a C 1 -C 4 alkylsulfenyl group;
  • T 4 , T 6 and T 8 each independently represent H, a C 1 -C 6 alkyl group, a C 1 -C 6 alkenyl group, a C 3 -C 6 cycloalkyl group optionally substituted by a C 1 -C 3 alkyl group, or a benzyl group; or any two of T 4 , T 5 and T 6 may, together with the nitrogen atom to which they are bonded, form a 5-, 6-, 7- or 8-membered cyclic group optionally containing oxygen, nitrogen and/or sulfur atoms;
  • X and Z are independently substituents as freely selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a C 2 -C 5 alkenylsulfenyl group, a C 2 -C 5 alkenylsulfinyl group, a C 2 -C 5 alkenylsulfonyl group, a C 1 -C 4 haloalkylsulfenyl group, a C 1 -C 4 haloalkylsulfinyl group, a C 1 -C 4 haloalkyl
  • T 7 and T 8 each independently represent H, or a phenyl, benzyl or C 1 -C 6 alkyl group, or T 7 and T 8 may, together with the carbon atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring;
  • U 1 and U 2 each independently represent H, a C 1 -C 6 alkyl, C 2 -C, alkylcarbonyl, phenyl or benzyl group, or U 1 and U 2 may, together with the nitrogen atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring.
  • Q is a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R, (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl, pyrazolinyl, imidazol
  • A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl or imidazoliny
  • B is H, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkoxyalkyl group, CH 3 OC 2 H 4 OCH 2 , a C 1 -C 4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, —SO 2 CF 3 , a C 1 -C 8 dialkylaminosulfonyl group, a C 2 -C 9 dialkylaminothiocarbonyl group, a C 3 -C 9 alkoxycarbonylalkyl group, —C( ⁇ O)T 1 , —P( ⁇ O)T 2 T 8 , —P( ⁇ S)T 2 T 3 , an alkali metal atom, an alkaline earth metal atom, or NHT 4 T 5 T 6 ; and
  • T 1 is a C 1 -C 2 O alkyl group, a C 2 -C 6 alkenyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy-C 1 -C 4 alkyl group, a C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 3 -C 6 halocycloalkyl group, a C 3 -C 6 cycloalkyl group optionally substituted by a C 1 -C 3 alkyl group, a cycloalkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a cyclopropyl group substituted by both a phenyl optionally substituted by a halogen or a C 1 -C 4 alkyl group, and
  • Q is a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R, said heterocyclic group being
  • A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, said heterocyclic group being
  • A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-
  • A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, A-57, A-
  • A is a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-60, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70,
  • A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51,
  • A is a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-57, A-58, A-59,
  • A is a heterocyclic group optionally substituted by Y, said heterocyclic group being any of A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-
  • A is a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-1, A-2, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, A-57, A-58, A-59, A-60, A
  • R 1 is selected from a halogen atom, a C 1 -C 10 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a C 2 -C 6 alkenyloxy group, NO 2 , CN, —NU 1 U 2 , OH, a C 2 -C 7 alkoxycarbonyl group, a C 2 -C 4 alkoxyalkyl group, a C 2 -C 4 alkylcarbonyl group, a phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, a thienyl group optionally substituted by X, and —N ⁇ CT 7 T 8 (in which T 7 and T 8 each independently represent H, a phenyl, benzyl or C,-C, alky
  • Y 1 is selected from a halogen atom, a C 1 -C 10 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a C 2 -C 6 alkenyloxy group, NO 2 , CN, —NU 1 U 2 , OH, a C 2 -C 7 alkoxycarbonyl group, a C 2 -C 4 alkoxyalkyl group, a phenyl group optionally substituted by X, and —N ⁇ CT 7 T 8 (in which T 7 and T 8 each independently represent H, or a phenyl, benzyl or C 1 -C 6 alkyl group, or T 7 and T 8 may, together with the carbon atom to which they are bonded), form a 5-, 6-, 7- or 8-membered ring); or may, togeher with the adjacent Y 1 , form a 5-, 6- 7- or 8-membered ring an alky
  • X is a substituent of which the number is from 1 to 4 and which is freely selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a C 2 -C 5 alkenylsulfenyl group, a C 2 -C 5 alkenylsulfinyl group, a C 2 -C 5 alkenylsulfonyl group, a C 1 -C 4 haloalkylsulfenyl group, a C 1 -C 4 haloalkylsulfinyl group, a C 1
  • Z is a substituent of which the number is from 1 to 4 and which is freely selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a C 1 -C 4 alkenylsulfenyl group, a C 1 -C 4 alkenylsulfinyl group, a C 1 -C 4 alkenylsulfonyl group, NO 2 , CN, —NU 1 U 2 , a phenyl group, a phenoxy group, and a C 2 -C 5 alkoxycarbonyl group, (provided
  • n indicates the number of the substituents, and is 0, 1, 2 or 3;
  • n indicates the number of the substituents, and is 0, 1, 2, 3, or 4;
  • p indicates the number of substituents, and is 0, 1 or 2;
  • q indicates the number of the substituents, and is 0 or 1;
  • E is a heterocyclic group optionally substituted by a C 1 -C 4 alkyl or C 1 -C 4 haloalkyl group—(said heterocyclic group being a 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl or 1,3,4-oxadiazol-2-yl group)—or is a halogen atom, a C 2 -C 4 alkynyl group, a phenylethynyl group optionally substituted by Z, a C 1 -C 4 haloalkyl group, CN, NO 2 , N 3 , CHO, a C 2 -C 5 alkylcarbonyl group, a C 2 -C 5 alkoxycarbonyl group, a C 2 -
  • E is a heterocyclic group optionally substituted by a C 1 -C 4 alkyl or C 1 -C 4 haloalkyl group—(said heterocyclic group being a 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl or 1,3,4-oxadiazol-2-yl group)—or is a halogen atom, a C 2 -C 4 alkynyl group, a phenylethynyl group optionally substituted by a Z, a C 1 -C 4 haloalkyl group, CN, NO 2 , N 3 , CHO, a C 2 -C 5 alkylcarbonyl group, a C 2 -C 5 alkoxycarbonyl group, a C 2
  • Q is a phenyl group optionally subsitited by G, a naphthyl group, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-44, Q-45, Q-46, Q-49,
  • Y 2 is a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 akoxy group, NO 2 , CN, or a C 2 -C 5 alkoxycarbonyl group;
  • Y 3 is a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 4 alkoxyalkyl group, or a phenyl group optionally substituted by X.
  • the moiety —C(E) ⁇ C(OB)— of the compounds (I) of the present invention includes two isomers of E-form and Z-form, both of which are within the scope of the invention.
  • the heterocyclic group for Q, A and B indicates the following meanings.
  • thienyl is thiophen-2-yl or thiophen-3-yl
  • furyl is furan-2-yl or furan-3-yl
  • pyrrolyl is pyrrol-1-yl, pyrrrol-2-yl or pyrrol-3-yl
  • oxazolyl is oxazol-2-yl, oxazol-3-yl, oxazol-4-yl or oxazol-5-yl
  • thiazolyl is thiazol-2-yl, thiazol-4-yl or thiazol-5-yl
  • imidazolyl is imidazol-1-yl, imidazol-2-yl or imidazol-4-yl
  • isoxazolyl is isoxazol-3-yl, isoxazol-4-yl or isoxazol-5-yl
  • isothiazolyl is isothiazol-3-yl, isothiazol-4-y
  • QI phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl.
  • QII phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, , 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl.
  • AI phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl.
  • AII phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,3-thiadiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl.
  • AIII phenyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidinyl.
  • AIV thiazolyl, pyrazolyl, pyridinyl.
  • AVI pyrazolyl
  • AVII pyridinyl
  • Preferred scope of B is the following groups.
  • BI H, C 2 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, CH 3 OC 2 H 4 OCH 2 , C 1 -C 4 alkylsulfonyl, phenylsulfonyl optionally substituted by halogen or C 1 -C 4 alkyl, —SO 2 CF 3 , C 2 -C 8 dialkylaminosulfonyl, C 3 -C 9 dialkylaminothiocarbonyl, C 3 -C 9 alkoxycarbonylalkyl, —C( ⁇ O)T 1 , —P( ⁇ O)T 2 T 3 , —P( ⁇ S)T 2 T 3 , alkali metal, alkaline earth metal or NHT 4 T 5 T 6 .
  • BII H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, CH 3 OC 2 H 4 OCH 2 , C 1 -C 4 alkylsulfonyl, —SO 2 CF 3 , —C( ⁇ O)T 1 , alkali metal, alkaline earth metal or NHT 4 T 5 T 6 .
  • BIII H, C 2 -C 4 alkoxyalkyl, C 1 -C 4 alkylsulfonyl, —SO 2 CF 3 , —C( ⁇ O)T 1 , alkali metal, alkaline earth metal, NHT 4 T 5 T 6 .
  • BIV C 2 -C 4 alkoxyalkyl, C 1 -C 4 alkylsulfonyl, —SO 2 CF 3 , —C( ⁇ O)T 1 , alkali metal, alkaline earth metal or NHT 4 T 5 T 6 .
  • Preferred scope of E is the following grouips.
  • EI halogen, C 2 -C 4 alkynyl, phenylethynyl optionally substituted by Z, C 1 -C 4 haloalkyl, CN, NO 2 , N 3 , CHO, C 2 -C 5 alkylcarbonyl, C 2 -C 5 alkoxycarbonyl, C 2 -C 4 alkylaminocarbonyl, C 3 -C 9 dialkylaminocarbonyl, benzoyl optionally substituted by Z, aminothiocarbonyl, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, phenylsulfenyl optionally substituted by Z, phenylsulfinyl optionally substituted by Z, phenylsulfonyl optionally substituted by Z, —P( ⁇ O)T 2 T 3 , —P( ⁇ S)
  • EII halogen, C 2 -C 4 alkynyl, phenylethynyl optionally substituted by Z, CN, C 2 -C 5 alkylcarbonyl, C 2 -C 5 alkoxycarbonyl, C 2 -C 4 alkylaminocarbonyl, C 3 -C 9 dialkylaminocarbonyl, benzoyl optionally substituted by Z, aminothiocarbonyl, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, phenylsulfenyl optionally substituted by Z, phenylsulfinyl optionally substituted by Z, phenylsulfonyl optionally substituted by Z or —P( ⁇ O)T 2 T 3 .
  • GI substituents freely selected from halogen, C 1 -C 6 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 3 -C 6 cycloalkyl optionally substituted by C 1 -C 3 alkyl, C 1 -C 6 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 2 -C 4 haloalkenyloxy, C 3 -C 4 haloalkynyloxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenylsulf
  • GII substituents freely selected from halogen, C 1 -C 6 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 1 -C 6 cycloalkyl optionally substituted by C 1 -C 3 alkyl, C 1 -C 6 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 2 -C 4 haloalkenyloxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4
  • GIII substituents freely selected from halogen C 1 -C 6 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl optionally substituted by C 1 -C 3 alkyl, C 1 -C 6 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 2 -C 4 haloalkenyloxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsufonyl, C 2 -C 4 alkynylsulfenyl, C 2 -C 4 alkynylsul
  • RI substituents freely selected from halogen, C 1 -C 6 alkyl, C 1 -C 3 alkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl optionally substituted by C 1 -C 3 alkyl, C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 haloalkynyloxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulf
  • RII substituents freely selected from halogen, C 1 -C 6 alkyl, C 1 -C 3 alkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl optionally substituted by C 1 -C 3 alkyl, NO 2 , CN, —NU 1 U 2 , naphthyl, C 2 -C 4 alkoxycarbonyl, C 1 -C 4 alkoxyalkyl, phenyl optionally substituted by X, and pyridyl optionally substituted by X (provided that when the substituents is two or more, said substituents may be the same or different), and the number of the substituents, R, is 1, 2 or 3.
  • RIII substituents freely selected from halogen, C 1 -C 6 alkyl, C 1 -C 3 alkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl optionally substituted by C 1 -C 3 alkyl, NO 2 , CN, —NU 1 U 2 , naphthyl, C 2 -C 4 alkoxycarbonyl, phenyl optionally substituted by X, and pyridyl optionally substituted by X (provided that when the substituent is two or more, said substituents may be the same or different), and the number of the substituent R, is 1 or 2.
  • the number of R differs.
  • the number of R is 0 or 1, preferably 1.
  • the number of R is an integer of from 0 to 2, preferably 1 or 2.
  • the number of R is an integer of from 0 to 3, preferably an integer of from 0 to 2, member preferably 1 or 2.
  • the number of R is an integer of from 0 to 4, preferably an integer of from 0 to 3, more preferably 1 or 2.
  • Preferred scope of Y is the following groups.
  • YI substituents freely selected from halogen, C 1 -C 6 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 haloalkynyloxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 alkynylsulfenyl, C 2 -C 4 alkynylsulfenyl, C 2 -
  • YII substituents freely selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, NO 2 ,CN, C 2 -C 4 alkoxycarbonyl, and phenyl optionally substituted by X (provided that when the substituent is two or more, said substituents may be the same or different) and the number of the substituent, Y, is 1, 2 or 3.
  • the number of Y differs.
  • the number of Y is 0 or 1, preferably 1.
  • the number of Y is an integer of from 0 to 2, preferably 1 or 2.
  • the number of Y is an integer of from 0 to 3, preferably an integer of from 0 to 2, more preferably 1 or 2.
  • the number of Y is an integer of from 0 to 4, preferably an integer of from 0 to 3, more preferably 1 or 2.
  • WI substituents freely selected from halogen, C 1 -C 6 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 haloalkenyls
  • WII substituents freely selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulfinyl, C 1 -C 4 alkenylsulfony, C 2 -C 4 alkynyloxy, C
  • WIII substituents freely selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, NO 2 , and CN (provided that when the substituent is two or more, the substituents may be the same or different) and the number of the substituent, W, is 1 or 2.
  • T 1 Preferred scope of T 1 is the following groups.
  • T 1 I C 1 -C 18 alkyl, C 2 -C 6 alkenyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkyl optionally substituted by C 1 -C 3 alkyl, cycloalkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 2 -C 4 alkenyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 1 -C 10 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 6 alkenyloxy, C 3 -C 6 cycloalkoxy optionally substituted by
  • heterocyclic group being selected from thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, and 1,2,4-triazinyl groups).
  • T 1 II C 1 -C 1 alkyl, C 2 -C 6 alkenyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, C 1 -C 4 alkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl optionally substituted by C 1 -C 3 alkyl, cycloalkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 2 -C 4 alkenyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 1 -C 10 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 5 alkenyloxy, C 3 -C 6 cycloalkoxy, benzyloxy, C 2 -C 5 alkoxycarbonyl, phenyl optionally substitute
  • T 1 III C 1 -C 17 alkyl, C 2 -C 6 alkenyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxyalkyl, C 1 -C 4 alkyl substituted by phenyl, C 3 -C 6 cycloalkyl optionally substituted C 1 -C 3 alkyl, cycloalkyl substituted by phenyl, C 2 -C 4 alkenyl substituted by phenyl, C 1 -C 8 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 5 alkenyloxy, C 3 -C 6 cycloalkoxy, benzyloxy, C 1 -C 5 alkoxycarbonyl, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, phenylthio, naphthyl, pyrazolyl optionally substituted by Z or pyridinyl optionally substituted by Z.
  • T 2 Preferred scope of T 2 is the following groups.
  • T 2 I phenyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy of C 1 -C 4 alkylsulfenyl.
  • T 4 Preferred scope of T 4 is the following groups.
  • T 3 I phenyl, C 1 -C 4 alkyl, C 3 -C 6 alkoxy or C 1 -C 4 alkylsulfenyl.
  • T 4 Preferred scope of T 4 is the following groups.
  • T 4 I H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or benzyl. Also preferred is such that any two of T 4 , T 5 and T 6 , together with the nitrogen atom to which they are bonded, forms a 5-, 6- or 7-membered ring optionally having oxygen, nitrogen and/or sulfur atoms.
  • T 5 Preferred scope of T 5 is the following groups.
  • T 5 I H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or benzyl. Also, preferred is such that any two of T 4 , T 5 and T 6 , together with the nitrogen atom to which they are bonded, forms a 5-, 6- or 7-membered ring optionally having oxygen, nitrogen and/or sulfur atoms.
  • T 6 I H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or benzyl. Also, preferred is such that any two of T 4 , T 5 and T 6 , together with the nitrogen atom to which they are bonded, forms a 5-, 6- or 7-membered ring optionally having oxygen, nitrogen and/or sulfur atoms.
  • XI substituents freely selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 5 alkenylsulfenyl, C 2 -C 5 alkenylsulfinyl, C 2 -C 5 alkenylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, NO 2 , CN, —NU 1 U 2 and C 2 -C 5 alkoxycarbonyl (provided that the substituent is two or more, said
  • XII substituents freely selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 5 alkenylsulfenyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, and NO 2 (provided that when the substituent is two or more, said substituents may be the same or (different) and the number of the substituent X, is 1, 2 or 3.
  • XIII substituents freely selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, and C 1 -C 4 alkoxy (provided that when the substituent is two is more, said substituents may be the same or different) and the number of the substituent, X, is 1 or 2.
  • the number of X differs.
  • the number of X is an integer of from 0 to 5, preferably an integer of from 0 to 3, more preferably an integer of from 0 to 2.
  • the number of X is an integer of from 0 to 4, preferably 0, 1 or 2, more preferably 0 or 1.
  • the number of X is an integer of from 0 to 3, preferably 0 or 1.
  • ZI substituents freely selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1-C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 5 alkenylsulfenyl, C 2 -C 6 alkenylsulfinyl, C 2 -C, alkenylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, NO 2 , CN, —NU 1 U 2 and C 2 -C 5 alkoxycarbonyl (provided that when the substituent is two or more, said substituent
  • ZII substituents freely selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 5 alkenylsulfenyl, C 2 -C 5 alkenylsulfinyl, C 2 -C 5 alkenylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl and C 1 -C 4 haloalkylsulfonyl (provided that when the substitutent is two or more, said substituents may be the same or different) and the substituent Z, is 1, 2, 3, or 4.
  • the number of Z differs.
  • the number of Z is an integer of from 0 to 5, preferably an integer of from 0 to 4, more preferably 0, 1, 2 or 3, even more preferably 0, 1 or 2.
  • the number of Z is an integer of from 0 to 7, preferably 0.
  • the number of the substituents of Z also differs depending on the type of the heterocyclic group.
  • the number of Z is 0 or 1.
  • the number of Z is an integer of from 0 to 2, preferably 1 or 2.
  • the number of Z is an integer of from 0 to 3, preferably an integer of from 0 to 2, more preferably 1 or 2.
  • the number of Z is an integer of from 0 to 4, preferably an integer of from 0 to 2, more preferably 1 or 2.
  • T 7 Preferred scope of T 7 is the following groups.
  • T 7 I H, phenyl, benyzl or C 1 -C 4 alkyl. Also preferred is such that T 7 and T 8 , together with the carbon atom to which they are bonded, form a 5-membered or 6-membered ring.
  • T 8 Preferred scope of T 8 is the following groups.
  • T 8 I phenyl, benzyl or C 1 -C 4 alkyl. Also preferred is such that T 7 and T 8 , together with the carbon atom to which they are bonded, form a 5-membered or 6 -membered ring.
  • U 1 I H, C 1 -C 4 alkyl or C 2 -C 5 alkylcarbonyl. Also preferred is such that U 1 and U 2 , together with nitrogen atom to which they are bonded, form a 5-, 6- or 7-membered ring.
  • U 2 I H, C 1 -C 4 alkyl or C 2 -C 5 alkylcarbonyl. Also preferred is such that U 1 and U 2 , together with the carbon atom to which they are bonded, form a 5-, 6- or 7-membered ring.
  • m is 1, 2, or 3, more preferably 1 or 2.
  • n 0, 1, 2 or 3, more preferably 1 or 2.
  • p is 1 or 2.
  • the halogen atom for E, G, R, R 1 , W, X, Y, Y 1 , Y 2 , Y 3 and Z includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Preferred are a fluorine atom, a chlorine atom and a bromine atom.
  • the alkyl group for B, G, R, R 1 , T 1 , T 2 , T 3 , T 4 , T 5 , T 6 , T 7 , T 8 , U 1 , U 2 , W, X, Y, Y 1 , Y 2 , Y 3 and Z may be a straight chain or branched alkyl group having indicated carbon atoms, which includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, pentyl-1, pentyl-2, pentyl-3, 2-methylbutyl-1, 2-methylbutyl-2, 2-methylbutyl-3, 3-methylbutyl-1, 2,2-dimethylpropyl-1, hexyl-1, hexyl-2, hexyl-3, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-
  • the alkenyl group for G, R, R 1 , T 1 , T 4 , T 5 , T 6 , Y 1 and W may be a straight chain or branched alkenyl group having indicated carbon atoms, which includes, for example, ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl
  • the alkynyl group for E, G, R, R 1 , Y 1 and W may be a straight chain or branched alkynyl group having indicated carbon atoms, which includes, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, hexynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl ,1a-dimethyl-2-butyny
  • the haloalkyl group for B, E, G, R, R 1 , T 1 , W, X, Y, Y 1 , Y 2 , Y 3 and Z may be a straight chain or branched haloalkyl group having indicated carbon atoms, which includes, for example, fluoromethyl, chloromethyl, bromomethyl, fluoroethyl, chloroethyl, bromoethyl, fluoro-n-propyl, chloro-n-propyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethl, difluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluoroethyl, hexafluoro-n-propyl, chlorobutyl, fluorobutyl, chloro-n-
  • the C 3 -C 6 cycloalkyl group optionally substituted by a C 1 -C 3 alkyl group for G, R, T 1 , T 4 , T 5 and T 6 includes, for example, cyclopropyl, 1-methylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, 1-ethylcyclobutyl, 1-n-butylcyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 1-methylcyclohexyl and 4-methylcyclohexyl groups.
  • the C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group for B, G, R and T 1 includes, for example, benzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-tert-butylbenzyl, 1-phenylethyl, 1-(3-chlorophenyl)ethyl, 2-phenylethyl, 1-methyl-1-phenylethyl, 1-(4-chlorophenyl)-1-methylethyl, 1-(3-chlorophenyl)-1-methylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 1-phenylpropyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl, 1-methyl-1-phenylpropyl,
  • the C 3 -C 6 cycloalkyl group substituted by a phenyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group includes, for example, 1-phenylcyclopropyl, 1-(3-chlorophenyl)cyclopropyl, 1-(4-chlorophenyl)cyclopropyl, 1-(4-bromophenyl)cyclopropyl, 1-(4-fluorophenyl)cyclopropyl, 1-(4-ethylphenyl) cyclopropyl, 1-(4-propylphenyl)cyclopropyl, 2-phenylcyclopropyl, 1-phenylcyclobutyl, 2-phenylcyclobutyl, 1-phenylcyclopentyl, 1-(4-chlorophenyl)cycloptentyl, 2-phenylcyclopentyl, 3-phenylcyclopentyl, 1-phenylcyclopropyl
  • the cyclopropyl group substituted by both a phenyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group and a C 1 -C 4 alkyl group includes, for example, 2,2-dimethyl-1-phenylcyclopropyl, 1-(4-chlorophenyl)-2,2-dimethylcyclopropyl, 2,2-dimethyl-3-phenylcyclopropyl, 3-(3-chrlorophenyl)-2,2-dimethylcyclopropyl, (4-chlorophenyl)-2,2-dimethyl-3-phenylcyclopropyl, (4-bromophenyl)-2,2-dimethyl-3-phenylcyclopropyl, 2,2-dimethyl-3-(4-methylphenyl) cyclopropyl and (4-tert-butylphenyl)-2,2-dimethyl-3-phenylcyclopropyl groups.
  • the C 3 -C 4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen atom or a C 1 -C 4 alkoxy group and a halogen atom includes, for example, 2,2-dichloro-1-phenylcyclopropyl, 2,2-dichloro-1-(3-chlorophenyl)cyclopropyl, 2,2-dichloro-1-(4-methoxyphenyl)cyclopropyl, 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropyl, 2,2-dichloro-(4-i-propyloxyphenyl)cyclopropyl, 2,2-dichloro-(4-t-butylphenyl)cyclopropyl, 2,2-dichloro-1-(4-methoxyphenyl)-3-phenylcyclopropyl and 1-(4-ethoxyphenyl)-2,2,3,3-t
  • the cyclopropyl group substituted by both a C 2 -C 4 alkenyl group optionally substituted by a halogen atom, and a C 1 -C 4 alkyl group includes, for example, 2,2-dimethyl-3-(2,2-dimethylethenyl)cyclopropyl, 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropyl, 3-(2,2-dichloroethyenyl)-2,2-dimethylcyclopropyl and 3-(2,2-chlorotrifluoroethenyl)-2,2-dimethylcyclopropyl groups.
  • the C 3 -C 6 cycloalkoxy group optionally substituted by a C 1 -C 3 alkyl group includes, for example, cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy and 1-methylcyclopropoxy groups.
  • the C 2 -C 4 alkenyl group substituted by a phenyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group includes, for example, 1-phenylethenyl, 2-phenylethenyl, 2-(2-chlorophenyl)ethenyl, 2-(3-chlorophenyl)ethenyl, 2-(4-chlorophenyl)ethenyl, 2-(4-methylphenyl)ethenyl, 2-(2,6-difluorophenyl)ethenyl, 2-(2,5-dimethylphenyl)ethenyl, 1-methyl-2-phenylethenyl, 2-phenyl-1-propenyl, 2-(4-bromophenyl)-1-propenyl and 2-(2,4,6-trimethylphenyl)-1-propenyl groups.
  • the alkoxy group for G, R, T 1 , T 2 , T 3 , R 1 , W, X, Y, Y 1 , Y 2 and Z may be straight chain or branched alkoxy group having indicated carbon atoms, which includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-di
  • the C 3 -C 6 halocycloalkyl group for G, R and T 1 includes, for example, fluorocyclopropyl, difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, chlorocyclobutyl, dichlorocyclobutyl, chlorocyclopentyl, dichlorocyclopentyl, chlorocyclohexyl, dichlorocyclohexyl and tetrafluorocyclobutyl groups.
  • the group —NU 1 U 2 for G, R, R 1 , T 1 , W, X, Y, Y 1 and Z includes, for example, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, tert-butylamino, n-pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, n-hexylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino,
  • the C 2 -C 5 alkoxycarbonyl group for E, G, R, R 1 T 1 , W, X, Y, Y 1 , Y 2 and Z includes, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, iso-butoxycarbonyl and tart-butoxycarbonyl groups.
  • the C 1 -C 4 haloalkoxy group for G, R, T 1 , W, X, Y and Z may be a straight chain or branched C 1 -C 4 haloalkoxy group, including, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, fluorcethoxy, chlorcethoxy, bromcethoxy, difluoroethozy, trifluoroethoxy, tetrafluoroethoxy, pentafluorcethoxy, trichloroethoxy, trifluorochlorethoxy, fluoropropoxy, chloropropoxy, bromopropoxy, fluorobutoxy, chlorobutoxy, fluoro-iso-propoxy and chloro-iso-propoxy groups.
  • the C 1 -C 4 alkylsulfenyl group for E, G, R, T 2 , T 3 , W, X, Y and Z includes, for example, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec-butylthio and tert-butylthio groups.
  • the C 1 -C 4 alkylsulfinyl group for E, G, R, X, W, Y and Z includes, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl, iso-butylsulfinyl, sec-butylsulfinyl and tart-butylsulfinyl groups.
  • the C 1 -C 4 alkylsulfonyl group for B, E, G, R, W, X, Y and Z includes, for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl, n-butylsulfonyl, iso-butylsulfonyl, sec-butylsulfonyl and tart-butylsulfonyl groups.
  • the C 2 -C 4 alkoxyalkyl group for B, G, R, R 1 , T 1 , Y, Y 1 and Y 2 includes, for example, C 1 -C 3 alkoxy-methyl, C 1 -C 2 alkoxy-ethyl, methoxyethoxymethyl and methoxypropyl groups.
  • the C 2 -C 4 alkylcarbonyl group for E, G, R, R 1 , U 1 , U 2 , Y 1 , Y 2 and W includes, for example, acetyl, propionyl, butanoyl and iso-butanoyl groups.
  • the C 2 -C 6 haloalkylcarbonyl group for G and W includes, for example, chloroacetyl, trifluoroacetyl, 3,3,3-trifluoropropionyl and pentafluoropropionyl groups.
  • the C 2 -C 5 haloalkylcarbonyloxy group for G, R and Y includes, for example, chloroacetyloxy, trifluoroacetyloxy, 3,3,3-trifluoropropionyloxy and pentafluoropropionyloxy groups.
  • the C 3 -C 7 dialkylaminocarbonyloxy group for G and Y includes, for example, dimethylaminocarbonyloxy, diethylaminocarbonyloxy and di-i-propylaminocarbonyloxy groups.
  • the naphthyl group for R, Y, Z and T 1 includes, for example, 1-naphthyl and 2-naphthyl groups.
  • the pyridyl group optionally substituted by Z for G and T 1 includes, for example, 2-pyridyl, 3-pyridyl and 4-pyridyl groups all optionally substituted by Z.
  • Preferred are 2-pyridyl and 3-pyridyl groups both optionally substituted by Z; and more preferred is a 2-pyridyl group optionally substituted by Z.
  • the pyridyloxy group optionally substituted by Z for G and T 1 includes, for example, 2-pyridyloxy, 3-pyridyloxy and 4-pyridyloxy groups all optionally substituted by Z.
  • the pyridyl group optionally substituted by X for R and R 1 includes, for example, 2-pyridyl, 3-pyridyl and 4-pyridyl groups all optionally substituted by X.
  • Preferred are 2-pyridyl and 3-pyridyl groups both optionally substituted by X; and more preferred is a 2-pyridyl group optionally substituted by X.
  • the pyridyloxy group optionally substituted by X for N and R 1 includes, for example, 2-pyridyloxy, 3-pyridyloxy and 4-pyridyloxy groups all optionally substituted by X.
  • the thienyl group-optionally substituted by X for R and R 1 includes, for example, 2-thienyl and 3-thienyl groups both optionally substituted by X.
  • the thienyl group optionally substituted by Z for G and Y 1 includes, for example, 2-thienyl and 3-thienyl groups both optionally substituted by Z.
  • the group —N ⁇ CT 7 T 8 for G, R, R 1 , Y and Y 1 indicates an alkylidenamino group, a benzylidenamino group, an arylidenamino group or a cycloalkylidenamino group, including, for example, methylidenamino, ethylidenamino, propylidenamino, isopropylidenamino, 4-methyl-2-pentylidenamino, cyclopentylidenamino and cyclohexylidenamino groups.
  • the C 2 -C 4 alkylaminocarbonyl group for E includes, for example, methylaminocarbonyl, ethylaminocarbonyl and n-propylaminocarbonyl groups.
  • the C 3 -C 9 dialkylaminocarbonyl group for E includes, for example, dimethylaminocarbonyl, diethylaminocarbonyl, di-n-propylaminocarbonyl, di-isopropylaminocarbonyl and di-n-butylaminocarbonyl groups.
  • the C 1 -C 4 alkylaminosulfonyl group for B includes, for example, methylaminosulfonyl, ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl and n-butylaminosulfonyl groups.
  • the C 2 -C 8 dialkylaminosulfonyl group for B includes, for example, dimethylaminosulfonyl, diethylaminosulfonyl, di-n-propylaminosulfonyl, di-isopropylaminosulfonyl and di-n-butylaminosulfonyl groups.
  • the C 2 -C 5 alkylaminothiocarbonyl group for B includes, for example, methylaminothiocarbonyl, ethylaminothiocarbonyl, n-propylaminothiocarbonyl, isopropylaminothiocarbonyl and n-butylaminothiocarbonyl groups.
  • the C 3 -C 9 dialkylaminothiocarbonyl group for B includes, for example, dimethylaminothiocarbonyl, diethylaminothiocarbonyl, di-n-propylaminothiocarbonyl, di-isopropylaminothiocarbonyl and di-n-butylaminothiocarbonyl groups.
  • the C 1 -C 4 alkyl group substituted by a benzoyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group for B includes, for example, phenacyl, 2-fluorophenacyl, 3-chlorophenacyl, 4-bromophenacyl, 2-methylphenacyl,3-ethylphenacyl,4-i-propylphenacyl and 4-t-butylphenacyl groups.
  • the phenylsulfonyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group for B includes, for example, 2-fluorophenylsulfonyl, 4-fluorophenylsulfonyl, 2-chlorophenylsulfonyl, 4-chlorophenylsulfonyl, 4-bromophenylsulfonyl, 2,5-dichlorophenylsulfonyl, pentafluorophenylsulfonyl, 4-methylphenylsulfonyl, 2-methylphenylsulfonyl, 4-t-butylphenylsulfonyl, 2,5-dimethylphcnylsulfonyl, 2,4-dimethylphenylsulfonyl, 2,4,6-trimethylphenylsulfonyl and 2,4,6-tri-i-propylphenylsul
  • the C 2 -C 5 cyanoalkyl group for G and B includes, for example, cyanomethyl, 2-cyanoethyl, 3-cyanopropyl and 1-cyano-1-methylethyl groups.
  • the C 3 -C 9 alkoxycarbonylalkyl group for B may be a straight chain or branched one, including, for example, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycerbonylmethyl, i-propoxycarbonylmethyl, n-butoxycarbonylmethyl, i-butoxycarbonylmethyl, t-butoxycarbonylmethyl, n-hexyloxycarbonylmethyl, n-heptyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-n-butoxyethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 1-methoxycarbonylpropyl, 3-ethoxycarbonylpropyl, 4-methoxycarbonylbutyl, 6-ethoxycarbonylhexyl, 1-methoxycarbonyl-1-methylethyl, 1-iso-propoxycarbonyl-1
  • the alkali metal for B includes, for example, lithium sodium and potassium.
  • the alkaline earth metal for H includes, for example, magnesium, calcium, strontium and barium. Preferred are magnesium, calcium and barium.
  • the ammonium group of NHT 4 T 5 T 6 for B includes, for example, ammonium, monomethylammonium, dimethylammonium, trimethylammonium, diethylammonium, triethylammonium, di-isopropylammonium, di-isopropylethylammonium, hexylmethylammonium, cyclopropylmethylammonium, cyclohexylmethylammonium, allylmethylammonium, benzylmethylammonium and 4-methylcyclohexylethylammonium groups.
  • T 4 , T 5 and T 6 may form, along with the nitrogen atom to which they are bonded, a heterocyclic, 5-, 6-, 7- or 8-membered ammonium group optionally having oxygen, nitrogen and/or sulfur atoms.
  • the methoxy group substituted by a phenyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group for G includes, for example, benzyloxy, 2-chlorobenzyloxy, 3-chlorobenzyloxy, 4-chlorobenzyloxy, 3-methylbenzyloxy, 4-t-butylbenzyloxy, 2,6-difluorobenzyloxy and 2-fluoro-4-chlorobenzyloxy groups.
  • the heterocyclic, 5-, 6-, 7- or 8-membered ammonium group optionally having oxygen, nitrogen and/or sulfur atoms, which is formed by two of T 4 , T 5 and T 6 along with the nitrogen atom to which they are bonded includes, for example, pyrrolidine, pyrazolidine, imidazolidine, oxazolidine, isoxazolidine, thiazolidine, piperazine, piperazine, morpholine, thiamorpholine, hexamethylenimine and heptamethylenimine groups.
  • the haloalkylsulfenyl group for G, R, W, X, Y and Z may be a straight chain or branched C 1 -C 4 haloalkylthio group, including, for example, fluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, fluoroethylthio, pentafluoroethylthio and fluoro-iso-propylthio groups.
  • the haloalkylsulfinyl group for G, R, W, X, Y and Z may be a straight chain or branched, C 1 -C 4 haloalkylsulfinyl group, including, for example, fluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, fluorcethylsulfinyl, pentafluoroethylsulfinyl and fluoro-iso-propylsulfinyl groups.
  • the haloalkylsulfonyl group for G, R, W, X, Y and Z may be a straight chain or branched, C 2 -C 4 haloalkylsulfonyl group, including, for example, fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, ftuoroethylsulfonyl, pentafluoroethylsulfonyl and fluoro-isopropylsulfonyl groups.
  • the heloalkenyl group for G, R, T 1 and W may be a straight chain or branched C2-C 4 haloalkenyl group, including, for example, 2-chloroethenyl, 2-bromoethenyl-and 2,2-dichloroethenyl groups.
  • the alkenyloxy group for G, R, R 1 , T 1 , W, Y and Y 1 may be a straight chain or branched C 2 -C 4 alkenyloxy group, including, for example, allyloxy, 2-propenyloxy, 2-butenyloxy and 2-methyl-2-propenyloxy groups.
  • the haloalkenyloxy group for G, R, W and Y may be a straight chain or branched C 2 -C 5 haloalkenyloxy group, including, for example, 3-chloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 4-chloro-2-butenyloxy, 4,4-dichloro-3-butenyloxy and 4,4-difluoro-3-butenyloxy groups.
  • the alkenylsulfenyl group for G, R, W, X, Y and Z may be a straight chain or branched C 2 -C 4 alkenylsulfenyl group, including, for example, allylsulfenyl, 2-propenylsulfenyl, 2-butenylsulfenyl and 2-methyl-2-propenylsulfenyl groups.
  • the alkenylsulfinyl group for G, R, W, X, Y and Z may be a straight chain or branched C 2 -C 5 alkenylsulfinyl group, including, for example, allylsulfinyl, 2-propenylsulfinyl, 2-butenylsulfinyl and 2-methyl-2-propenylsulfinyl groups.
  • the alkenylsulfonyl group for G, R, W, X, Y and Z may be a straight chain or branched C 2 -C 4 alkenylsulfonyl group, including, for example, allylsulfonyl, 2-propenylsulfonyl, 2-butenylsulfonyl and 2-methyl-2-propenylsulfonyl groups.
  • the haloalkenylsulfenyl group for G, R, W and Y may be a straight chain or branched C, C, haloalkenylsulfenyl group, including, for example, 3-chloro-2-propenylsulfenyl, 4-chloro-2-butenylsulfenyl, 3,3-dichloro-2-propenylsulfenyl, 4,4-dichloro-3-butenylsulfenyl and 4,4-difluoro-3-butenylsulfenyl groups.
  • the haloalkenylsulfinyl group for G, R, W and Y may be a straight chain or branched C 2 -C 4 haloalkenylsulfinyl group, including, for example, 3-chloro-2-propenylsulfinyl, 3,3-dichloro-2-propenylsulfinyl, 4-chloro-2-butenylsulfinyl, 4,4-dichloro-3-butenylsulfinyl and 4,4-difluoro-3-butenylsulfinyl groups.
  • the haloalkenylsulfonyl group for G, R, W and Y may be a straight chain or branched C 2 -C 4 haloalkenylsulfonyl group, including, for example, 3-chloro-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl, 4-chloro-2-butenylsulfonyl, 4,4-dichloro-3-butenylsulfonyl and 4,4-difluoro-3-butenylsulfonyl groups.
  • the C 2 -C 4 haloalkynyl group for G, R and W includes, for example, chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-1-propynyl and 3-bromo-1-butynyl groups.
  • the C 2 -C 4 alkenyloxy group for G, R, W and Y includes, for example, 2-propynyloxy, 2-butenyloxy and 1-methyl-2-propynyloxy groups.
  • the C 2 -C 4 haloalkenyloxy group for G, R, W and Y includes, for example, 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy and 3-iodo-2-propynyloxy groups.
  • the C 2 -C 6 alkenylsulfenyl group for G, R, W and Y includes, for example, 2-propynylsulfenyl, 2-butynylsulfenyl and 1-methyl-2-propynylsulfenyl groups.
  • the C 2 -C 6 alkenylsulfinyl group for G, R, W and Y includes, for example, 2-propynylsulfinyl, 2-butenylsulfinyl and 1-methyl-2-propynylsulfinyl groups.
  • the C 2 -C 6 alkenylsulfonyl group for G, R, W and Y includes, for example, 2-propynylsulfonyl, 2-butynylsulfonyl and 1-methyl-2-propynylsulfonyl groups.
  • the C 2 -C 6 haloalkenylsulfenyl group for G, R, W and Y includes, for example, 3-chloro-2-propynylsulfenyl, 3-bromo-2-propynylsulfenyl and 3-iodo-2-propynylsulfenyl groups.
  • the C 2 -C 6 haloalkenylsulfinyl group for G, R, W and Y includes, for example, 3-chloro-2-propynylsulfinyl, 3-bromo-2-propynylsulfinyl and 3-iodo-2-propynylsulfinyl groups.
  • the C 2 -C 6 haloalkynylsulfonyl group for G, R, W and Y includes, for example, 3-chloro-2-propynylsulfonyl, 3-bromo-2-propynylsulfonyl and 3-iodo-2-propynylsulfonyl groups.
  • the C 2 -C 4 alkylcarbonyloxy group for G, R, W and Y includes, for example, acetoxy, propanoyloxy, butanoyloxy and isopropylcarbonyloxy groups.
  • the benzoyl group optionally substituted by X for E and G includes, for example, benzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 4-bromobenzoyl, 4-fluorobenzoyl, 3-methylbenzoyl, 4-methylbenzoyl, 4-tert-butylbenzoyl and 3,4-dichlorobenzoyl groups.
  • the compounds of the present invention effectively prevent various pests, which include, for example, so-called agricultural insect pests that injure agricultural and horticultural crops and trees, so-called live-stock insect pests that live on livestock and poultry, so-called sanitary insect pests that have various negative influences on the human living environment including houses, so-called stored products insect pests that injure grains stored in storehouses, and also acarids, nematodes, molluscs and crustaceans that live in the same sites as above and injure those mentioned above.
  • insect pests stands, nematodes, molluscs and crustaceans capable of being exterminated by the compounds of the present invention are mentioned below, which, however, are not limitative.
  • Insect pests of Lepidoptera such as rice stem borer ( Chilo suppressalis Walker), rice leafroller ( Cnaphalocrocis medinalis Guenée), green rice caterpillar ( Naranga aenescens Moore), rice skipper ( Parnara guttata Bremer et Gvey), diamond back moths ( Plutella xylostella Linneé), cabbage armyworms ( Mamestra brassicae Linneé), common white ( Pieris rapae crucivora Boisduval), turnip moth ( Agrotis segetum Denis et Schiffermüller), common cutworn ( Spodptera litura Fabricius), beet armyworm ( Spodoptera exigua Hübner), smaller tea tortrix (Adoxophyes sp.), oriental tea tortrix ( Homona magnanima Diakonoff), peach fruit moth ( Carposina niponensis Walsingham), oriental fruit moth ( Grapholita molest
  • Insect pests of Hemiptera such as green rice leafhopper ( Nephotettix cincticeps Uhler), brown rice planthoppers ( Nilaparvata lugens Stal), green peach aphid ( Myzus persicae Sulzer), cotton aphid ( Aphis gossypii Glover), green-house whitefly ( Trialeurodes vaporariorum Westwood), sweetpotato white fly ( Bemisia tabaci Gennadius), pear psylla ( Psylla pyricola Forster), azalea lace bug ( Stephanitis pyrioides Scott), arrowhead scale ( Unaspis yanonensis Kuwana), comstock mealybug ( Pseudococcus comrtocki Kuwana), red wax scale ( Ceroplastes rubens Maskell), brown-mamrorated stinkbug (Halyomorpha mists Uhler), cabbage bug ( Eury
  • Insect pests of Coleoptera such as twenty-eight-spotted ladybird ( Henosepilachna vigintioctopunctata Fabricius), cupreous chafers ( Anomala cuprea Hope), ricewater weevil ( Lissorhoptrus oryzophilus Kuschel), sweetpotato weevil ( Cylas formicarius Fabricius), cucurbit leaf beetle ( Aulacophora femoralis Motschulsky), striped flea beetle (Phyllotreta striolata Fablicius), white-spotted longicom beetle ( Anoplophora malasiaca Thomson), pine sawyers ( Monochamus alternatus Hope), corn rootworms (Diabrotica spp.), rice weevil ( Sitophilus zeamais Motschulsky), lesser rice weevil ( Sitophilus oryzae Linneé), granary weevils ( Sitophilus granarius Linneé), red four bee
  • Insect pests of Diptera such as legume leafminer ( Liriomyza trifolii Burgess), seedcorn maggot ( Delis platura Meigen), Hessia fly ( Mayetiola destructor Say), melon fly (Dacus (Zengodacus) cucurbitae Coquillett), Mediterranear fruit fly ( Ceratitis capitata Wiedemann), house flies ( Musca domestics Linneé), stable fly ( Stomoxys calcitrans Linneé), Sheep ked ( Melophagus orinus ), common cattle grub ( Hypoderm lineatum devillers), nothern cattle grub ( Hypoderma baris Linneé), sheep botfly ( Oestrus ovis Linneé), tsetse fly ( Golossina palpalis Robineau-Desvoidy), common gnat ( Culex pipiens pollens Coquillett), yellow-fever mosquitoes ( Aedes aegyp
  • Insect pests of Hymenoptera such as cabbage sawfly ( Athalis rosae ruficornis Jakovlev), pine sawfly ( Neodiprion sertifer Geoffroy), chestnut sawfly ( Apethymus kuri Takeuchi), etc.;
  • Thysanoptera Insect pests of Thysanoptera, such as melon thrips ( Thrips palmi Karny), onion thrips ( Thrips tabaci Lindeman), western flower thrips ( Frankliniella occidentalis Pergande), flower thrip ( Frankliniella intonsa Trybom), yellow tea thrip ( Scirtothrips dorsalis Hood), etc.;
  • Insect pests of Dictyoptera such as smokybrown cockroache ( Periplaneta fuliginosa Serville), Japanese cockroach ( Periplaneta japonica Kamy), German cockroaches ( Blattella germanica Linneé), etc.;
  • Insect pests of Orthoptera such as oriental migratory locust ( Locusts migratoria Linneé), rice grasshopper ( Oxya yezoensis Shiraki), desert locust ( Schistocetca gregaria Forskal), etc.;
  • Insect pests of Isoptera such as Formosan subterranean tetmit ( Coptotermes formosanus Shiraki), ( Reticulitermes Leucotermes speratus Kolbe), ( Odontotermes formosanus Shirakif), etc.;
  • Insect pests of Siphonaptera such as cat fleas ( Ctenocephalides felis Bouché), human fleas ( Pulex irritans Linneé), oriental rat flea ( Xenopsylla cheopis Rothschild), etc.;
  • Insect pests of Mallophaga such as Chicken bodylouse ( Menacanthus stramineus Nitsch), cattle biting louse ( Bavicola bovis Linneé), etc.;
  • Insect pests of Anoplura such as short-nosed cattle louse ( Haematopinus eurysternus Nitzsh), hog louse ( Haematopinus suis Linneé), longnosed cattle louse ( Linognathus vituli Linneé), little cattle louse ( Solenopates capillatus Enderlein), etc.
  • Pests of TETRANYCHIDAE such as citrus red mite ( Panonychus cirri McGregor), European red mite ( Panonychus ulmi Kock), two-spotted spider mite ( Tetranychus urticae Koch), Kanzawa spinder mite ( Tetranychus kanzawai Kishida), etc.;
  • Pests of ERIOPHYDAE such as pink citrus rust mite ( Aculops pelekassi Keifor), pear rust mite ( Epitrimerus pyri Nalepa), dry bulb mite ( Aceria tulipae Keiter), pink tea mite ( Acaphylla theae watt), etc.;
  • Pests of TARSONEMIDAE such as broad mites ( Polyphagotarsonemus lotus Banks), cyclamen mite, strawberry mite ( Steneotarsonemus pallidus Banks), etc.;
  • Pests of ACARIDAE such as mold mite, copra mite, forage mite ( Tyrophagus putrescetiae Schrank), bulb mite ( Rhizoglyphus robini Claparede), etc.;
  • Pests of VARROIDAE such as bee brood mite ( Varroa jacobsoni Oudemans), etc.;
  • Pests of Ixodidae such as bull ticks ( Boophilus microplus Canestrini), ( Haemaphysalis longicornis Neumann), etc.;
  • Nematodes such as southern root-knot nematode ( Meloidogyne incognito Kofoid et White), northern root-knot nematode ( Meloidogyne hapla Chitwood), Cobb root-lesion nematode ( Pratylenchus penetrous Cobb), walnut root-lesion nematode ( Pratylenchus vulnus Allen et Jensen), potato cyst nematode ( Globodera rostochiensis Wollenweber), pine wood nematode ( Bursaphelenchus xylophilus Steiner et Buhrer), etc.;
  • Mollusca such as apple snail ( Pomacea canaliculata Lamarck), ( Incilaria pilineata Benson), ( Acusta despecta sieboldiana Pfeiffer), ( Euhadra peliomphala Pfeiffer), pillbug ( Armadillidium vulgare Latreille), etc.;
  • Crustaceans such as pillbug ( Armadillidium vulgare Latreille), etc.
  • the plant diseases to be controlled by the compounds of the present invention are as follows:
  • Blast Pyricularia oryzae
  • Helminthosporium leaf spot Cochliobalus miyabeanus
  • Sheath blight Rhizoctonia solani
  • Powdery mildew Erysiphe graminis f. sp. hordei, f. sp. tritici
  • Leaf stripe Pyrenophora graminea
  • Net blotch Pyrenophora teres
  • Fusarium blight Gibberella zeae
  • yellow rust black stem rust and brown rust
  • Puccinia striijormis P. graminis, P. recondita and P. hondei
  • Snow blight and snow mold Typhula sp., Micronectriella nivais
  • Loose smut Ustilago tritici, U.
  • Blossom blight Sclerotinia mali
  • Canker Valsa mali
  • Powder mildew Podosphaera leucotricha
  • Alternaria leaft spot Alternaria mali
  • Scab Yenturia inaequalis
  • Brown rot Sclerotinia cinerea
  • Scab Cladosporium carpophilum
  • Phomopsis rot Phomopsis sp.
  • Downy mildew Pseudoperenospora cubensis ), Anthracnose ( Colletotrichum lagenarium ), Powdery mildew ( Sphaerotheca fuliginea ), and Gummy stem blight ( Mycosphaerella melonis ) of cucurbit.
  • Late blight ( Phytophthora injestans ), Early blight ( Alternaria solani ) and Leaf mold ( Cladosporium fulvam ) of tomato.
  • Alternaria leaft spot Alternaria japonica
  • white spot Cerocosporella brassicae
  • Rust Puccinia allii
  • Anthracnose Collectorichum lindemuthianum ) of kidney bean.
  • Leaf spot Mycosphaerella personatum
  • Brown leaf spot Cercospora arachidicola
  • Powdery mildew ( Sphaerotheca humuli ) of strawberry
  • Leaf spot Septoria chrysanthemiindici
  • Rust Puccinia horiana
  • Sclerotinia rot Sclerotinia sclerotiorum ) of various kinds of crops.
  • the compounds of the present invention are effective in preventing the attachment of aquatic organisms, even at extremely low concentrations.
  • Aquatic organisms to which the invention is directed are, for example, shellfishes and algae, such as mussel, barnacle, oyster, hydrozoan, hydra, Serpula, ascidian, seamoss, Bagula, mud pond snail, sea lettuce, green lever, Ectocarpus, etc.
  • the compounds of the present invention can effectively eztertninete various pests and phytopathogenic microbes of, for example, Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Temitidae, and also mites and louses, even when used at low concentrations.
  • the compounds of the invention are effective in preventing the attachment of various aquatic organisms living in sea water and fresh water to aquatic constructions, etc.
  • the compounds of the present invention contains useful compounds that have few negative influences on mammals, fishes, shellfishes and useful insects.
  • L represents a suitable leaving group, such as a chlorine atom, a bromine atom, an iodine atom, an alkoxy group having from 1 to 4 carbon atoms, a phenoxy group, an alkylsulfonyloxy group having from 1 to 4 carbon atoms, a benzenesulfonyloxy group, a toluenesulfonyloxy group, a phenoxy group, a 1-pyrazolyl group or a 1-imidazolyl group; L′ represents a halogen atom; and alkyl represents an alkyl group preferably having from 1 to 4 carbon atoms.
  • Method A in (Scheme 1) is to react an acetonitrile derivative of formula (3) with an acid chloride, ester or amide of formula (4) or with an acid anhydride of formula (5) to give compounds (1′) of the present invention.
  • the compound (1′) of the invention is optionally reacted with an alkyl halide, an alkyl sulfonate, a trimethylsilyl halide, a sulfonyl chloride, a sulfamoyl chloride, a thiocarbamoyl chloride, an acid chloride or an ester of formula (8) to be converted into compounds (1) of the invention.
  • the compound (1′) is reacted with a dihydropyran, an isocyanate or a thioisocyanate to give the compounds (1).
  • Method A if the compound of formula (4) or (5) is used in an excessive amount, the compounds (1) can be directly obtained without isolating the compounds (1′).
  • compounds (1′) may be produced according to Method B.
  • Method B is to react a heterocyclic compound of formula (6) with a halogenocyanoketone derivative of formula (7) to give compounds (1′) of the invention.
  • compounds (1′) may be produced according to Method C.
  • Method C is to react a cyanoacetic acid derivative of formula (9) with a heterocyclic compound of formula (10) to give compounds (1′) of the invention.
  • the compound of formula (9) will be prepared by reacting an acetonitrile derivative of formula (3), such as that used in Method A, with a carbonic acid ester in the presence of a base.
  • Method D in (Scheme 2) is to react a compound of formula (11) with an acid chloride, ester or amide of formula (4) or with an acid anhydride of formula (5) to give the compounds (1′) of the present invention.
  • the compound (1′) of the invention is optionally reacted with an alkyl halide, an alkyl sulfonate, a trimethylsilyl halide, a sulfonyl chloride, a sulfamoyl chloride, a thiocarbamoyl chloride, an acid chloride or an ester of formula (8) to be converted into the compounds (1) of the invention.
  • the compound (1′) is reacted with a dihydropyran, an isocyanate or a thioisocyanate to give the compounds (1).
  • Method A if the compound of formula (4) or (5) is used in an excessive amount, the compounds (1) can be directly obtained without isolating the compounds (1′).
  • Method E is to react a heterocyclic compound of formula (6) with a compound of formula (12) in the presence of a base to give compounds (1′) of the-invention.
  • the compounds (1′) may be produced according to Method F.
  • Method F is to react a compound of formula (13) with a heterocyclic compound of formula (10) through dealcoholation to give the compounds (1′) of the invention.
  • the compound of formula (13) will he prepared by reacting a compound of formula (11), such as that used in Method D, with a carbonic acid ester in the presence of e base.
  • the compounds (1′) where E is an alkoxycarbonyl group may be hydrolyzed, decarbozylated and halogenated to give the compounds of the invention where E is a halogen atom.
  • the compounds of the invention where E is a halogen atom may be reacted with a nucleophilic reagent corresponding to E (e.g., triester phosphites, alkyl mercaptans, thiophenols, metal acerylides, metal cyanides, metal azides, nitrites) to give different compounds of the invention.
  • the compounds to be obtained through decarboxylation of the compounds (1′) where E is an alkoxycarbonyl group may be reacted with an electrophilic reagent under basic conditions to give the compounds of the invention.
  • the processes of (Scheme 1) and (Scheme 2) are preferably effected in the presence of a base.
  • the base to be used includes, for example, alkali metal alkoxides such as sodium ethoxide, sodium methoxide and t-butoxy potassium; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; organic bases such as triethylamine, pyridine and DBU; organic lithium compounds such as butyl lithium; lithium amides such as lithium diisopropylamide and lithium bistrimethylsilylamide; and sodium hydride.
  • the reactions of (Scheme 1) and (Scheme 2) may be effected in a solvent that is inert to the reaction.
  • the solvent includes, for example, lower alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene and toluene; etherd such as diethyl ether, tetrahydrofuran, 1,4-diozane, 1,2-dimethoxyethane and 1,2-diethoxyethane; halogenated hydrocarbons such as methylene chloride, chloroform and 1,2-dichloroethene; amides such as dimethylformamide and dimethylacetamide; acetonitrile; dimethylsulfoxide; and mixed solvents of these.
  • reaction temperature may be freely settled within a range between ⁇ 30° C. and 200° C. Preferably, the reaction temperature falls between 0° C. and 150° C., or between 0° C. and the boiling point of the solvent if used.
  • the base may be used in an amount of from 0.05 to 10 equivalents, preferably from 0.05 to 3 equivalents, of the reaction substrate.
  • the compounds of the present invention may be separated from reaction mixtures according to any ordinary methods. If the purification of the compounds of the invention is needed, they can be separated and purified by any ordinary methods of, for example, recrystallization or column chromatography.
  • those having an asymmetric carbon atom include optically-active compounds of (+) forth and ( ⁇ ) form.
  • a benzyl halide, a benzyl alkylsulfonate, a benzyl arylsulfonate, a halomethyl-heterocyclic compound, an alkylsulfonyloxymethyl-heterocyclic compound or an arylsulfonyloxymethyl-heterocyclic compound of formula (14) is reacted with a suitable cyanating reagent to give compounds (3).
  • a phenylacetic acid derivative or a heterocyclic acetic acid derivative is converted into the corresponding amide derivative, which is then dehydrated to give compounds (3).
  • a heterocyclic derivative (6) where the nitrogen atom of Q is unsubstituted is reacted with a haloacetonitrile derivative in the presence of a base.
  • the compound (6) is reacted with a compound (18) in the presence of a base to give a compound (17), said compound (18) being obtained through halogenation of a cyanoacetate, and thereafter the compound (17) is hydrolyzed and decarbozylated to obtain the compounds (3).
  • the compounds (11) to be used in (Scheme 2) can be produced in the same manner as in the production of the compounds (3) mentioned above.
  • the compounds (7) to be used in (Scheme I) can be produced by condensing a benzoic acid halide or heterocyclic carboxylic acid halide with a cyanoacetate in the presence of a base followed by halogenating the resulting condensate.
  • halomethyl-heterocyclic compounds, alkylsulfonyloxymethyl-heterocyclic compounds and arylsulfonyloxymethyl-heterocyclic compounds can be derived from heterocyclic methane derivatives or heterocyclic carboxylate derivatives that are produced according to ordinary methods (see Alan R. Katritzky, and Charles W. Rees; Comprehensive Heterocyclic Chemistry, Vol. 2, Vol. 3, Vol. 4, Vol. 5 or Vol. 6).
  • Q is an oxazol-4-yl or thiazol-4-yl group
  • a carboxylic acid amide or thioamide can be reacted with 1,3-dichloro-2-propanone.
  • Me methyl group
  • Et ethyl group
  • Pr propyl group
  • Bu butyl group
  • Pen pentyl group
  • Hex hexyl group
  • Hep heptyl group
  • Oct cetyl group
  • Dec decyl group
  • Ph phenyl group
  • n normal, is iso
  • sec secondary
  • t tertiary
  • c cyclo.
  • the compounds of the present invention are used as pesticides, in general, they can be mixed with a suitable carrier, for example a solid carrier, such as clay, talc, bentonite, diatomaceous earth or white carbon, or a liquid carrier such as water, alcohols (e.g., isopropanol, butanol, benzyl alcohol, furfuryl alcohol), aromatic hydrocarbons (e.g., toluene, xylene), ethers (e.g., anisole), ketones (e.g., cyclohexanone, isophorone), esters (e.g., butyl acetate), acid amides (e.g., N-methylpyrrolidone) or halogenated hydrocarbons (e.g., chlorobenzene), optionally along with other additives such as surfactant, emulsifier, dispersing agent, penetrating agent, spreading agent, thickener, anti-freezing agent, anti-caking agent and stabilize
  • the compounds of the present invention are used as agricultural chemicals, they can be combined with any other herbicides, various insecticides, acaricides, nematecides, fungicides, plant growth regulators, synergists, fertilizer and soil improvers, when they are formulated into preparations for practical use or while they are actually used through spraying or the like.
  • the combination of the compounds of the invention and other agricultural chemicals or plant hormones will be advantageous in that the amount of the chemicals to be used can be reduced thereby resulting in the reduction of the costs for the treatment, and that the mixed chemicals exhibit synergistic effects to broaden the insecticidal spectrum while displaying higher pesticidal activities.
  • the compounds of the invention can be combined with e plurality of known agricultural chemicals.
  • the agricultural chemicals capable of being combined with the compounds of the invention for example, the compounds described in Farm Chemicals Handbook, 1994 are referred.
  • Fungicide acibenzolar, ampropyfos, anilazine, azaconezole, azoxystrobin, benalaxyl, benodanil, benomyl, benzamecril, binapacryl, biphenyl, bitertanol, bethoxazine, Bordeaux mixture, blesticidin-S, bromoconazole, bupirimate, buthiobate, calcium polysulfide, captafol, captan, copper oxychloride, caryropamid, carbendazim, carboxin, chinomethionat, chlobrnthiazone, chlorfenazol, chloroneb, chlorothalonil, chlozolinete, cufraneb, cymoxanil, cyproconazol, cyprodinil, cyprofuram, debacarb, dichlorophen, diclobutrazol, dichlofluanid
  • Bacteriazide streptomycin, oxyterracycline, oxolinic acid.
  • Nematicide aldoxycarb, cadusafos, fosthiazate, fosthietan, oxemyl, fenamiphos.
  • Acaricide acequinocyl, acrinathrin, amitraz, bifenazate, bromopropylate, chinomethionat, chlorobezilate, clofentezine, cyhexatine, dicofol, dirnochlor, etoxazole, frnazaquin, fenbutatin oxide, fenpropathrin, fenproximate, halfenprox, hexythiazox, milbemectin, phenisobromolate, polynactins, propargite, pyridaben, pyrimidifen, tebufenpyrad, tetradifon.
  • Insecticide abamectin, acephate, ecetamipirid, alanycarb, azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin, Batillus thuringiensis , buprofezin, butocarboxim, carberyl, carbofuran, carbosulfan, cartap, chlorfenapyr, chlorpyrifos, chlorfenvinphos, chlorfluazuron, clothianidin, chromafenozide, chlorpyrifos-methyl, cyanox, cycloprothrin, cyfluthrin, beta-cyfluthrin, cypermethrin, cyromezine, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diecloden, dichlorvos, diflubenzuron
  • the dose of the compounds of the present invention varies depending on an application place, an application time, an application method, cultivation crops, etc. In general, it may be between approximately 0.005 kg and 50 kg per hectare (ba) in terms of the amount of the active ingredient.
  • the others include, for example, anti-caking agent, etc.
  • the others include, for example, anti-freezing agent, thickener, etc.
  • the compounds of the present invention are used as an agent for preventing the attachment of aquatic organisms, they may be formulated into various preparations of, for example, coating paints, solutions, emulsions, pellets or flakes to be applicable to various objects.
  • the preparations can be used in any ordinary manners of, for example, coating, spraying, dipping, adding to water or installing in water.
  • To prepare such coating paints, solutions, emulsions and others, employable are any ordinary methods.
  • the compounds may also be used, for example, by incorporating them into ropes or fiber materials for fishing nets in the stage of preparing the ropes or fiber materials to thereby making them have the ability to prevent the attachment of aquatic organisms thereto.
  • the agents for preventing the attachment of aquatic organisms according to the present invention can be used either singly or as combined with any other agents for preventing the attachment of aquatic organisms.
  • the compounds of the invention may be mixed with film-forming agents to prepare coatings.
  • the film-forming agents include oil varnishes, synthetic resins, artificial rubbers, etc. If desired, solvents, pigments and others can be added to the coatings.
  • the uppermost limit of the concentration of the compounds of the invention to be therein is not specifically limited, provided that the resulting coatings can form film, but may be from 1 to 50% by weight, preferably from 5 to 20% by weight, relative to the weight of the antifouling coatings.
  • the compounds of the invention may be dissolved in solvents along with film-forming agents to prepare solutions.
  • the film-forming agents include synthetic resins, artificial rubbers, natural resins, etc.
  • the solvents include xylene, toluene, cumene, methyl ethyl ketone, methyl isobutyl ketone, acetone, etc. If desired, additives such as plasticizer may be added to the solutions.
  • the uppermost limit of the concentration of the compounds of the invention to be therein is not specifically limited, provided that the compounds are dissolved to give solutions, but may be from 1 to 50% by weight, preferably from 5 to 30% by weight, relative to the weight of the solutions.
  • surfactants are added to the compounds of the invention to prepare the intended emulsions according to ordinary methods of preparing general emulsions.
  • the type of the surfactants to be used is not specifically limited.
  • the uppermost limit of the concentration of the compounds of the invention to be therein is not specifically limited, provided that the compounds are emulsified to give emulsions, but may be from 1 to 50% by weight, preferably from 5 to 30% by weight, relative to the weight of the emulsions.
  • the agents for preventing the attachment of aquatic organisms of the present invention are used in the form of pellets or flakes
  • the constitutive components of the compounds of the invention and optionally plasticizers, surfactants and others are added to the base of hydrophilic resins which are solid at room temperature, such as polyethylene glycol in a solid form, and the resulting mixtures are shaped into pellets or flakes through melting molding, compression molding or the like.
  • the uppermost limit of the concentration of the compounds to be therein is not specifically limited, provided that the compounds can be shaped into pellets or flakes, but may be from 20 to 95% by weight, preferably from 30 to 90% by weight, relative to the weight of the pellets or flakes.
  • the reaction mixture was poured into ice water, acidified with diluted hydrochloric acid, extracted with ethyl acetate, and washed with saturated saline.
  • the resulting product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the residual product was purified through silica gel column chromatography to obtain the intended product from the fraction eluted with chloroform.
  • the resulting product was crystallized and washed with diethyl ether to obtain 0.86 g of 3-(1-methyl-3,5-dichloropyrazol-4-yl)-2-(2-phenylthiazol-4-yl)-3-hydroxyacrylonitrile.
  • the residual product was dissolved in a mixed solvent of 10 ml of water and 10 ml of dioxane, and 0.38 g of potassium hydroxide was added thereto and heated under reflux for 4 hours. After having been left to be at room temperature, this was acidified with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure.
  • reaction mixture was left to be at room temperature, and concentrated, and the resulting concentrate was purified through silica gel column chromatography (chloroform) and recrystallization (chloroform-diisopropyl ether) to obtain 2- ⁇ 3-(2,6-difluorophenyl)pyrazol-1-yl ⁇ -3-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)ethan-1-one (0.1 g). m.p.: 152-154° C.
  • Triethylamine (0.3 g) and pivalic acid chloride (0.23 g) were added in that order to a chloroform (25 ml) solution of Compound No. I-134 (0.47 g) at 0° C., and stirred at room temperature for 1 hour.
  • the resulting product was extracted with water and chloroform.
  • the organic layer was dried with anhydrous magnesium sulfate, concentrated, and purified through silica gel column chromatography (chloroform) to obtain the intended product, Compound No. I-135 (0.4 g).
  • Wettable Powder Compound No. I-1 of the invention 50 parts Zeeklite PFP (trade name, kaolin-type clay 43 parts manufactured by Zeeklite Mining Industries, Co., Ltd.) Solpol 5050 (trade name, anionic surfactant 2 parts manufactured by Toho Chemical Co., Ltd.) Runox 1000C (trade name, anionic surfactant 3 parts manufactured by Toho Chemical Co., Ltd.) Carplex #80 (anti-caking agent, trade name, 2 parts white carbon manufactured by Shionogi Pharmaceutical Co., Ltd.)
  • Granular wettable powder (Dry flowable): Compound No. I-1 of the invention 75 parts Isoban No. 1 (trade name, anionic surfactant 10 parts manufactured by Kuraray Isoprene Chemical Co., Ltd.) Vanilez N (trade name, anionic surfactant 5 parts manufactured by Sanyo Kokusaku Pulp Co., Ltd.) Carplex #80 (trade name, white carbon 10 parts manufactured by Shionogi Pharmaceutical Co., Ltd.)
  • the above-mentioned components were homogeneously mixed and ground, to which was added a small amount of water, stirred, mixed and kneaded. The resulting mixture was granulated and dried into granules, using an extrusion granulator.
  • the wettable powder, emulsion, flowable and dry flowable are diluted from 50 to 20000 times with water, and applied in an amount of from 0.005 to 50 kg/ha in terms of the active ingredient.
  • the above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms of the invention.
  • This agent can be used as a coating paint.
  • the above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms of the invention.
  • This agent can be used as a coating paint.
  • the above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms the invention.
  • This agent can be used as a coating paint.
  • the above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms of the invention.
  • This agent can be used as a coating paint.
  • Test Examples are to demonstrate the usefulness of the compounds of the present invention as pesticides.
  • a 5% emulsion (or 25% wettable powder) of a compound of the present invention was diluted with water containing a spreading agent to give a 500 ppm solution of the compound.
  • the stems and leaves of plants was dipped in a 500 ppm emulsion of a compound of the invention for about 10 seconds.
  • the thus-treated stems and leaves were put into glass cylinders, into which were released adults of green rice leafhoppers (Nephotettix cincticeps) that were resistant to organic phosphorous insecticides.
  • Each glass cylinder was covered with a perforated cover, and stored in a thermostatic chamber at 25° C. After 6 days passed, the insects in each cylinder were observed, and the mortality of the insects was determined according ot the sme equation as in Test Example 1.
  • Each compound was tested in that manner for two groups of cylinders. In this test, the following compounds exhibited morality of 80% or more.
  • Moistured filter paper was placed in each laboratory glass dish having an inner diameter of 3 cm, and a leaf cabbage having the same diameter as that of the dish was put on the filter paper.
  • Four female, apterous adults of green peach aphids (Myzus persicae) were put on the cabbage leaf.
  • a chemical sample (2.5 mg/cm 2 ) was sprayed over the dishes, using a rotary sprinkler.
  • the chemical solution herein was prepared by diluting a 5% emulsion (or 25% wettable powder) of a compound of the invention to 500 ppm with water containing a spreading agent. After 6 days passed, the insects in each cylinder were observed, and mortality of the insects (larvae and adults) was determined according to the following equation. Each compound was tested in that manner for two groups of dishes.
  • the leaves of cabbage were dipped in a 500 ppm aqueous emulsion of a compound of the invention for about 10 seconds. After having been dried in air, the thus-treated leaves were put into laboratory dishes. Ten (10) second larvae of diamond back moth (Plutella xylostella) were released in each dish. Each dish was covered with a perforated cover, and stored in a thermostatic chamber at 25° C. After 6 days passed, the insects in each dish were observed, and mortality of the insects was obtained according to the same equation as in Test Example 1. Each compound was tested in that manner for two groups of dishes. In this test, the following compounds exhibited mortality of 80% or more.
  • a 5% emulsion (or 25% wettable powder) of a compound of the present invention was diluted with water containing a spreading agent to give a 500 ppm solution of the compound.
  • the leaves of cucumbers were dipped in this chemical solution for about 10 seconds, dried in air, and put into a laboratory dish.
  • Ten (10) second instar nymphae of cucur-bit leaf beetles (Aulacophora femoralis) were released in each dish. Each dish was covered with a cover, and stored in a thermostatic chamber at 25° C. After 6 days passed, the insects in each dish were observed, and mortality of the insects was determined according to the same equation as in Test Example 1.
  • Each compound was tested in that manner for two groups of dishes.
  • kidney bean plants were punched into 3 cm-diameter discs, using a leaf punch, and put onto moistured filter paper in a 7 cm-diameter styrol cup.
  • Ten (10) larvae of two-spotted spider mites (Tetranychus urticae) were put to each leaf.
  • a 5% emulsion (or 25% wettable powder) of a compound of the invention was diluted with water containing a spreading agent to give a 500 ppm solution of the compound.
  • the solution was sprayed over each cup in an amount of 2 ml/cup, using a rotary sprinkler, and the cups were stored in a thermostatic chamber at 25° C. After 96 hours passed, the mites in each cup were observed, and mortality of the mites was determined according to the same equation as in Test Example 1.
  • Each compound was tested in that manner for two groups of cups.
  • a chemical solution obtained by diluting an emulsion of a compound of the invention to 500 ppm with water was sprayed on wheat plants (Norin No. 61) grown to 1.5- to 2.0-leaf in a pot having a diameter of 5.5 cm-diameter at a dose of 20 ml/pot using a spraygun.
  • a spore suspension (2 ⁇ 10 5 spore/ml) of leaf rust (brown rust) (Puccinia recondite) was sprayed over the plant-pots were placed overnight in an inoculation box having a temperature of 25° C. and a humidity of 95% or more. Then, the pots were put in a green house. After 7 days of the inoculation, a ratio of an infected and spored area formed to the leaf inoculated was measured, and a preventive value was calculated according to the following equation.
  • Preventive value [1 ⁇ (infected and spotted area ratio in treated region/infected and spotted area ratio in untreated region)] ⁇ 100
  • the present invention provides novel, non-toxic and non-persistent insecticides and fungicides, and provides agents for preventing the attachment of aquatic organisms having few influences on the ecosystem and causing little secondary pollution.

Abstract

Ethylene derivatives of formula (I):
Figure USRE038188-20030715-C00001
where Q is an unsubstituted or substituted phenyl or heterocyclic group, especially a 4-thiazolyl, 1- or 3-pyrazolyl, 1,3-oxazol-4-yl, phenyl or pyridyl group; E is a substituent such as a cyano group; A is a substituent such as a 4-pyrazolyl or thiazolyl group; and B is a substituent such as an alkylcarbonyl group. Agricultural chemicals and agents for preventing the attachment of aquatic organisms containing one or more such ethylene derivatives.

Description

This is a cont.-in-part of international application No. PCT/JP97/01449, filed Apr. 24, 1997.
BACKGROUND OF THE INVENTION
1. Field of the Art
The present invention relates to novel ethylene derivatives, and also to agricultural chemicals and agents for preventing the attachment of aquatic organisms containing said derivatives as an active ingredient. The agricultural chemicals as referred to herein include insecticides, acaricides, nematocides, herbicides and fungicides, etc., and are especially pesticides in the field of agriculture, horticulture, stock farming and sanitation. The agent for preventing the attachment of aquatic organisms are chemicals for preventing the attachment of harmful aquatic organisms such as shells and algae to fishing nets, the bottoms of ships, marine equipment such as buoys, marine constructions, circulating water systems in thermal and atomic power plants, inlet channels for heat exchanger cooling water in chemical industry, underwater constructions and reservoirs.
2. Description of the Related Art
For acrylonitrile derivatives, Japanese Patent Application Laid-Open No. Sho 53-92769 discloses the use of 2′-chloro-3-hydroxy-2-(4-phenyl-2-thiazolyl)-cinnamoyl nitrile as an insecticide; and International Patent Application Laid-Open No. WO-95/29591 discloses its use as an aquatic adhesion inhibitor. Japanese Patent Application Laid-open No. Sho 60-11452 discloses the use of 2-(4-chlorophenyl)-3-(3-pyridyl)-3-oxopropionitrile as a herbicide and Japanese Patent Application Laid-open No. Sho 60-11401 discloses its use as a fungicide.
With the long-term use of insecticides and fungicides, recently, some pests have become resistant to chemicals and are often difficult to exterminate with conventional insecticides and fungicides. In addition, some insecticides are highly toxic and are prone to remain long, without being decomposed, to destroy the ecosystem. Accordingly, it is always expected to develop novel, low-toxic and low-persistent insecticides and fungicides.
On the other hand, in order to prevent the adhesion and growth of marine and freshwater aquatics, it is used antifouling coatings comprising organic tin compounds such as bis(tributyltin) oxide or copper compounds such as copper sulfate and cuprous oxide. However, organic tin compounds are highly toxic, though being effective in preventing the adhesion of aquatics, and are especially prone to accumulate in the bodies of fishes and shellfishes. As so promoting the environmental pollution, the use of those compounds is now under legal controls. Copper compounds are widely used in antifouling coatings for inlet channels and for the bottoms of ships. However, like tin compounds, copper compounds contain a copper as a heavy metal. Therefore, the use of copper compounds will bring about the environmental pollution in future, and agents for preventing the attachment of aquatic organisms comprising such copper compounds are not preferred. Under the above-mentioned situation, it has been desired agents for preventing the attachment of aquatic organisms that have few influences on the ecosystem and bring about little secondary pollution.
SUMMARY OF THE INVENTION
In order to solve the above-mentioned problems, the present inventors have assiduously studied to develop agricultural chemicals and agents for preventing the attachment of aquatic organisms which can exhibit excellent pesticidal activities even when used in small amounts, and which have few negative influences on non-targeted organisms such as mammals, fishes and useful insects, and, as a result, have found that the compounds mentioned hereinunder are highly safe and have excellent pesticidal activities and activities for preventing the attachment of aquatic organisms. On the basis of these findings, the present inventors have completed the present invention.
DETAILED DESCRIPTION OF THE INVENTION
Specifically, the present invention provides the following [1] to [25]
[1] Ethylene derivatives of a formula (I):
[wherein;
Q represents a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, imidazolinone, imidazolidinedione, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
A represents a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
provided that, (a) when Q is a thienyl group optionally substituted by R, a furyl group optionally substituted by R, a quinolyl group optionally substituted by R, or an isoquinolyl group optionally substituted by R, then A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(b) when Q is a 2-thiazolyl group optionally substituted by R, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(c) when Q is a pyridyl group optionally substituted by R, then A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(d) when Q is an isothiazolyl group optionally substituted by R, a 1,2,3-triazolyl group optionally substituted by R, or a benzoxazolyl group optionally substituted by R, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(e) when Q is a 1,2,4-triazolyl group optionally substituted by R, then A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(f) when Q is a benzothiazolyl group optionally substituted by R, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(g) when Q is a benzimidazolyl group optionally substituted by R, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(h) when Q is a phenyl group optionally substituted by G, then A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
(i) when Q is a naphthyl group optionally substituted by G, than A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3SCH2, CH3OC2H4OCH2, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C4 alkyl group substituted by a benzoyl group optionally substituted by a halogen or a C1-C4 alkyl group, a tetrahydropyranyl group, (CH3)3Si, a C1-C4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C1-C4 alkyl group, —SO2CF3, a C1-C4 monoalkylaminosulfonyl group, a C2-C8 dialkylaminosulfonyl group, a phenylaminosulfonyl group, a C2-C5 monoalkylaminothiocarbonyl group, a C3-C9 dialkylaminothiocarbonyl group, a C2-C5 cyanoalkyl group, a C3-C9 alkoxycarbonylalkyl group, —C(═O)T1, —P(═O)T2T3, —P(═S)T2T3, an alkali metal atom, an alkaline earth metal atom, or NHT4T5T6;
provided that, when Q is a 2-thiazolyl or 2-benzothiazolyl group, then B is a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3SCH2, CH3OC2H4OCH2, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C4 alkyl group substituted by a benzoyl group optionally substituted by a halogen or a C1-C4 alkyl group, a tetrahydropyranyl group, (CH3)3Si, a C1-C4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C1-C4 alkyl group, —SO2CF3, a C1-C4 monoalkylaminosulfonyl group, a C2-C8 dialkylaminosulfonyl group, a phenylaminosulfonyl group, a C2-C5 monoalkylaminothiocarbonyl group, a C3-C9 dialkylaminothiocarbonyl group, a C2-C5 cyanoalkyl group, a C3-C9 alkoxycarbonylalkyl group, —C(═O)T1, —P(═O)T2T3, or —P(═S)T2T3;
E represents a heterocyclic group optionally substituted by a C1-C4 alkyl or C1-C4 haloalkyl group—(said heterocyclic group being a 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,3,4-oxadiazol-2-yl, 5-tetrazolyl, 2-oxazolinyl or 1,2,4,5-tetrazin-3-yl group) - or represents a halogen, a C2-C4 alkynyl group, a phenylethynyl group optionally substituted by Z, a C1-C4 haloalkyl group, CN, an isonitrile group, NO2, N3, CHO, a C2-C5 alkylcarbonyl group, a C2-C5 alkoxycarbonyl group, a C3-C5 alkenyloxycarbonyl group, a C2-C4 alkylaminocarbonyl group, a C3-C9 dialkylaminocarbonyl group, a benzoyl group optionally substituted by Z, an aminothiocarbonyl group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a phenylsulfenyl group optionally substituted by Z, a phenylsulfinyl group optionally substituted by Z, a phenylsulfonyl group optionally substituted by Z, —P(═O)T2T3, or —P(═S)T2T3.
G is a substituent freely selected from a halogen atom, a C1-C10 alkyl group, a C2-C4 cyanoalkyl group, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C6 halocycloalkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, a C1-C10 alkoxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C1-C4 haloalkoxy group, a C2-C6 haloalkenyloxy group, a C2-C6 haloalkynyloxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C2-C6 alkenylsulfenyl group, a C2-C6 alkenylsulfinyl group, a C2-C6 alkenylsulfonyl group, a C2-C6 alkynylsulfenyl group, a C2-C6 alkynylsulfinyl group, a C2-C6 alkynylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, a C2-C6 haloalkenylsulfenyl group, a C2-C6 haloalkenylsulfinyl group, a C2-C6 haloalkenylsulfonyl group, a C2-C6 haloalkynylsulfenyl group, a C2-C6 haloalkynylsulfinyl group, a C2-C6 haloalkynylsulfonyl group, CHO, NO2, CN, —NU1U2, OH, a naphthyl group, a methoxy group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C2-C7 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a C2-C4 alkylcarbonyl group, a C2-C4 haloalkylcarbonyl group, a C2-C5 alkylcarbonyloxy group, a C2-C5 haloalkylcarbonyloxy group, a C3-C7 dialkylaminocarbonyloxy group, a phenyl group optionally substituted by Z, a phenoxy group optionally substituted by Z, a benzoyl group optionally substituted by Z, a pyridyl group optionally substituted by Z, a pyridyloxy group optionally substituted by Z, a thienyl group optionally substituted by Z, a methylenedioxy group as bonded at the adjacent substituting positions, a halomethylenedioxy group as bonded at the adjacent substituting positions, and —N═CT7T8 (in which T7 and T8 each independently represent H, or a phenyl, benzyl or C1-C6 alkyl group, or T7 and T8, together with the carbon atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring), (provided that when the the substituent is two or more, then said substituents may be the same or different), and the number of the substituent, G, is 1, 2, 3 or 4; or G is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring;
R is a substituent freely selected from a halogen atom, a C1-C10 alkyl group, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C2-C8 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C6 halocycloalkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, a C1-C6 alkoxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C1-C4 haloalkoxy group, a C2-C6 haloalkenyloxy group, a C2-C6 haloalkynyloxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C2-C6 alkenylsulfenyl group, a C2-C6 alkenylsulfinyl group, a C2-C6 alkenylsulfonyl group, a C2-C6 alkynylsulfenyl group, a C2-C6 alkynylsulfinyl group, a C2-C6 alkynylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, a C2-C6 haloalkenylsulfenyl group, a C2-C6 haloalkenylsulfinyl group, a C2-C6 haloalkenylsulfonyl group, a C2-C6 haloalkynylsulfenyl group, a C2-C6 haloalkynylsulfinyl group, a C2-C6 haloalkynylsulfonyl group, NO2, CN, —NU1U2, a phenoxy group, OH, a naphthyl group, a C2-C7 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a C2-C4 alkylcarbonyl group, a C2-C5 alkylcarbonyloxy group, a C2-C5 haloalkylcarbonyloxy group, a benzoyl group optionally substituted by X, a phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, a thienyl group optionally substituted by X, and —N═CT7T8, (provided that when the substituent is two or more, then said substituents may be the same or different), and the number of the substituents, R, is 1, 2, 3 or 4; or R is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring;
Y is a substituent freely selected from a halogen atom, a C1-C10 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C1-C4 haloalkoxy group, a C2-C6 haloalkenyloxy group, a C2-C6 haloalkynyloxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C2-C6 alkenylsulfenyl group, a C2-C6 alkenylsulfinyl group, a C2-C6 alkenylsulfonyl group, a C2-C6 alkynylsulfenyl group, a C2-C6 alkynylsulfinyl group, a C2-C6 alkynylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, a C2-C6 haloalkenylsulfenyl group, a C2-C6 haloalkenylsulfinyl group, a C2-C6 haloalkenylsulfonyl group, a C2-C6 haloalkynylsulfenyl group, a C2-C6 haloalkynylsulfinyl group, a C2-C6 haloalkynylsulfonyl group, NO2, CN, —NU1U2, OH, a C2-C7 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a C2-C6 alkylcarbonyloxy group, a C2-C5 haloalkylcarbonyloxy group, a C3-C7 dialkylaminocarbonyloxy group, a phenyl group optionally substituted by X, and —N═CT7T8 (in which T7 and T8 each independently represent H, or a phenyl, benzyl or C1-C6 alkyl group, or T7 and T8 may, together with the carbon atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring), (provided that when the substituent is two or more, then said substituents may be the same or different), and the number of the substituent, Y, is 1, 2, 3 or 4; or Y is an alkylene groupas bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring;
W is a substituent freely selected from a halogen atom, a C1-C6 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkenyloxy group, a C2-C4 haloalkenyloxy group, a C2-C4 alkenylsulfenyl group, a C2-C4 alkenylsulfinyl group, a C2-C4 alkenylsulfonyl group, a C2-C4 haloalkenylsulfenyl group, a C2-C4 haloalkenylsulfinyl group, a C2-C4 haloalkenylsulfonyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C2-C4 alkynyloxy group, a C2-C4 haloalkynyloxy group, a C2-C4 alkynylsulfenyl group, a C2-C4 alkynylsulfinyl group, a C1-C4 alkynylsulfonyl group, a C2-C4 haloalkynylsulfenyl group, a C2-C4 haloalkynylsulfinyl group, a C2-C4 haloalkynylsulfonyl group, NO2, CN, a formyl group, a C2-C6 alkoxycarbonyl group, a C2-C6 alkylcarbonyl group, a C2-C6 haloalkylcarbonyl group, a C2-C6 alkylcarbonyloxy group, and —NU1U2, (provided that when the substituent is two or more, then said substituents may be the same or different), and the number of the substituent, W, is 1, 2, 3 or 4;
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C6 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C3-C6 halocycloalkyl group, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, a cycloalkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C3 alkyl group, a cyclopropyl group substituted by both a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group and a C1-C4 alkyl group, a C3-C4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen or a C1-C4 alkoxy group, and a halogen, a cyclopropyl group substituted by both a C2-C4 alkenyl group optionally substituted by a halogen, and a C1-C4 alkyl group, a C2-C4 alkenyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a C2-C5 alkenyloxy group, a C3-C6 cycloalkoxy group optionally substituted by a C1-C3 alkyl group, a benzyloxy group, a C2-C6 alkoxycarbonyl group, —NU1U2, a phenylamino group, a phenyl group optionally substituted by Z, a phenoxy group optionally substituted by Z, a phenylthio group optionally substituted by Z, a naphthyl group optionally substituted by Z, or a 5-membered or 6-membered heterocyclic group optionally substituted by Z, (said heterocyclic group being selected from thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl and 3(2H)-pyridazinone groups);
T2 and T3 each independently represent OH, a phenyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, or a C1-C4 alkylsulfenyl group;
T4, T6 and T8 each independently represent H, a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, or a benzyl group; or any two of T4, T5 and T6 may, together with the nitrogen atom to which they are bonded, form a 5-, 6-, 7- or 8-membered cyclic group optionally containing oxygen, nitrogen and/or sulfur atoms;
X and Z are independently substituents as freely selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C2-C5 alkenylsulfenyl group, a C2-C5 alkenylsulfinyl group, a C2-C5 alkenylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, NO2, CN, CHO, OH, —NU1U2, a phenyl group, a phenoxy group, and a C2-C5 alkoxycarbonyl group, (provided that when the substituent is two or more, then said substituents may be the same or different), and the number of the substituent, X and Z, is 1, 2, 3, 4 or 5 each;
T7 and T8 each independently represent H, or a phenyl, benzyl or C1-C6 alkyl group, or T7 and T8 may, together with the carbon atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring; and
U1 and U2 each independently represent H, a C1-C6 alkyl, C2-C, alkylcarbonyl, phenyl or benzyl group, or U1 and U2 may, together with the nitrogen atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring.
[2] Ethylene derivatives of the above-mentioned 1], in which;
Q is a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R, (said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl, pyrazolinyl, imidazolinyl, imidazolinone or imidazolidinedione group;
A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, said heterocyclic group being a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl or imidazolinyl group;
B is H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H4OCH2, a C1-C4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C1-C4 alkyl group, —SO2CF3, a C1-C8 dialkylaminosulfonyl group, a C2-C9 dialkylaminothiocarbonyl group, a C3-C9 alkoxycarbonylalkyl group, —C(═O)T1, —P(═O)T2T8, —P(═S)T2T3, an alkali metal atom, an alkaline earth metal atom, or NHT4T5T6; and
T1 is a C1-C2 O alkyl group, a C2-C6 alkenyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C3-C6 halocycloalkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, a cycloalkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a cyclopropyl group substituted by both a phenyl optionally substituted by a halogen or a C1-C4 alkyl group, and a C1-C4 alkyl group, a C3-C4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen or a C1-C4 alkoxy group and a halogen, a cyclopropyl group substituted by both a C2-C4 alkenyl group optionally substituted by a halogen and a C1-C4 alkyl group, a C2-C4 alkenyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a C2-C5 alkenyloxy group, a C3-C6 cycloalkoxy group optionally substituted by a C1-C3 alkyl group, a benzyloxy group, a C2-C6 alkoxycarbonyl group, a phenyl group optionally substituted by Z, a phenoxy group optionally substituted by Z, a phenylthio group, a naphthyl group, or a heterocyclic group optionally substituted by Z, said heterocyclic group being selected from thienyl, furyl, oxazolyl, thiazolyl, pyrazolyl and pyridinyl groups.
[3] Ethylene derivatives of the above-mentioned [2], in which;
Q is a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R, said heterocyclic group being
Figure USRE038188-20030715-C00002
Figure USRE038188-20030715-C00003
Figure USRE038188-20030715-C00004
Figure USRE038188-20030715-C00005
Figure USRE038188-20030715-C00006
Figure USRE038188-20030715-C00007
Figure USRE038188-20030715-C00008
A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, said heterocyclic group being
Figure USRE038188-20030715-C00009
Figure USRE038188-20030715-C00010
Figure USRE038188-20030715-C00011
Figure USRE038188-20030715-C00012
Figure USRE038188-20030715-C00013
Figure USRE038188-20030715-C00014
Figure USRE038188-20030715-C00015
provided that, when (a) Q is any of Q-1, Q-2, Q-3 or Q-4, then A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),
(b) when Q is Q-12, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),
(c) when Q is any of Q-52, Q-53 or Q-54, then A is a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-60, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),
(d) when Q is any of Q-23, Q-24, Q-43, Q-44, Q-45, Q-46 or Q-49, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),
(e) when Q is any of Q-37, Q-38, Q-39, Q-40, Q-41 or Q-42, then A is a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),
(f) when Q is a phenyl group optionally substituted by G, then A is a heterocyclic group optionally substituted by Y, said heterocyclic group being any of A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75,
(g) when Q is a naphthyl group optionally substituted by G, then A is a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of A-1, A-2, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75,
R1 is selected from a halogen atom, a C1-C10 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C2-C6 alkenyloxy group, NO2, CN, —NU1U2, OH, a C2-C7 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a C2-C4 alkylcarbonyl group, a phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, a thienyl group optionally substituted by X, and —N═CT7T8 (in which T7 and T8 each independently represent H, a phenyl, benzyl or C,-C, alkyl group, or T7 and T8 may, together with the carbon atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring); or may, together with the adjacent R, form a 5-, 6-, 7- or 8-membered ring as an alkylene group
Y1 is selected from a halogen atom, a C1-C10 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C2-C6 alkenyloxy group, NO2, CN, —NU1U2, OH, a C2-C7 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a phenyl group optionally substituted by X, and —N═CT7T8 (in which T7 and T8 each independently represent H, or a phenyl, benzyl or C1-C6 alkyl group, or T7 and T8 may, together with the carbon atom to which they are bonded), form a 5-, 6-, 7- or 8-membered ring); or may, togeher with the adjacent Y1, form a 5-, 6- 7- or 8-membered ring an alkylene group;
X is a substituent of which the number is from 1 to 4 and which is freely selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C2-C5 alkenylsulfenyl group, a C2-C5 alkenylsulfinyl group, a C2-C5 alkenylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, NO2, CN, CHO, OH, —NU1U2, a phenyl group, a phenoxy group, and a C2-C5 alkoxycarbonyl group, (provided that when the number of the substituent, X, is two or more then said substituents may be the same or different);
Z is a substituent of which the number is from 1 to 4 and which is freely selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 alkenylsulfenyl group, a C1-C4 alkenylsulfinyl group, a C1-C4 alkenylsulfonyl group, NO2, CN, —NU1U2, a phenyl group, a phenoxy group, and a C2-C5 alkoxycarbonyl group, (provided when the number of the substituent, Z, is two or more, said substituents may be the same or different);
m indicates the number of the substituents, and is 0, 1, 2 or 3;
n indicates the number of the substituents, and is 0, 1, 2, 3, or 4;
p indicates the number of substituents, and is 0, 1 or 2;
q indicates the number of the substituents, and is 0 or 1;
(provided that when m, n and p each are an integer of 2 or more, the substituents may be the same or different).
[4] Ethylene derivatives of the above-mentioned [2], in which E is CN.
[5] Ethylene derivatives of the above-mentioned [5], in which E is CN.
[6] Ethylene derivatives of the above-mentioned [2], in which E is a heterocyclic group optionally substituted by a C1-C4 alkyl or C1-C4 haloalkyl group—(said heterocyclic group being a 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl or 1,3,4-oxadiazol-2-yl group)—or is a halogen atom, a C2-C4 alkynyl group, a phenylethynyl group optionally substituted by Z, a C1-C4 haloalkyl group, CN, NO2, N3, CHO, a C2-C5 alkylcarbonyl group, a C2-C5 alkoxycarbonyl group, a C2-C4 alkylaminocarbonyl group, a C3-C9 dialkylaminocarbonyl group, a benzoyl group optionally substituted by Z, an aminothiocarbonyl group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a phenylsulfenyl group optionally substituted by Z a phenylsulfinyl group optionally substituted by Z, a phenylsulfonyl group optionally substituted by Z, —P(═O)T2T3, or —P(═S)T2T3.
[7] Ethylene derivatives of the above-mentioned [3], in which E is a heterocyclic group optionally substituted by a C1-C4 alkyl or C1-C4 haloalkyl group—(said heterocyclic group being a 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl or 1,3,4-oxadiazol-2-yl group)—or is a halogen atom, a C2-C4 alkynyl group, a phenylethynyl group optionally substituted by a Z, a C1-C4 haloalkyl group, CN, NO2, N3, CHO, a C2-C5 alkylcarbonyl group, a C2-C5 alkoxycarbonyl group, a C2-C4 alkylaminocarbonyl group, a C3-C9 dialkylaminocarbonyl group, a benzoyl group optionally substituted by Z, an aminothiocarbonyl group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a phenylsulfenyl group optionally substituted by Z, a phenylsulfinyl group optionally substituted by Z, a phenylsulfonyl group optionally substituted by Z, —P(═O)T2T3, or —P(═S)T2T3.
(8] Ethylene derivatives of the above-mentioned [4], in which Q is a phenyl group optionally substituted by G, an oxazolyl group optionally substituted by R, a thiazolyl group optionally substituted by R, a pyrazolyl group optionally substituted by R, a 1,2,3-triazolyl group optionally substituted by R, a pyridinyl group optionally substituted by R, or a pyrimidinyl group optionally substituted by R.
[9] Ethylene derviatives of the above-mentioned [8], in which Q is a phenyl group optionally substituted by G.
[10] Ethylene derivatives of the above-mentioned [8], in which Q is an oxazolyl group optionally subsituted by R or a 1,2,3-triazolyl group optionally substituted by R.
[11] Ethylene derivatives of the above-mentioned [8], in which Q is a thiazolyl group optionally substituted by R.
[12] Ethylene derivatives of the above-mentioned (8], in which Q is a pyrazolyl group optionally substituted by R.
[13] Ethylene derivatives of the above-mentioned 5], in which Q is a phenyl group optionally substituted by G, or is Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-25, Q-26, Q-27, Q-28, Q-29, Q-30, Q-44, Q-45, Q-46, Q-47, Q-52, Q-53, Q-54, Q-55, Q-56, or Q-57.
[14] Ethylene derivatives of the above-mentioned [7], in which Q is a phenyl group optionally subsituted by G, or is Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-25, Q-26, Q-27, Q-28, Q-29, Q-30, Q-44, Q-45, Q-46, Q-47, Q-52, Q-53, Q-54, Q-55, Q-56, or Q-57.
[15] Ethylene derivatives of the above-mentioned [13), in which Q-10, Q-44, Q-45, Q-46 or Q-47.
[16] Ethylene derivatives of the above-mentioned [13], in which Q is Q-12, Q-13 or Q-14.
[17 ] Ethylene derivatives of the above-mentioned [13], in which 0 is Q-25, Q-26, Q-27, Q-28, Q-29 or Q-30.
[18 ] Ethylene derivatives of the above-mentioned [13], in which Q is a phenyl group optionally substituted by G.
[19] Ethylene derivaties of the above-mentioned 2], in which A is a phenyl group optionally substituted by W, a thiazolyl group optionally substituted by Y, a pyrazolyl group optionally substituted by Y, a pyridinyl group optionally subsituted by Y, or a pyrimidinyl group optionally substituted by Y.
[20] Ethylene derivatives of the above-mentioned [3], in which;
Q is a phenyl group optionally subsitited by G, a naphthyl group, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-44, Q-45, Q-46, Q-49,
Figure USRE038188-20030715-C00016
A is
Figure USRE038188-20030715-C00017
Y2 is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 akoxy group, NO2, CN, or a C2-C5 alkoxycarbonyl group; and
Y3 is a halogen atom, a C1-C4 alkyl group, a C1-C6 haloalkyl group, a C2-C4 alkoxyalkyl group, or a phenyl group optionally substituted by X.
[21] Ethylene derivatives of the above-mentioned [20], in which E is CN.
[22] Ethylene derivatives of the above-mentioned [20], in which E is a heterocyclic group optionally substituted by a C1-C4 alkyl or C1-C4 haloalkyl group—(said heterocyclic group being a 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadialol-3-yl, 1,2,4-thiadiazol-3-yl or 1,3,4-oxadiazol-2-yl group)—or is a halogen atom, a C2-C4 alkynyl group, a phenylethynyl group optionally substituted by Z, a C1-C4 haloalkyl group, CN, NO2, N3, CHO, a C2-C5 alkylcarbonyl group, a C2-C5 alkoxycarbonyl group, a C2-C4 alkylaminocarbonyl group, a C3-C9 dialkylaminocarbonyl group, a benzoyl group optionally substituted by Z, an aminothiocarbonyl group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsufinyl group, a C1-C4 alkylsulfonyl group, a phenylsulfenyl group optionally substituted by Z, a phenylsulfinyl group optionally substituded by Z, a phenylsulfonyl group optionally substituted by Z, —P(═O)T2T3, or —P(═S)T2T3.
[23] Ethylene derivatives of the above-mentioned [1], which are selected from the following:
Figure USRE038188-20030715-C00018
Figure USRE038188-20030715-C00019
Figure USRE038188-20030715-C00020
Figure USRE038188-20030715-C00021
Figure USRE038188-20030715-C00022
Figure USRE038188-20030715-C00023
[24] An agricultural chemical comprising, as the active ingredient, one or more ethylene derivatives of the above-mentioned [1] to [23].
[25] An agent for preventing the attachment of aquatic organisms containing, as an active ingredient, one or more ethylene derivatives of the above-mentioned [1] to [23].
MODES OF CARRYING OUT THE INVENTION
The moiety —C(E)═C(OB)— of the compounds (I) of the present invention includes two isomers of E-form and Z-form, both of which are within the scope of the invention.
It will be understood that the compounds (I) of the present invention where the substituent B is a hydrogen atom exist as tautomers to be represented by the following:
Figure USRE038188-20030715-C00024
Although the compounds (I) will exist essentially as the enol-form (1′), they could be as the tautomer form (2) under some conditions. It should be understood that the present invention includes all these three tautomers and their mixtures.
Now, preferred embodiments of Q, A, B, E, G, R, R1, Y, Y1, Y2, W, X, Z, T1, T2, T3, T4, T5, T6, T7, T8, U1, U2, m, n, p and q are referred to hereinunder.
The heterocyclic group for Q, A and B indicates the following meanings.
Specifically, thienyl is thiophen-2-yl or thiophen-3-yl; furyl is furan-2-yl or furan-3-yl; pyrrolyl is pyrrol-1-yl, pyrrrol-2-yl or pyrrol-3-yl; oxazolyl is oxazol-2-yl, oxazol-3-yl, oxazol-4-yl or oxazol-5-yl; thiazolyl is thiazol-2-yl, thiazol-4-yl or thiazol-5-yl; imidazolyl is imidazol-1-yl, imidazol-2-yl or imidazol-4-yl; isoxazolyl is isoxazol-3-yl, isoxazol-4-yl or isoxazol-5-yl; isothiazolyl is isothiazol-3-yl, isothiazol-4-yl or isothiazol-5-yl; pyrazolyl is pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl or pyrazol-5-yl; 1,3,4-oxadiazolyl is 1,3,4-oxadiazol-2-yl; 1,3,4-thiadiazolyl is 1, 4-thiadiazol-2-yl; 1,2,4-oxadiazolyl is 1,2,4-oxadiazol-3-yl or 1,2,4-oxadiazol-5-yl; 1,2,4-thiadizolyl is 1,2,4-thiadiazol-3-yl or 1,2,4-thiadiazol-5-yl; 1,2,4-traizolyl is 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl or 1,2,4-triazol-4-yl; 1,2,3-thiadiazolyl is 1,2,3-thiadiazol-4-yl or 1,2,3-thiadiazol-5-yl; 1,2,3-triazolyl is 1,2,3-triazol-1-yl; 1,2,3-triazol-2-yl or 1,2,3-triazol-4-yl; 1,2,3,4-tetrazolyl is 1,2,3, 4-tetrazol-1-yl, 1,2,3,4-tetrazol-2yl or 1,2,3,4-tetrazol-5-yl; pyridinyl is pyridin-2yl, pyridin-3-yl or pyridin-4-yl; pyrimidinyl is pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl; pyrazinyl is pyrazin-2-yl; pyridazinyl is pyridazin-3-yl or pyridazin-4-yl; 1,3,5-triazinyl is 1,3,5-triazin-2-yl; 1,2,4-triazinyl is 1,2,4-triazin-3-yl, 1,2,4-triazin5-yl or 1,2,4-triazin-6-yl; 1,2,4,5-tetrazinyl is 1,2,4,5-tetrazin-3-yl; pyrazolinyl is 3-pyrazolin-1-yl, 3-pyrazolin-3-yl, 3-pyrazolin-4-yl or 3-pyrazolin-5-yl; imidazolinyl is 1-imidazolin-3-yl, 1-imidazolin-2yl, 1-imidazolin-4-yl or 4-imidazolin-2-yl; oxazolinyl is 2-oxazolin-2-yl, 2-oxazolin-4-yl or 2-oxazolin-5-yl; isoxazolinyl is 2-isoxazolin-3-yl, 2-isoxazolin-4-yl or 2-isoxazolin-5-yl; thiazolinyl is 2-thiazolin-2-yl, 2-thiazolin-4-yl or 3-thiazolin-2-yl; imidazolidinon-yl is imidazolidin-2-on-1-yl; imidazolinon-yl is 2-imidazolinon-1-yl; and 3(2H)-pyridazinon-yl is 3(2H)-pyridazinon-2-yl, 3(2H)-pyridazinon-4-yl, 3(2H)-pyridazinon-5-yl or 3(2H)-pyridazinon-6-yl.
Preferred scope of Q is the following groups.
QI: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl.
QII: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, , 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl.
QIII: phenyl, thienyl, oxazolyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, 1,2,3-triazolyl.
QIV: phenyl.
QV: oxazoly.
QVI: thiazolyl.
QVII: pyrazolyl.
QVIII: pyrimidinyl.
QIX: 1,2,3-triazolyl.
Preferred scope of A is the following groups.
AI: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl.
AII: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,3-thiadiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl.
AIII: phenyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidinyl.
AIV: thiazolyl, pyrazolyl, pyridinyl.
AV: thiazolyl.
AVI: pyrazolyl.
AVII: pyridinyl.
Preferred scope of B is the following groups.
BI: H, C2-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkoxyalkyl, CH3OC2 H4 OCH2, C1-C4 alkylsulfonyl, phenylsulfonyl optionally substituted by halogen or C1-C4 alkyl, —SO2CF3, C2-C8 dialkylaminosulfonyl, C3-C9 dialkylaminothiocarbonyl, C3-C9 alkoxycarbonylalkyl, —C(═O)T1, —P(═O)T2T3, —P(═S)T2T3, alkali metal, alkaline earth metal or NHT4T5T6.
BII: H, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkoxyalkyl, CH3OC2 H4 OCH2, C1-C4 alkylsulfonyl, —SO2CF3, —C(═O)T1, alkali metal, alkaline earth metal or NHT4T5T6.
BIII: H, C2-C4 alkoxyalkyl, C1-C4 alkylsulfonyl, —SO2CF3, —C(═O)T1, alkali metal, alkaline earth metal, NHT4T5T6.
BIV: C2-C4 alkoxyalkyl, C1-C4 alkylsulfonyl, —SO2CF3, —C(═O)T1, alkali metal, alkaline earth metal or NHT4T5T6.
Preferred scope of E is the following grouips.
EI: halogen, C2-C4 alkynyl, phenylethynyl optionally substituted by Z, C1-C4 haloalkyl, CN, NO2, N3, CHO, C2-C5 alkylcarbonyl, C2-C5 alkoxycarbonyl, C2-C4 alkylaminocarbonyl, C3-C9 dialkylaminocarbonyl, benzoyl optionally substituted by Z, aminothiocarbonyl, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, phenylsulfenyl optionally substituted by Z, phenylsulfinyl optionally substituted by Z, phenylsulfonyl optionally substituted by Z, —P(═O)T2T3, —P(═S)T2T3.
EII: halogen, C2-C4 alkynyl, phenylethynyl optionally substituted by Z, CN, C2-C5 alkylcarbonyl, C2-C5 alkoxycarbonyl, C2-C4 alkylaminocarbonyl, C3-C9 dialkylaminocarbonyl, benzoyl optionally substituted by Z, aminothiocarbonyl, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, phenylsulfenyl optionally substituted by Z, phenylsulfinyl optionally substituted by Z, phenylsulfonyl optionally substituted by Z or —P(═O)T2T3.
EIII: CN.
Preferred scope of G is the following groups.
GI: substituents freely selected from halogen, C1-C6 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl optionally substituted by C1-C3 alkyl, C1-C6 alkoxy, C2-C4alkenyloxy, C2-C4 alkynyloxy, C1-C4 haloalkoxy, C2-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C4 alkenylsulfenyl, C2-C4 alkenylsulfinyl, C2-C4 alkenylsulfonyl, C2-C4 alkylnylsulfenyl, C2-C4 alkynylsulfinyl, C2-C4 alkynylsulfonyl, C1-C4 haloalkylsulfenyl, C2-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C2-C4 haloalkenylsulfenyl, C2-C4 haloalkenylsulfinyl, C2-C4 haloalkenylsulfonyl, C2-C4 haloalkynylsulfenyl, C2-C4 haloalkynylsulfinyl, C2-C4 haloalkynylsulfonyl, NO2, CN, —NU1U2, methoxy substituted by phenyl optionally substituted by halogen, or C1-C4 alkyl, C2-C6 alkoxycarbonyl, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C4 alkylcarbonyloxy, C2-C6 haloalkylcarbonyloxy, C3-C7 dialkylaminocarbonyloxy, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, benzoyl optionally substituted by Z, pyridyl optionally substituted by Z, and pyridyloxy optionally substituted by Z (provided that when the substituent is two or more, said substituents may be the same or different) and the number of the substituent G, is 1, 2, 3 or 4, or G is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring
GII: substituents freely selected from halogen, C1-C6 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C6 cycloalkyl optionally substituted by C1-C3 alkyl, C1-C6 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 haloalkoxy, C2-C4 haloalkenyloxy, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C4 alkenylsulfenyl, C2-C4 alkenylsulfinyl, C2-C4 alkenylsulfonyl, C2-C4 alkynylsulfenyl, C2-C4 alkynylsulfinyl, C2-C4 alkynylsulfonyl, C1-C4 haloalkylsulfenyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C2-C4 haloalkenylsulfenyl, C2-C4 haloalkenylsulfinyl, C2-C4 haloalkenylsulfonyl, methoxy substituted by phenyl optionally substituted by halogen or C1-C4 alkyl, C2-C6 alkoxycarbonyl, C2-C5 alkylcarbonyloxy, C2-C5 haloalkylcarbonyloxy, phenoxy optionally substituted by Z, and pyridyloxy optionally substituted by Z (provided that the number of the substituent is two or more, said substituebts may be the same or different), and the number of the substituent, G, is 1, 2 or 3.
GIII: substituents freely selected from halogen C1-C6 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl optionally substituted by C1-C3 alkyl, C1-C6 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 haloalkoxy, C2-C4 haloalkenyloxy, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C4 alkenylsulfenyl, C2-C4 alkenylsulfinyl, C2-C4 alkenylsufonyl, C2-C4 alkynylsulfenyl, C2-C4 alkynylsulfinyl, C2-C4 alkynylsulfonyl, C1-C4 haloalkylsulfenyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C2-C4 haloalkenylsulfenyl, C2-C4 haloalkenylsulfinyl, C2-C4 haloalkenylsulfonyl, methoxy substituted by phenyl optionally substituted by halogen or C1-C4 alkyl, C2-C6 alkoxycarbonyl, C2-C5 alkylcarbonyloxy, phenoxy optionally substituted by Z, and pyridyloxy optionally substituted by Z (provided that when the substituent is two or more, said substituents may be the same or different), and the number of the substituent, G is 1 or 2.
Preferred scope of R is the following group.
RI: substituents freely selected from halogen, C1-C6 alkyl, C1-C3 alkyl substituted by phenyl optionally substituted by halogen or C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl optionally substituted by C1-C3 alkyl, C1-C4 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 haloalkoxy, C2-C4 haloalkenyloxy, C2-C4 haloalkynyloxy, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C4 alkenylsulfenyl, C2-C4 alkenylsulfinyl, C2-C4 alkenylsulfonyl, C2-C4 alkynylsulfenyl, C2-C4 alkynylsulfinyl, C2-C4 alkynylsulfonyl, C1-C4 haloalkylsulfenyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C2-C4 haloalkenylsulfenyl, C2-C4 haloalkenylsulfinyl, C2-C4 haloalkenylsulfonyl, NO2, CN, —NU1U2, naphthyl, C2-C4 alkoxycarbonyl, C2-C4 alkoxyalkyl, phenyl optionally substituted by X, pyridyl optionally substituted by X, and thienyl optionally substituted by X (provided that when the substituent is two or more, said substituents may be the same or different), and the number of the substituent, R, is 1, 2 or 3, or R is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring.
RII: substituents freely selected from halogen, C1-C6 alkyl, C1-C3 alkyl substituted by phenyl optionally substituted by halogen or C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl optionally substituted by C1-C3 alkyl, NO2, CN, —NU1U2, naphthyl, C2-C4 alkoxycarbonyl, C1-C4 alkoxyalkyl, phenyl optionally substituted by X, and pyridyl optionally substituted by X (provided that when the substituents is two or more, said substituents may be the same or different), and the number of the substituents, R, is 1, 2 or 3.
RIII: substituents freely selected from halogen, C1-C6 alkyl, C1-C3 alkyl substituted by phenyl optionally substituted by halogen or C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl optionally substituted by C1-C3 alkyl, NO2, CN, —NU1U2, naphthyl, C2-C4 alkoxycarbonyl, phenyl optionally substituted by X, and pyridyl optionally substituted by X (provided that when the substituent is two or more, said substituents may be the same or different), and the number of the substituent R, is 1 or 2.
Depending on the type of the heterocyclic group to be substituted by R, the number of R differs. For the group of 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl or 1,2,3,4-tetrazolyl, the number of R is 0 or 1, preferably 1. For the group of thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl or 1,2,4-triazinyl, the number of R is an integer of from 0 to 2, preferably 1 or 2. For the group of thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of R is an integer of from 0 to 3, preferably an integer of from 0 to 2, member preferably 1 or 2. For the group of pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of R is an integer of from 0 to 4, preferably an integer of from 0 to 3, more preferably 1 or 2.
Preferred scope of Y is the following groups.
YI: substituents freely selected from halogen, C1-C6 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 haloalkoxy, C2-C4 haloalkenyloxy, C2-C4 haloalkynyloxy, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C4 alkenylsulfenyl, C2-C4 alkenylsulfinyl, C2-C4 alkenylsulfonyl, C2-C4 alkynylsulfenyl, C2-C4 alkynylsulfinyl, C2-C4 alkynylsulfonyl, C1-C4 haloalkylsulfenyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C2-C4 haloalkenylsulfenyl, C2-C4 haloalkenylsulfinyl, C2-C4 haloalkenylsulfonyl, C2-C4 haloalkynylsulfenyl, C2-C4 haloalkynylsulfinyl, C2-C4 haloalkynylsulfonyl, NO2, CN, —NU1U2, C2-C4 alkoxycarbonyl, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyloxy, C2-C4 haloalkylcarbonyloxy, and phenyl optionally substituted by X (provided that the substituent is two or more, said substituents may be the same or different) and the number of the substituent, Y, is 1, 2 or 3.
YII: substituents freely selected from halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfenyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, NO2,CN, C2-C4 alkoxycarbonyl, and phenyl optionally substituted by X (provided that when the substituent is two or more, said substituents may be the same or different) and the number of the substituent, Y, is 1, 2 or 3.
Depending on the type of the heterocyclic group to be substituted by Y, the number of Y differs. For the group of 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-thiadiazolyl or 1,2,3,4-tetrazolyl, the number of Y is 0 or 1, preferably 1. For the group of thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl or 1,2,4-triazinyl, the number of Y is an integer of from 0 to 2, preferably 1 or 2. For the group of thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Y is an integer of from 0 to 3, preferably an integer of from 0 to 2, more preferably 1 or 2. For the group of pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of Y is an integer of from 0 to 4, preferably an integer of from 0 to 3, more preferably 1 or 2.
Preferred scope of W is the following group.
WI: substituents freely selected from halogen, C1-C6 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfenyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C2-C4 alkenylsulfenyl, C2-C4 alkenylsulfinyl, C2-C4 alkenylsulfonyl, C2-C4 haloalkenylsulfenyl, C2-C4 haloalkenylsulfinyl, c2-C4 haloalkenylsufonyl, C2-C4 alkynyloxy, C2-C4 alkynylsulfenyl, C2-C4 alkynylsulfinyl, C2-C4 alkynylsulfonyl, NO2, CN, C2-C4 alkoxycarbonyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C4 alkylcarbonyloxy, and —NU1U2 (provided that when the substituent is two or more, said substituents are the same or different) and the number of the substituent, W is 1, 2, 3 or 4.
WII: substituents freely selected from halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfenyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C2-C4 alkenylsulfenyl, C2-C4 alkenylsulfinyl, C1-C4 alkenylsulfony, C2-C4 alkynyloxy, C2-C4 alkynylsulfenyl, C2-C4 alkynylsulfinyl, C2-C4 alkynylsulfonyl, NO2, and CN (provided that the substituent is two or more, said substituents may be the same or different) and the number of the substituent, W, is 1, 2 or 3.
WIII: substituents freely selected from halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfenyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, NO2, and CN (provided that when the substituent is two or more, the substituents may be the same or different) and the number of the substituent, W, is 1 or 2.
Preferred scope of T1 is the following groups.
T1I: C1-C18 alkyl, C2-C6 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkyl substituted by phenyl optionally substituted by halogen or C1-C4 alkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl optionally substituted by C1-C3 alkyl, cycloalkyl substituted by phenyl optionally substituted by halogen or C1-C4 alkyl, C2-C4 alkenyl substituted by phenyl optionally substituted by halogen or C1-C4 alkyl, C1-C10 alkoxy, C1-C4 haloalkoxy, C2-C6 alkenyloxy, C3-C6 cycloalkoxy optionally substituted by C1-C4 alkyl, benzyloxy, C2-C6 alkoxycarbonyl, —NU1U2, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, phenylthio optionally substituted by Z, naphthyl, and heterocyclic group optionally substituted by Z. (said heterocyclic group being selected from thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, and 1,2,4-triazinyl groups).
T1II: C1-C1 alkyl, C2-C6 alkenyl, C1-C4 haloalkyl, C2-C4 alkoxyalkyl, C1-C4 alkyl substituted by phenyl optionally substituted by halogen or C1-C4 alkyl, C3-C6 cycloalkyl optionally substituted by C1-C3 alkyl, cycloalkyl substituted by phenyl optionally substituted by halogen or C1-C4 alkyl, C2-C4 alkenyl substituted by phenyl optionally substituted by halogen or C1-C4 alkyl, C1-C10 alkoxy, C1-C4 haloalkoxy, C2-C5 alkenyloxy, C3-C6 cycloalkoxy, benzyloxy, C2-C5 alkoxycarbonyl, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, phenylthio, naphthyl, and heterocyclic group optionally substituted by Z (said heterocyclic group selected from thienyl, furyl, oxazolyl, thiazolyl, pyrazolyl and pyridinyl groups).
T1III: C1-C17 alkyl, C2-C6 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxyalkyl, C1-C4 alkyl substituted by phenyl, C3 -C6 cycloalkyl optionally substituted C1-C3 alkyl, cycloalkyl substituted by phenyl, C2-C4 alkenyl substituted by phenyl, C1-C8 alkoxy, C1-C4 haloalkoxy, C2-C5 alkenyloxy, C3-C6 cycloalkoxy, benzyloxy, C1-C5 alkoxycarbonyl, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, phenylthio, naphthyl, pyrazolyl optionally substituted by Z or pyridinyl optionally substituted by Z.
Preferred scope of T2 is the following groups.
T2I: phenyl, C1-C4 alkyl, C1-C4 alkoxy of C1-C4 alkylsulfenyl.
Preferred scope of T4 is the following groups.
T3I: phenyl, C1-C4 alkyl, C3-C6 alkoxy or C1-C4 alkylsulfenyl.
Preferred scope of T4 is the following groups.
T4I: H, C1-C4 alkyl, C3-C6 cycloalkyl or benzyl. Also preferred is such that any two of T4, T5 and T6, together with the nitrogen atom to which they are bonded, forms a 5-, 6- or 7-membered ring optionally having oxygen, nitrogen and/or sulfur atoms.
Preferred scope of T5 is the following groups.
T5I: H, C1-C4 alkyl, C3-C6 cycloalkyl or benzyl. Also, preferred is such that any two of T4, T5 and T6, together with the nitrogen atom to which they are bonded, forms a 5-, 6- or 7-membered ring optionally having oxygen, nitrogen and/or sulfur atoms.
Preferred scope of TO is the following groups.
T6I: H, C1-C4 alkyl, C3-C6 cycloalkyl or benzyl. Also, preferred is such that any two of T4, T5 and T6, together with the nitrogen atom to which they are bonded, forms a 5-, 6- or 7-membered ring optionally having oxygen, nitrogen and/or sulfur atoms.
Preferred scope of X is the following groups.
XI: substituents freely selected from halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C5 alkenylsulfenyl, C2-C5 alkenylsulfinyl, C2-C5 alkenylsulfonyl, C1-C4 haloalkylsulfenyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, NO2, CN, —NU1U2 and C2-C5 alkoxycarbonyl (provided that the substituent is two or more, said substituents may be the same or different) and the substituent X is 1,2 or 3.
XII: substituents freely selected from halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C5 alkenylsulfenyl, C1-C4 haloalkylsulfenyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, and NO2 (provided that when the substituent is two or more, said substituents may be the same or (different) and the number of the substituent X, is 1, 2 or 3.
XIII: substituents freely selected from halogen, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy (provided that when the substituent is two is more, said substituents may be the same or different) and the number of the substituent, X, is 1 or 2.
Depending on the type of the ring to be substituted by X, the number of X differs. For phenyl, the number of X is an integer of from 0 to 5, preferably an integer of from 0 to 3, more preferably an integer of from 0 to 2. For pyridyl, the number of X is an integer of from 0 to 4, preferably 0, 1 or 2, more preferably 0 or 1. For thienyl, the number of X is an integer of from 0 to 3, preferably 0 or 1.
Preferred scope of Z is the following groups.
ZI: substituents freely selected from halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C 4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C5 alkenylsulfenyl, C2-C6 alkenylsulfinyl, C2-C, alkenylsulfonyl, C1-C4 haloalkylsulfenyl, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, NO2, CN, —NU1U2 and C2-C5 alkoxycarbonyl (provided that when the substituent is two or more, said substituents may be the same or different) and the number of the substituent, Z, is 1, 2, 3, or 4.
ZII: substituents freely selected from halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylsulfenyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C5 alkenylsulfenyl, C2-C5 alkenylsulfinyl, C2-C5 alkenylsulfonyl, C1-C4 haloalkylsulfenyl, C1-C4 haloalkylsulfinyl and C1-C4 haloalkylsulfonyl (provided that when the substitutent is two or more, said substituents may be the same or different) and the substituent Z, is 1, 2, 3, or 4.
Depending on the type of the ring to be substituted by Z, the number of Z differs. For phenyl, the number of Z is an integer of from 0 to 5, preferably an integer of from 0 to 4, more preferably 0, 1, 2 or 3, even more preferably 0, 1 or 2. For naphthyl, the number of Z is an integer of from 0 to 7, preferably 0. Where the ring to be substituted by Z is a heterocyclic group, the number of the substituents of Z also differs depending on the type of the heterocyclic group. For the group of 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,3,4-tetrazolyl or 1,2,3,5-tetrazolyl, the number of Z is 0 or 1. For the group of thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl or 1,2,4-triazinyl, the number of Z is an integer of from 0 to 2, preferably 1 or 2. For the group of thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Z is an integer of from 0 to 3, preferably an integer of from 0 to 2, more preferably 1 or 2. For the group of pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of Z is an integer of from 0 to 4, preferably an integer of from 0 to 2, more preferably 1 or 2.
Preferred scope of T7 is the following groups.
T7I: H, phenyl, benyzl or C1-C4 alkyl. Also preferred is such that T7 and T8, together with the carbon atom to which they are bonded, form a 5-membered or 6-membered ring.
Preferred scope of T8 is the following groups.
T8I: phenyl, benzyl or C1-C4 alkyl. Also preferred is such that T7 and T8, together with the carbon atom to which they are bonded, form a 5-membered or 6 -membered ring.
Preferred scope of U1 is the following groups.
U1I: H, C1-C4 alkyl or C2-C5 alkylcarbonyl. Also preferred is such that U1 and U2, together with nitrogen atom to which they are bonded, form a 5-, 6- or 7-membered ring.
Preferred scope of U2 is the following groups.
U2I: H, C1-C4 alkyl or C2-C5 alkylcarbonyl. Also preferred is such that U1 and U2, together with the carbon atom to which they are bonded, form a 5-, 6- or 7-membered ring.
Preferably, m is 1, 2, or 3, more preferably 1 or 2.
Preferably n is 0, 1, 2 or 3, more preferably 1 or 2.
Preferably, p is 1 or 2.
The above-mentioned preferred groups in the scopes of the preferred substituents can be optionally combined and show the scopes of the preferred compounds of the present invention. Hereinunder mentioned are especially preferred scopes.
Compounds of the invention comprising preferred substituents of QI, AI, BI, EI, GI, RI, YI, WI, T1I, T2I, T2I T3I, T4I, T5I, T6I, XI, ZI, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QI, AI, BI, EIII, GI, RI, YI, WI, T1I, T2I, T3I, T4I, T5I, T6I, XI, ZI, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QII, AII, BI, EII, GI, RI, YI, WI, T1I, T2I, T3I, T4I, T5I, T6I, XI, ZI, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QII, AII, BI, EIII, GI, RI, YI, WI, T1I, T2I, T3I, T4I, T5I, T6I, XI, ZI, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QIII, AIII, BI, EIII, GI, RI, YI, WI, T1I, T2I, T3I, T4I, T5I, T6, XI, ZI, T7I, T8, U1I and U2I.
Compounds of the invention comprising preferred substituents of QIII, AIII, BII, EIII, GII, RII, YII, WII, T1II, T2I, T3I, T4I, T5I, T6I, XII, ZII, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QIII, AIII, BII, EIII, GIII, RIII, YII, WII, T1III, T2I, T3I, T4I, T5I, T6I, XIII, ZII, T7I, T8I, U1I and U1I.
Compounds of the invention comprising preferred substituents of QIII, AIV, BIII, EIII, GIII, RIII, YII, WII, T1III, T2I, T3I, T4I, T5I, T6I, XIII, ZII, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QIV, AIV, BIII, EIII, GIII, RIII, YII, WII, T1III, T2I, T3I, T4I, T5I, T6I, XIII, ZII, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QV, AIII, BIII, EIII, GIII, RIII, YII, WII, T1III, T2I, T3I, T4I, T5I, T6I, XIII, ZII, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QVI, AIII, BIII, EIII, GIII, RIII, YII, WII, T1III, T2I, T3I, T4I, T5I, T6I, XIII, ZII, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QVI, AIV, BIII, EIII, GIII, RIII, YII, WII, T1III, T2I, T3I, T4I, T5I, T6I, XIII, ZII, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QVII, AIII, BIII, EIII, GIII, RIII, YII, WII, T1III, T2I, T3I, T4I, T5I, T6I, XIII, ZII, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QVIII, AIII, Bill, EIII, GIII, RIII, YII, WII, T1III, T2I, T3I, T4I, T5I, T6I, XIII, ZII, T7I, T8I, U1I U2.
Compounds of the invention comprising preferred substituents of QIX, AIII, Bill, EIII, GIII, RIII, YII, WII, T1III, T2I, T3I, T4I, T5I , T6I, XIII, ZII, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QIII, AV, BIII, EIII, GIII, RIII, YII, WII, T1III, T2I, T3I, T4I, T5I, T6I, XIII, ZII, T7I, T8I, U1I and U2I.
Compounds of the invention comprising preferred substituents of QIII, AVI, BIII, EIII, GIII, RIII, YII, WII, T1III, T2I, T3I, T4I, T5I, XIII, ZII, T7I, T8I , U1I and U2I.
Compounds of the invention comprising preferred substituents of QIII, AVII, BIII, EIII, GIII, RIII, YII, WII, T1III, T2I, T3I, T4I, T5I, T6I, XIII, ZII, T7I, T8I, U1I and U2I.
Now specific examples of Q, A, B, E, G, R, R1, Y, Y1, Y2, W, X, Z, T1, T2, T3, T4, T5, T6, T7, T8, U1 and U2 are mentioned below.
The halogen atom for E, G, R, R1, W, X, Y, Y1, Y2, Y3 and Z includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Preferred are a fluorine atom, a chlorine atom and a bromine atom.
The alkyl group for B, G, R, R1, T1, T2, T3, T4, T5, T6, T7, T8, U1, U2, W, X, Y, Y1, Y2, Y3 and Z may be a straight chain or branched alkyl group having indicated carbon atoms, which includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, pentyl-1, pentyl-2, pentyl-3, 2-methylbutyl-1, 2-methylbutyl-2, 2-methylbutyl-3, 3-methylbutyl-1, 2,2-dimethylpropyl-1, hexyl-1, hexyl-2, hexyl-3, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n-heptyl, n-octyl, n-nonyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl and n-eicosyl groups.
The alkenyl group for G, R, R1, T1, T4, T5, T6, Y1 and W may be a straight chain or branched alkenyl group having indicated carbon atoms, which includes, for example, ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl and 1-ethyl-1-methyl-2-propenyl groups.
The alkynyl group for E, G, R, R1, Y1 and W may be a straight chain or branched alkynyl group having indicated carbon atoms, which includes, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, hexynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl ,1a-dimethyl-2-butynyl, 1 1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl and 2-ethyl-3-butynyl groups.
The haloalkyl group for B, E, G, R, R1, T1, W, X, Y, Y1, Y2, Y3 and Z may be a straight chain or branched haloalkyl group having indicated carbon atoms, which includes, for example, fluoromethyl, chloromethyl, bromomethyl, fluoroethyl, chloroethyl, bromoethyl, fluoro-n-propyl, chloro-n-propyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethl, difluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluoroethyl, hexafluoro-n-propyl, chlorobutyl, fluorobutyl, chloro-n-pentyl, fluoro-n-pentyl, chloro-n-hexyl and fluoro-n-hexyl groups.
The C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group for G, R, T1, T4, T5 and T6 includes, for example, cyclopropyl, 1-methylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, 1-ethylcyclobutyl, 1-n-butylcyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 1-methylcyclohexyl and 4-methylcyclohexyl groups.
The C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen atom or a C1-C4 alkyl group for B, G, R and T1 includes, for example, benzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-tert-butylbenzyl, 1-phenylethyl, 1-(3-chlorophenyl)ethyl, 2-phenylethyl, 1-methyl-1-phenylethyl, 1-(4-chlorophenyl)-1-methylethyl, 1-(3-chlorophenyl)-1-methylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 1-phenylpropyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl, 1-methyl-1-phenylpropyl, 1-methyl-2-phenylpropyl, 1-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl, 2-(4-chlorophenyl)-2-methylpropyl and 2-methyl-2-(3-methylphenyl)propyl groups.
For T1, the C3-C6 cycloalkyl group substituted by a phenyl group optionally substituted by a halogen atom or a C1-C4 alkyl group includes, for example, 1-phenylcyclopropyl, 1-(3-chlorophenyl)cyclopropyl, 1-(4-chlorophenyl)cyclopropyl, 1-(4-bromophenyl)cyclopropyl, 1-(4-fluorophenyl)cyclopropyl, 1-(4-ethylphenyl) cyclopropyl, 1-(4-propylphenyl)cyclopropyl, 2-phenylcyclopropyl, 1-phenylcyclobutyl, 2-phenylcyclobutyl, 1-phenylcyclopentyl, 1-(4-chlorophenyl)cycloptentyl, 2-phenylcyclopentyl, 3-phenylcyclopentyl, 1-phenylcyclohexyl, 1-(3-fluorophenyl)cyclohexyl, 1-(4-chlorophenyl)cyclohexyl, 1-(4-tert-butylphenl)cyclohexyl, 2-phenylcyclohexyl, 3-phenylcyclohexyl and 4-phenylcyclohexyl groups.
For T1, the cyclopropyl group substituted by both a phenyl group optionally substituted by a halogen atom or a C1-C4 alkyl group and a C1-C4 alkyl group includes, for example, 2,2-dimethyl-1-phenylcyclopropyl, 1-(4-chlorophenyl)-2,2-dimethylcyclopropyl, 2,2-dimethyl-3-phenylcyclopropyl, 3-(3-chrlorophenyl)-2,2-dimethylcyclopropyl, (4-chlorophenyl)-2,2-dimethyl-3-phenylcyclopropyl, (4-bromophenyl)-2,2-dimethyl-3-phenylcyclopropyl, 2,2-dimethyl-3-(4-methylphenyl) cyclopropyl and (4-tert-butylphenyl)-2,2-dimethyl-3-phenylcyclopropyl groups.
For T1, the C3-C4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen atom or a C1-C4 alkoxy group and a halogen atom includes, for example, 2,2-dichloro-1-phenylcyclopropyl, 2,2-dichloro-1-(3-chlorophenyl)cyclopropyl, 2,2-dichloro-1-(4-methoxyphenyl)cyclopropyl, 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropyl, 2,2-dichloro-(4-i-propyloxyphenyl)cyclopropyl, 2,2-dichloro-(4-t-butylphenyl)cyclopropyl, 2,2-dichloro-1-(4-methoxyphenyl)-3-phenylcyclopropyl and 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorobutyl groups.
For T1, the cyclopropyl group substituted by both a C2-C4 alkenyl group optionally substituted by a halogen atom, and a C1-C4 alkyl group includes, for example, 2,2-dimethyl-3-(2,2-dimethylethenyl)cyclopropyl, 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropyl, 3-(2,2-dichloroethyenyl)-2,2-dimethylcyclopropyl and 3-(2,2-chlorotrifluoroethenyl)-2,2-dimethylcyclopropyl groups.
For T1, the C3-C6 cycloalkoxy group optionally substituted by a C1-C3 alkyl group includes, for example, cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy and 1-methylcyclopropoxy groups.
For T1, the C2-C4 alkenyl group substituted by a phenyl group optionally substituted by a halogen atom or a C1-C4 alkyl group includes, for example, 1-phenylethenyl, 2-phenylethenyl, 2-(2-chlorophenyl)ethenyl, 2-(3-chlorophenyl)ethenyl, 2-(4-chlorophenyl)ethenyl, 2-(4-methylphenyl)ethenyl, 2-(2,6-difluorophenyl)ethenyl, 2-(2,5-dimethylphenyl)ethenyl, 1-methyl-2-phenylethenyl, 2-phenyl-1-propenyl, 2-(4-bromophenyl)-1-propenyl and 2-(2,4,6-trimethylphenyl)-1-propenyl groups.
The alkoxy group for G, R, T1, T2, T3, R1, W, X, Y, Y1, Y2 and Z may be straight chain or branched alkoxy group having indicated carbon atoms, which includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1-ethyl-1-methylpropyloxy, 1-ethyl-2-methylpropyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy and n-decyloxy groups.
The C3-C6 halocycloalkyl group for G, R and T1 includes, for example, fluorocyclopropyl, difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, chlorocyclobutyl, dichlorocyclobutyl, chlorocyclopentyl, dichlorocyclopentyl, chlorocyclohexyl, dichlorocyclohexyl and tetrafluorocyclobutyl groups.
The group —NU1U2 for G, R, R1, T1, W, X, Y, Y1 and Z includes, for example, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, tert-butylamino, n-pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, n-hexylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, -1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino, 1-ethyl-2-methylpropylamino, dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino, di-sec-butylamino, diisobutylamino, di-n-pentylamino, di-n-hexylamino, methylethylamino, methylpropylamino, methylisopropylamino, methylbutylamino, methyl-sec-butylamino, methylisobutylamino, methyl-tert-butylamino, methylpentylamino, methylhexylamino, ethylpropylamino, ethylisopropylamino, ethylbutylamino, ethyl-sec-butylamino, ethyl-isobutylamino, ethylpentylamino, ethylhexylamino, phenylamino, benzylamino, N-merthylacetamido, N-ethylacetamido, N-phenylacetamido and N-acerylacetamido groups, to which is applied the indicated scope of the carbon atoms constituting it.
The C2-C5 alkoxycarbonyl group for E, G, R, R1T1, W, X, Y, Y1, Y2 and Z includes, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, iso-butoxycarbonyl and tart-butoxycarbonyl groups.
The C1-C4 haloalkoxy group for G, R, T1, W, X, Y and Z may be a straight chain or branched C1-C4 haloalkoxy group, including, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, fluorcethoxy, chlorcethoxy, bromcethoxy, difluoroethozy, trifluoroethoxy, tetrafluoroethoxy, pentafluorcethoxy, trichloroethoxy, trifluorochlorethoxy, fluoropropoxy, chloropropoxy, bromopropoxy, fluorobutoxy, chlorobutoxy, fluoro-iso-propoxy and chloro-iso-propoxy groups.
The C1-C4 alkylsulfenyl group for E, G, R, T2, T3, W, X, Y and Z includes, for example, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec-butylthio and tert-butylthio groups.
The C1-C4 alkylsulfinyl group for E, G, R, X, W, Y and Z includes, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl, iso-butylsulfinyl, sec-butylsulfinyl and tart-butylsulfinyl groups.
The C1-C4 alkylsulfonyl group for B, E, G, R, W, X, Y and Z includes, for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl, n-butylsulfonyl, iso-butylsulfonyl, sec-butylsulfonyl and tart-butylsulfonyl groups.
The C2-C4 alkoxyalkyl group for B, G, R, R1, T1, Y, Y1 and Y2 includes, for example, C1-C3 alkoxy-methyl, C1-C2 alkoxy-ethyl, methoxyethoxymethyl and methoxypropyl groups.
The C2-C4 alkylcarbonyl group for E, G, R, R1, U1, U2, Y1, Y2 and W includes, for example, acetyl, propionyl, butanoyl and iso-butanoyl groups.
The C2-C6 haloalkylcarbonyl group for G and W includes, for example, chloroacetyl, trifluoroacetyl, 3,3,3-trifluoropropionyl and pentafluoropropionyl groups.
The C2-C5 haloalkylcarbonyloxy group for G, R and Y includes, for example, chloroacetyloxy, trifluoroacetyloxy, 3,3,3-trifluoropropionyloxy and pentafluoropropionyloxy groups.
The C3-C7 dialkylaminocarbonyloxy group for G and Y includes, for example, dimethylaminocarbonyloxy, diethylaminocarbonyloxy and di-i-propylaminocarbonyloxy groups.
The naphthyl group for R, Y, Z and T1 includes, for example, 1-naphthyl and 2-naphthyl groups.
The pyridyl group optionally substituted by Z for G and T1 includes, for example, 2-pyridyl, 3-pyridyl and 4-pyridyl groups all optionally substituted by Z. Preferred are 2-pyridyl and 3-pyridyl groups both optionally substituted by Z; and more preferred is a 2-pyridyl group optionally substituted by Z.
The pyridyloxy group optionally substituted by Z for G and T1 includes, for example, 2-pyridyloxy, 3-pyridyloxy and 4-pyridyloxy groups all optionally substituted by Z.
The pyridyl group optionally substituted by X for R and R1 includes, for example, 2-pyridyl, 3-pyridyl and 4-pyridyl groups all optionally substituted by X. Preferred are 2-pyridyl and 3-pyridyl groups both optionally substituted by X; and more preferred is a 2-pyridyl group optionally substituted by X.
The pyridyloxy group optionally substituted by X for N and R1 includes, for example, 2-pyridyloxy, 3-pyridyloxy and 4-pyridyloxy groups all optionally substituted by X.
The thienyl group-optionally substituted by X for R and R1 includes, for example, 2-thienyl and 3-thienyl groups both optionally substituted by X.
The thienyl group optionally substituted by Z for G and Y1 includes, for example, 2-thienyl and 3-thienyl groups both optionally substituted by Z.
The group —N═CT7T8 for G, R, R1, Y and Y1 indicates an alkylidenamino group, a benzylidenamino group, an arylidenamino group or a cycloalkylidenamino group, including, for example, methylidenamino, ethylidenamino, propylidenamino, isopropylidenamino, 4-methyl-2-pentylidenamino, cyclopentylidenamino and cyclohexylidenamino groups.
The C2-C4 alkylaminocarbonyl group for E includes, for example, methylaminocarbonyl, ethylaminocarbonyl and n-propylaminocarbonyl groups.
The C3-C9 dialkylaminocarbonyl group for E includes, for example, dimethylaminocarbonyl, diethylaminocarbonyl, di-n-propylaminocarbonyl, di-isopropylaminocarbonyl and di-n-butylaminocarbonyl groups.
The C1-C4 alkylaminosulfonyl group for B includes, for example, methylaminosulfonyl, ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl and n-butylaminosulfonyl groups.
The C2-C8 dialkylaminosulfonyl group for B includes, for example, dimethylaminosulfonyl, diethylaminosulfonyl, di-n-propylaminosulfonyl, di-isopropylaminosulfonyl and di-n-butylaminosulfonyl groups.
The C2-C5 alkylaminothiocarbonyl group for B includes, for example, methylaminothiocarbonyl, ethylaminothiocarbonyl, n-propylaminothiocarbonyl, isopropylaminothiocarbonyl and n-butylaminothiocarbonyl groups.
The C3-C9 dialkylaminothiocarbonyl group for B includes, for example, dimethylaminothiocarbonyl, diethylaminothiocarbonyl, di-n-propylaminothiocarbonyl, di-isopropylaminothiocarbonyl and di-n-butylaminothiocarbonyl groups.
The C1-C4 alkyl group substituted by a benzoyl group optionally substituted by a halogen atom or a C1-C4 alkyl group for B includes, for example, phenacyl, 2-fluorophenacyl, 3-chlorophenacyl, 4-bromophenacyl, 2-methylphenacyl,3-ethylphenacyl,4-i-propylphenacyl and 4-t-butylphenacyl groups.
The phenylsulfonyl group optionally substituted by a halogen atom or a C1-C4 alkyl group for B includes, for example, 2-fluorophenylsulfonyl, 4-fluorophenylsulfonyl, 2-chlorophenylsulfonyl, 4-chlorophenylsulfonyl, 4-bromophenylsulfonyl, 2,5-dichlorophenylsulfonyl, pentafluorophenylsulfonyl, 4-methylphenylsulfonyl, 2-methylphenylsulfonyl, 4-t-butylphenylsulfonyl, 2,5-dimethylphcnylsulfonyl, 2,4-dimethylphenylsulfonyl, 2,4,6-trimethylphenylsulfonyl and 2,4,6-tri-i-propylphenylsulfonyl groups.
The C2-C5 cyanoalkyl group for G and B includes, for example, cyanomethyl, 2-cyanoethyl, 3-cyanopropyl and 1-cyano-1-methylethyl groups.
The C3-C9 alkoxycarbonylalkyl group for B may be a straight chain or branched one, including, for example, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycerbonylmethyl, i-propoxycarbonylmethyl, n-butoxycarbonylmethyl, i-butoxycarbonylmethyl, t-butoxycarbonylmethyl, n-hexyloxycarbonylmethyl, n-heptyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-n-butoxyethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 1-methoxycarbonylpropyl, 3-ethoxycarbonylpropyl, 4-methoxycarbonylbutyl, 6-ethoxycarbonylhexyl, 1-methoxycarbonyl-1-methylethyl, 1-iso-propoxycarbonyl-1-methylethyl and 1-ethoxycarbonyl-2-methylpropyl groups.
The alkali metal for B includes, for example, lithium sodium and potassium.
The alkaline earth metal for H includes, for example, magnesium, calcium, strontium and barium. Preferred are magnesium, calcium and barium.
The ammonium group of NHT4T5T6 for B includes, for example, ammonium, monomethylammonium, dimethylammonium, trimethylammonium, diethylammonium, triethylammonium, di-isopropylammonium, di-isopropylethylammonium, hexylmethylammonium, cyclopropylmethylammonium, cyclohexylmethylammonium, allylmethylammonium, benzylmethylammonium and 4-methylcyclohexylethylammonium groups. Any two of T4, T5 and T6 may form, along with the nitrogen atom to which they are bonded, a heterocyclic, 5-, 6-, 7- or 8-membered ammonium group optionally having oxygen, nitrogen and/or sulfur atoms.
The methoxy group substituted by a phenyl group optionally substituted by a halogen atom or a C1-C4 alkyl group for G includes, for example, benzyloxy, 2-chlorobenzyloxy, 3-chlorobenzyloxy, 4-chlorobenzyloxy, 3-methylbenzyloxy, 4-t-butylbenzyloxy, 2,6-difluorobenzyloxy and 2-fluoro-4-chlorobenzyloxy groups.
The heterocyclic, 5-, 6-, 7- or 8-membered ammonium group optionally having oxygen, nitrogen and/or sulfur atoms, which is formed by two of T4, T5 and T6 along with the nitrogen atom to which they are bonded, includes, for example, pyrrolidine, pyrazolidine, imidazolidine, oxazolidine, isoxazolidine, thiazolidine, piperazine, piperazine, morpholine, thiamorpholine, hexamethylenimine and heptamethylenimine groups. The haloalkylsulfenyl group for G, R, W, X, Y and Z may be a straight chain or branched C1-C4 haloalkylthio group, including, for example, fluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, fluoroethylthio, pentafluoroethylthio and fluoro-iso-propylthio groups.
The haloalkylsulfinyl group for G, R, W, X, Y and Z may be a straight chain or branched, C1-C4 haloalkylsulfinyl group, including, for example, fluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, fluorcethylsulfinyl, pentafluoroethylsulfinyl and fluoro-iso-propylsulfinyl groups.
The haloalkylsulfonyl group for G, R, W, X, Y and Z may be a straight chain or branched, C2-C4 haloalkylsulfonyl group, including, for example, fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, ftuoroethylsulfonyl, pentafluoroethylsulfonyl and fluoro-isopropylsulfonyl groups.
The heloalkenyl group for G, R, T1 and W may be a straight chain or branched C2-C4 haloalkenyl group, including, for example, 2-chloroethenyl, 2-bromoethenyl-and 2,2-dichloroethenyl groups.
The alkenyloxy group for G, R, R1, T1, W, Y and Y1 may be a straight chain or branched C2-C4 alkenyloxy group, including, for example, allyloxy, 2-propenyloxy, 2-butenyloxy and 2-methyl-2-propenyloxy groups.
The haloalkenyloxy group for G, R, W and Y may be a straight chain or branched C2-C5 haloalkenyloxy group, including, for example, 3-chloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 4-chloro-2-butenyloxy, 4,4-dichloro-3-butenyloxy and 4,4-difluoro-3-butenyloxy groups.
The alkenylsulfenyl group for G, R, W, X, Y and Z may be a straight chain or branched C2-C4 alkenylsulfenyl group, including, for example, allylsulfenyl, 2-propenylsulfenyl, 2-butenylsulfenyl and 2-methyl-2-propenylsulfenyl groups.
The alkenylsulfinyl group for G, R, W, X, Y and Z may be a straight chain or branched C2-C5 alkenylsulfinyl group, including, for example, allylsulfinyl, 2-propenylsulfinyl, 2-butenylsulfinyl and 2-methyl-2-propenylsulfinyl groups.
The alkenylsulfonyl group for G, R, W, X, Y and Z may be a straight chain or branched C2-C4 alkenylsulfonyl group, including, for example, allylsulfonyl, 2-propenylsulfonyl, 2-butenylsulfonyl and 2-methyl-2-propenylsulfonyl groups.
The haloalkenylsulfenyl group for G, R, W and Y may be a straight chain or branched C, C, haloalkenylsulfenyl group, including, for example, 3-chloro-2-propenylsulfenyl, 4-chloro-2-butenylsulfenyl, 3,3-dichloro-2-propenylsulfenyl, 4,4-dichloro-3-butenylsulfenyl and 4,4-difluoro-3-butenylsulfenyl groups.
The haloalkenylsulfinyl group for G, R, W and Y may be a straight chain or branched C2-C4 haloalkenylsulfinyl group, including, for example, 3-chloro-2-propenylsulfinyl, 3,3-dichloro-2-propenylsulfinyl, 4-chloro-2-butenylsulfinyl, 4,4-dichloro-3-butenylsulfinyl and 4,4-difluoro-3-butenylsulfinyl groups.
The haloalkenylsulfonyl group for G, R, W and Y may be a straight chain or branched C2-C4 haloalkenylsulfonyl group, including, for example, 3-chloro-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl, 4-chloro-2-butenylsulfonyl, 4,4-dichloro-3-butenylsulfonyl and 4,4-difluoro-3-butenylsulfonyl groups.
The C2-C4 haloalkynyl group for G, R and W includes, for example, chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-1-propynyl and 3-bromo-1-butynyl groups.
The C2-C4 alkenyloxy group for G, R, W and Y includes, for example, 2-propynyloxy, 2-butenyloxy and 1-methyl-2-propynyloxy groups.
The C2-C4 haloalkenyloxy group for G, R, W and Y includes, for example, 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy and 3-iodo-2-propynyloxy groups.
The C2-C6 alkenylsulfenyl group for G, R, W and Y includes, for example, 2-propynylsulfenyl, 2-butynylsulfenyl and 1-methyl-2-propynylsulfenyl groups.
The C2-C6 alkenylsulfinyl group for G, R, W and Y includes, for example, 2-propynylsulfinyl, 2-butenylsulfinyl and 1-methyl-2-propynylsulfinyl groups.
The C2-C6 alkenylsulfonyl group for G, R, W and Y includes, for example, 2-propynylsulfonyl, 2-butynylsulfonyl and 1-methyl-2-propynylsulfonyl groups.
The C2-C6 haloalkenylsulfenyl group for G, R, W and Y includes, for example, 3-chloro-2-propynylsulfenyl, 3-bromo-2-propynylsulfenyl and 3-iodo-2-propynylsulfenyl groups.
The C2-C6 haloalkenylsulfinyl group for G, R, W and Y includes, for example, 3-chloro-2-propynylsulfinyl, 3-bromo-2-propynylsulfinyl and 3-iodo-2-propynylsulfinyl groups.
The C2-C6 haloalkynylsulfonyl group for G, R, W and Y includes, for example, 3-chloro-2-propynylsulfonyl, 3-bromo-2-propynylsulfonyl and 3-iodo-2-propynylsulfonyl groups.
The C2-C4 alkylcarbonyloxy group for G, R, W and Y includes, for example, acetoxy, propanoyloxy, butanoyloxy and isopropylcarbonyloxy groups.
The benzoyl group optionally substituted by X for E and G includes, for example, benzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 4-bromobenzoyl, 4-fluorobenzoyl, 3-methylbenzoyl, 4-methylbenzoyl, 4-tert-butylbenzoyl and 3,4-dichlorobenzoyl groups.
Even at low concentration, the compounds of the present invention effectively prevent various pests, which include, for example, so-called agricultural insect pests that injure agricultural and horticultural crops and trees, so-called live-stock insect pests that live on livestock and poultry, so-called sanitary insect pests that have various negative influences on the human living environment including houses, so-called stored products insect pests that injure grains stored in storehouses, and also acarids, nematodes, molluscs and crustaceans that live in the same sites as above and injure those mentioned above.
Examples of insect pests, stands, nematodes, molluscs and crustaceans capable of being exterminated by the compounds of the present invention are mentioned below, which, however, are not limitative.
Insect pests of Lepidoptera, such as rice stem borer (Chilo suppressalis Walker), rice leafroller (Cnaphalocrocis medinalis Guenée), green rice caterpillar (Naranga aenescens Moore), rice skipper (Parnara guttata Bremer et Gvey), diamond back moths (Plutella xylostella Linneé), cabbage armyworms (Mamestra brassicae Linneé), common white (Pieris rapae crucivora Boisduval), turnip moth (Agrotis segetum Denis et Schiffermüller), common cutworn (Spodptera litura Fabricius), beet armyworm (Spodoptera exigua Hübner), smaller tea tortrix (Adoxophyes sp.), oriental tea tortrix (Homona magnanima Diakonoff), peach fruit moth (Carposina niponensis Walsingham), oriental fruit moth (Grapholita molests Busck), summer fruit tortrix (Adoxophyes orana fascists Walsingham), apple leafminers (Phyllonorycter ringoniella Matsumura), corn earworm (Helicoverpo zea Boddie), tobacco bad worms (Heliothis virescens Fabricius), European corn borer (Ostrinia nubilalis Hübner), fall armyworm (Spodoptera frugiperda J. E. Smith), Codling moth moth (Cydia pomonella Linneé), fall webworms (Hyphantria cunea Drury), etc.;
Insect pests of Hemiptera, such as green rice leafhopper (Nephotettix cincticeps Uhler), brown rice planthoppers (Nilaparvata lugens Stal), green peach aphid (Myzus persicae Sulzer), cotton aphid (Aphis gossypii Glover), green-house whitefly (Trialeurodes vaporariorum Westwood), sweetpotato white fly (Bemisia tabaci Gennadius), pear psylla (Psylla pyricola Forster), azalea lace bug (Stephanitis pyrioides Scott), arrowhead scale (Unaspis yanonensis Kuwana), comstock mealybug (Pseudococcus comrtocki Kuwana), red wax scale (Ceroplastes rubens Maskell), brown-mamrorated stinkbug (Halyomorpha mists Uhler), cabbage bug (Eurydema rugosam Motschulsky), bed bug (Cimex lectularius Linneé), etc.;
Insect pests of Coleoptera, such as twenty-eight-spotted ladybird (Henosepilachna vigintioctopunctata Fabricius), cupreous chafers (Anomala cuprea Hope), ricewater weevil (Lissorhoptrus oryzophilus Kuschel), sweetpotato weevil (Cylas formicarius Fabricius), cucurbit leaf beetle (Aulacophora femoralis Motschulsky), striped flea beetle (Phyllotreta striolata Fablicius), white-spotted longicom beetle (Anoplophora malasiaca Thomson), pine sawyers (Monochamus alternatus Hope), corn rootworms (Diabrotica spp.), rice weevil (Sitophilus zeamais Motschulsky), lesser rice weevil (Sitophilus oryzae Linneé), granary weevils (Sitophilus granarius Linneé), red four beetle (Tribolium casianeum Herbst), etc.;
Insect pests of Diptera, such as legume leafminer (Liriomyza trifolii Burgess), seedcorn maggot (Delis platura Meigen), Hessia fly (Mayetiola destructor Say), melon fly (Dacus (Zengodacus) cucurbitae Coquillett), Mediterranear fruit fly (Ceratitis capitata Wiedemann), house flies (Musca domestics Linneé), stable fly (Stomoxys calcitrans Linneé), Sheep ked (Melophagus orinus), common cattle grub (Hypoderm lineatum devillers), nothern cattle grub (Hypoderma baris Linneé), sheep botfly (Oestrus ovis Linneé), tsetse fly (Golossina palpalis Robineau-Desvoidy), common gnat (Culex pipiens pollens Coquillett), yellow-fever mosquitoes (Aedes aegypti Linneé), Anopheles culicifacies), etc.
Insect pests of Hymenoptera, such as cabbage sawfly (Athalis rosae ruficornis Jakovlev), pine sawfly (Neodiprion sertifer Geoffroy), chestnut sawfly (Apethymus kuri Takeuchi), etc.;
Insect pests of Thysanoptera, such as melon thrips (Thrips palmi Karny), onion thrips (Thrips tabaci Lindeman), western flower thrips (Frankliniella occidentalis Pergande), flower thrip (Frankliniella intonsa Trybom), yellow tea thrip (Scirtothrips dorsalis Hood), etc.;
Insect pests of Dictyoptera, such as smokybrown cockroache (Periplaneta fuliginosa Serville), Japanese cockroach (Periplaneta japonica Kamy), German cockroaches (Blattella germanica Linneé), etc.;
Insect pests of Orthoptera, such as oriental migratory locust (Locusts migratoria Linneé), rice grasshopper (Oxya yezoensis Shiraki), desert locust (Schistocetca gregaria Forskal), etc.;
Insect pests of Isoptera, such as Formosan subterranean tetmit (Coptotermes formosanus Shiraki), (Reticulitermes Leucotermes speratus Kolbe), (Odontotermes formosanus Shirakif), etc.;
Insect pests of Siphonaptera, such as cat fleas (Ctenocephalides felis Bouché), human fleas (Pulex irritans Linneé), oriental rat flea (Xenopsylla cheopis Rothschild), etc.;
Insect pests of Mallophaga, such as Chicken bodylouse (Menacanthus stramineus Nitsch), cattle biting louse (Bavicola bovis Linneé), etc.;
Insect pests of Anoplura, such as short-nosed cattle louse (Haematopinus eurysternus Nitzsh), hog louse (Haematopinus suis Linneé), longnosed cattle louse (Linognathus vituli Linneé), little cattle louse (Solenopates capillatus Enderlein), etc.
Pests of TETRANYCHIDAE, such as citrus red mite (Panonychus cirri McGregor), European red mite (Panonychus ulmi Kock), two-spotted spider mite (Tetranychus urticae Koch), Kanzawa spinder mite (Tetranychus kanzawai Kishida), etc.;
Pests of ERIOPHYDAE, such as pink citrus rust mite (Aculops pelekassi Keifor), pear rust mite (Epitrimerus pyri Nalepa), dry bulb mite (Aceria tulipae Keiter), pink tea mite (Acaphylla theae watt), etc.;
Pests of TARSONEMIDAE, such as broad mites (Polyphagotarsonemus lotus Banks), cyclamen mite, strawberry mite (Steneotarsonemus pallidus Banks), etc.;
Pests of ACARIDAE, such as mold mite, copra mite, forage mite (Tyrophagus putrescetiae Schrank), bulb mite (Rhizoglyphus robini Claparede), etc.;
Pests of VARROIDAE, such as bee brood mite (Varroa jacobsoni Oudemans), etc.;
Pests of Ixodidae, such as bull ticks (Boophilus microplus Canestrini), (Haemaphysalis longicornis Neumann), etc.;
Pests of Sarcoptidae, such as sarcoptes mange mite (Sarcaptes scabiei Linneé), etc.;
Nematodes, such as southern root-knot nematode (Meloidogyne incognito Kofoid et White), northern root-knot nematode (Meloidogyne hapla Chitwood), Cobb root-lesion nematode (Pratylenchus penetrous Cobb), walnut root-lesion nematode (Pratylenchus vulnus Allen et Jensen), potato cyst nematode (Globodera rostochiensis Wollenweber), pine wood nematode (Bursaphelenchus xylophilus Steiner et Buhrer), etc.;
Mollusca, such as apple snail (Pomacea canaliculata Lamarck), (Incilaria pilineata Benson), (Acusta despecta sieboldiana Pfeiffer), (Euhadra peliomphala Pfeiffer), pillbug (Armadillidium vulgare Latreille), etc.;
Crustaceans, such as pillbug (Armadillidium vulgare Latreille), etc.
The plant diseases to be controlled by the compounds of the present invention are as follows:
Blast (Pyricularia oryzae), Helminthosporium leaf spot (Cochliobalus miyabeanus) and Sheath blight (Rhizoctonia solani) of rice,
Powdery mildew (Erysiphe graminis f. sp. hordei, f. sp. tritici), Leaf stripe (Pyrenophora graminea), Net blotch (Pyrenophora teres), Fusarium blight (Gibberella zeae), yellow rust, black stem rust and brown rust (Puccinia striijormis, P. graminis, P. recondita and P. hondei), Snow blight and snow mold (Typhula sp., Micronectriella nivais), Loose smut (Ustilago tritici, U. nuda), Eyespot (Pseudocercorsporella herpotrichoides), Scald and leaft blotch (Rhynchosporium secalis), Speckled blotch (Septoria tritici), and Glume blotch (Leptosphaeria nodorum) of barley and wheat,
Melanose (Diaporthe citri), Scab (Elsinoe fawcetti) and Common green mold and blue mold (Penicillium digitatum, P. italicum) of citrus fruit,
Blossom blight (Sclerotinia mali), Canker (Valsa mali), Powder mildew (Podosphaera leucotricha), Alternaria leaft spot (Alternaria mali) and Scab (Yenturia inaequalis) of apple,
Scab (Yenturia nashicola), Black spot (Alternaria Kikuchiana) and Rust (Gymnosporangium haraeanum) of pear,
Brown rot (Sclerotinia cinerea), Scab (Cladosporium carpophilum), and Phomopsis rot (Phomopsis sp.) of peach,
Downy mildew (Plasmopara viticola), Anthracnose (Elsinoe ampelina), Ripe rot (Glomerella cingulata), Powdery mildew (Uncinula nacator) and Rust (Phakopsora Ampelopsidis) of grape,
Anthracnose (Gloesporium kaki), Powdery mildew (Phyllactinia kakicole), Angular leaf spot (Cercospora kaki), and Circular leaf spot (Mycosphaerella nawae) of persimmon,
Downy mildew (Pseudoperenospora cubensis), Anthracnose (Colletotrichum lagenarium), Powdery mildew (Sphaerotheca fuliginea), and Gummy stem blight (Mycosphaerella melonis) of cucurbit.
Late blight (Phytophthora injestans), Early blight (Alternaria solani) and Leaf mold (Cladosporium fulvam) of tomato.
Brown spot (Phomopsis vexans) and Powdery mildew (Erysiphe cichoracoarum) of egg plant,
Alternaria leaft spot (Alternaria japonica) and white spot (Cerocosporella brassicae) of vegetable of the family crucifers.
Rust (Puccinia allii) of Welsh onion.
Purple seed stain (Cercospora kikuchii), Sphaceloma scab (Elsinoe glycines) and Pot and stem blight (Diaporthe phaseololum) of soybean,
Anthracnose (Collectorichum lindemuthianum) of kidney bean.
Leaf spot (Mycosphaerella personatum) and Brown leaf spot (Cercospora arachidicola) of peanut,
Powdery mildew (Erysiphe pisi) of garden pea,
Early blight (Alternaria solani) of potato,
Powdery mildew (Sphaerotheca humuli) of strawberry,
Net blister blight (Exobasidium reticulatum) and White scab (Elsinoe leucospila) of tea,
Brown spot (Alternaria longipes), Powdery mildew (Erysiphe cichoracearum) and Anthracnose (Colletorrichum tabacum) of tobacco,
Cercospora leaft spot (Cercospora beticolo) of sugar beat,
Black spot (Diplocarpon rosae) and Powdery mildew (Sphaerotheca pannosa) of rose,
Leaf spot (Septoria chrysanthemiindici) and Rust (Puccinia horiana) of chrysanthemum,
Grey mold (Botrytis cinerea) of various kinds of crops, and,
Sclerotinia rot (Sclerotinia sclerotiorum) of various kinds of crops.
In addition, the compounds of the present invention are effective in preventing the attachment of aquatic organisms, even at extremely low concentrations. Aquatic organisms to which the invention is directed are, for example, shellfishes and algae, such as mussel, barnacle, oyster, hydrozoan, hydra, Serpula, ascidian, seamoss, Bagula, mud pond snail, sea lettuce, green lever, Ectocarpus, etc.
Specifically, the compounds of the present invention can effectively eztertninete various pests and phytopathogenic microbes of, for example, Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Temitidae, and also mites and louses, even when used at low concentrations. In addition, the compounds of the invention are effective in preventing the attachment of various aquatic organisms living in sea water and fresh water to aquatic constructions, etc. On the other hand, the compounds of the present invention contains useful compounds that have few negative influences on mammals, fishes, shellfishes and useful insects.
Of the compounds of the invention, those having CN as E can be produced according to the following methods (Scheme 1).
Figure USRE038188-20030715-C00025
In (Scheme 1), Q, A and B have the same meanings as defined above; L represents a suitable leaving group, such as a chlorine atom, a bromine atom, an iodine atom, an alkoxy group having from 1 to 4 carbon atoms, a phenoxy group, an alkylsulfonyloxy group having from 1 to 4 carbon atoms, a benzenesulfonyloxy group, a toluenesulfonyloxy group, a phenoxy group, a 1-pyrazolyl group or a 1-imidazolyl group; L′ represents a halogen atom; and alkyl represents an alkyl group preferably having from 1 to 4 carbon atoms. Method A in (Scheme 1) is to react an acetonitrile derivative of formula (3) with an acid chloride, ester or amide of formula (4) or with an acid anhydride of formula (5) to give compounds (1′) of the present invention. The compound (1′) of the invention is optionally reacted with an alkyl halide, an alkyl sulfonate, a trimethylsilyl halide, a sulfonyl chloride, a sulfamoyl chloride, a thiocarbamoyl chloride, an acid chloride or an ester of formula (8) to be converted into compounds (1) of the invention. Depending on the type of B in the compounds (l) of the invention, the compound (1′) is reacted with a dihydropyran, an isocyanate or a thioisocyanate to give the compounds (1). In Method A, if the compound of formula (4) or (5) is used in an excessive amount, the compounds (1) can be directly obtained without isolating the compounds (1′).
Where Q is bonded to the acrylonitrile moiety via a nitrogen atom, compounds (1′) may be produced according to Method B. Method B is to react a heterocyclic compound of formula (6) with a halogenocyanoketone derivative of formula (7) to give compounds (1′) of the invention. Where A is bonded to the acrylonitrile moiety via a nitrogen atom, compounds (1′) may be produced according to Method C. Method C is to react a cyanoacetic acid derivative of formula (9) with a heterocyclic compound of formula (10) to give compounds (1′) of the invention. As the case may be, the compound of formula (9) will be prepared by reacting an acetonitrile derivative of formula (3), such as that used in Method A, with a carbonic acid ester in the presence of a base.
Of the compounds of the invention, those where E is
Figure USRE038188-20030715-C00026
In (Scheme 2), Q, A, E, B, L, L′ and alkyl have the same meanings as above.
Method D in (Scheme 2) is to react a compound of formula (11) with an acid chloride, ester or amide of formula (4) or with an acid anhydride of formula (5) to give the compounds (1′) of the present invention. The compound (1′) of the invention is optionally reacted with an alkyl halide, an alkyl sulfonate, a trimethylsilyl halide, a sulfonyl chloride, a sulfamoyl chloride, a thiocarbamoyl chloride, an acid chloride or an ester of formula (8) to be converted into the compounds (1) of the invention. Depending on the type of B in the compounds (1) of the invention, the compound (1′) is reacted with a dihydropyran, an isocyanate or a thioisocyanate to give the compounds (1). In Method A, if the compound of formula (4) or (5) is used in an excessive amount, the compounds (1) can be directly obtained without isolating the compounds (1′).
Where Q is bonded to the ethylene moiety via a nitrogen atom, the compounds (1′) may be produced according to Method E. Method E is to react a heterocyclic compound of formula (6) with a compound of formula (12) in the presence of a base to give compounds (1′) of the-invention.
Where A is bonded to the ethylene moiety via a nitrogen atom, the compounds (1′) may be produced according to Method F. Method F is to react a compound of formula (13) with a heterocyclic compound of formula (10) through dealcoholation to give the compounds (1′) of the invention. As the case may be, the compound of formula (13) will he prepared by reacting a compound of formula (11), such as that used in Method D, with a carbonic acid ester in the presence of e base.
If desired, the compounds (1′) where E is an alkoxycarbonyl group may be hydrolyzed, decarbozylated and halogenated to give the compounds of the invention where E is a halogen atom. As the case may be, the compounds of the invention where E is a halogen atom may be reacted with a nucleophilic reagent corresponding to E (e.g., triester phosphites, alkyl mercaptans, thiophenols, metal acerylides, metal cyanides, metal azides, nitrites) to give different compounds of the invention. Also as the case may be, the compounds to be obtained through decarboxylation of the compounds (1′) where E is an alkoxycarbonyl group may be reacted with an electrophilic reagent under basic conditions to give the compounds of the invention.
As the case may be, the processes of (Scheme 1) and (Scheme 2) are preferably effected in the presence of a base. The base to be used includes, for example, alkali metal alkoxides such as sodium ethoxide, sodium methoxide and t-butoxy potassium; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; organic bases such as triethylamine, pyridine and DBU; organic lithium compounds such as butyl lithium; lithium amides such as lithium diisopropylamide and lithium bistrimethylsilylamide; and sodium hydride.
The reactions of (Scheme 1) and (Scheme 2) may be effected in a solvent that is inert to the reaction. The solvent includes, for example, lower alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene and toluene; etherd such as diethyl ether, tetrahydrofuran, 1,4-diozane, 1,2-dimethoxyethane and 1,2-diethoxyethane; halogenated hydrocarbons such as methylene chloride, chloroform and 1,2-dichloroethene; amides such as dimethylformamide and dimethylacetamide; acetonitrile; dimethylsulfoxide; and mixed solvents of these. As the case may be, also employable are mixed solvent comprising said solvents and water. Also as the case may be, a quaternary ammonium salt such as tetra-n-butylammonium bromide may be added to the reaction system as a catalyst to obtain good results. The reaction temperature may be freely settled within a range between −30° C. and 200° C. Preferably, the reaction temperature falls between 0° C. and 150° C., or between 0° C. and the boiling point of the solvent if used. The base may be used in an amount of from 0.05 to 10 equivalents, preferably from 0.05 to 3 equivalents, of the reaction substrate.
The compounds of the present invention may be separated from reaction mixtures according to any ordinary methods. If the purification of the compounds of the invention is needed, they can be separated and purified by any ordinary methods of, for example, recrystallization or column chromatography.
Of the compounds of the invention, those having an asymmetric carbon atom include optically-active compounds of (+) forth and (−) form.
Methods of producing the compounds (3) to be used in (Scheme 1) are referred to hereinunder. The compounds (3) can be produced according to the following (Scheme 3).
Figure USRE038188-20030715-C00027
1) A benzyl halide, a benzyl alkylsulfonate, a benzyl arylsulfonate, a halomethyl-heterocyclic compound, an alkylsulfonyloxymethyl-heterocyclic compound or an arylsulfonyloxymethyl-heterocyclic compound of formula (14) is reacted with a suitable cyanating reagent to give compounds (3). Alternatively, a phenylacetic acid derivative or a heterocyclic acetic acid derivative is converted into the corresponding amide derivative, which is then dehydrated to give compounds (3).
2)A heterocyclic halide (15) is condensed with a cyanoacetate (16) in the presence of a base to give a compound (17), which is then hydrolyzed and decarboxylated to give compounds (3).
3) To obtain compounds (3) where Q is bonded to the ethylene moiety via e nitrogen atom, a heterocyclic derivative (6) where the nitrogen atom of Q is unsubstituted is reacted with a haloacetonitrile derivative in the presence of a base. Alternatively, the compound (6) is reacted with a compound (18) in the presence of a base to give a compound (17), said compound (18) being obtained through halogenation of a cyanoacetate, and thereafter the compound (17) is hydrolyzed and decarbozylated to obtain the compounds (3).
The compounds (11) to be used in (Scheme 2) can be produced in the same manner as in the production of the compounds (3) mentioned above.
The compounds (7) to be used in (Scheme I) can be produced by condensing a benzoic acid halide or heterocyclic carboxylic acid halide with a cyanoacetate in the presence of a base followed by halogenating the resulting condensate.
The above-mentioned halomethyl-heterocyclic compounds, alkylsulfonyloxymethyl-heterocyclic compounds and arylsulfonyloxymethyl-heterocyclic compounds can be derived from heterocyclic methane derivatives or heterocyclic carboxylate derivatives that are produced according to ordinary methods (see Alan R. Katritzky, and Charles W. Rees; Comprehensive Heterocyclic Chemistry, Vol. 2, Vol. 3, Vol. 4, Vol. 5 or Vol. 6). To produce the compounds (14) where Q is an oxazol-4-yl or thiazol-4-yl group, a carboxylic acid amide or thioamide can be reacted with 1,3-dichloro-2-propanone.
Examples of the compounds of the present invention are shown in Table 1 to Table 14 below. The abbreviations in these Tables are for the meanings mentioned below:
Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pen: pentyl group, Hex: hexyl group, Hep: heptyl group, Oct: cetyl group, Non: nonyl group, Dec: decyl group, Ph: phenyl group, n: normal, is iso, sec: secondary, t: tertiary, c: cyclo.
Figure USRE038188-20030715-C00028
Figure USRE038188-20030715-C00029
Figure USRE038188-20030715-C00030
Figure USRE038188-20030715-C00031
Figure USRE038188-20030715-C00032
TABLE 1
Figure USRE038188-20030715-C00033
Figure USRE038188-20030715-C00034
Figure USRE038188-20030715-C00035
Figure USRE038188-20030715-C00036
Figure USRE038188-20030715-C00037
Figure USRE038188-20030715-C00038
Figure USRE038188-20030715-C00039
Figure USRE038188-20030715-C00040
Figure USRE038188-20030715-C00041
Figure USRE038188-20030715-C00042
Figure USRE038188-20030715-C00043
Figure USRE038188-20030715-C00044
Figure USRE038188-20030715-C00045
Figure USRE038188-20030715-C00046
Figure USRE038188-20030715-C00047
Figure USRE038188-20030715-C00048
Figure USRE038188-20030715-C00049
Figure USRE038188-20030715-C00050
Figure USRE038188-20030715-C00051
Figure USRE038188-20030715-C00052
Figure USRE038188-20030715-C00053
Figure USRE038188-20030715-C00054
Figure USRE038188-20030715-C00055
Figure USRE038188-20030715-C00056
Figure USRE038188-20030715-C00057
Figure USRE038188-20030715-C00058
Figure USRE038188-20030715-C00059
Figure USRE038188-20030715-C00060
Figure USRE038188-20030715-C00061
Figure USRE038188-20030715-C00062
Figure USRE038188-20030715-C00063
Figure USRE038188-20030715-C00064
Figure USRE038188-20030715-C00065
Figure USRE038188-20030715-C00066
Figure USRE038188-20030715-C00067
Figure USRE038188-20030715-C00068
Figure USRE038188-20030715-C00069
Figure USRE038188-20030715-C00070
Figure USRE038188-20030715-C00071
Figure USRE038188-20030715-C00072
Figure USRE038188-20030715-C00073
Figure USRE038188-20030715-C00074
R1 R2 R3 B Y1 Y2 Y3
2,6-F2—Ph H H H H H H
2,6-F2—Ph H H H H Cl H
2,6-F2—Ph H H H H Me H
2,6-F2—Ph H H H H OMe H
2,6-F2—Ph H H H H SMe H
2,6-F2—Ph H H H H OCF3 H
2,6-F2—Ph H H H H CF3 H
2,6-F2—Ph H H H H CO2Me H
2,6-F2—Ph H H H H H Me
2,6-F2—Ph H H H Me H Me
2,6-F2—Ph H H H Me H CF3
2,6-F2—Ph H H H Me H H
2,6-F2—Ph H H H Me Me Me
2,6-F2—Ph H H H Me Me H
2,6-F2—Ph H H H Me Cl Me
2,6-F2—Ph H H H Me Cl H
2,6-F2—Ph Cl H H Me Cl Me
2,6-F2—Ph H H H Et Me Me
2,6-F2—Ph H H H Et H H
2,6-F2—Ph H H H nPr Me Me
2,6-F2—Ph H H H iPr Me Me
2,6-F2—Ph H H H iPr Cl Me
2,6-F2—Ph H H H nBu Me Me
2,6-F2—Ph H H H tBu Me Me
2,6-F2—Ph H H H Cl Me Me
2,6-F2—Ph H H H Cl Me H
2,6-F2—Ph H H H Cl H Me
2,6-F2—Ph H H H Cl H CF3
2,6-F2—Ph H H H Cl H H
2,6-F2—Ph Me H H Cl H H
2,6-F2—Ph Cl H H Cl H H
2,6-F2—Ph NO2 H H Cl H H
2,6-F2—Ph CO2Me H H Cl H H
2,6-F2—Ph CO2Et H H Cl H H
2,6-F2—Ph H H H Cl Cl Me
2,6-F2—Ph Me H H Cl Cl Me
2,6-F2—Ph H Me H Cl Cl Me
2,6-F2—Ph H Cl H Cl Cl Me
2,6-F2—Ph Cl H H Cl Cl Me
2,6-F2—Ph Cl Cl H Cl Cl Me
2,6-F2—Ph Cl Cl B1 Cl Cl Me
2,6-F2—Ph Ph H H Cl Cl Me
2,6-F2—Ph H Ph H Cl Cl Me
2,6-F2—Ph CF3 H H Cl Cl Me
2,6-F2—Ph H CF3 H Cl Cl Me
2,6-F2—Ph cPr H H Cl Cl Me
2,6-F2—Ph H cPr H Cl Cl Me
2,6-F2—Ph OMe H H Cl Cl Me
2,6-F2—Ph H OMe H Cl Cl Me
2,6-F2—Ph NH2 H H Cl Cl Me
2,6-F2—Ph H NH2 H Cl Cl Me
2,6-F2—Ph NHMe H H Cl Cl Me
2,6-F2—Ph H NHMe H Cl Cl Me
2,6-F2—Ph NMe2 H H Cl Cl Me
2,6-F2—Ph H NMe2 H Cl Cl Me
2,6-F2—Ph NO2 H H Cl Cl Me
2,6-F2—Ph H NO2 H Cl Cl Me
2,6-F2—Ph CN H H Cl Cl Me
2,6-F2—Ph H CN H Cl Cl Me
2,6-F2—Ph OH H H Cl Cl Me
2,6-F2—Ph H OH H Cl Cl Me
2,6-F2—Ph CO2Me H H Cl Cl Me
2,6-F2—Ph H CO2Me H Cl Cl Me
2,6-F2—Ph CO2Et H H Cl Cl Me
2,6-F2—Ph H H H Cl Cl H
2,6-F2—Ph H H H Cl Cl CF3
2,6-F2—Ph H H H Cl Cl CF2H
2,6-F2—Ph H H H Cl Cl CH2OMe
2,6-F2—Ph H H H Cl Cl COMe
2,6-F2—Ph H H H Cl Cl Ph
2,6-F2—Ph H H H Cl Cl CH2Ph
2,6-F2—Ph H H H Cl CF3 Me
2,6-F2—Ph H H H Br Me Me
2,6-F2—Ph H H H Me Br Me
2,6-F2—Ph H H H Me Br H
2,6-F2—Ph H H H Br H H
2,6-F2—Ph H H H OMe Me Me
2,6-F2—Ph H H H Me OMe Me
2,6-F2—Ph H H H OMe H H
2,6-F2—Ph H H H H OMe H
2,6-F2—Ph H H H Cl OMe Me
2,6-F2—Ph H H H OCF3 Me Me
2,6-F2—Ph H H H OCF3 Cl Me
2,6-F2—Ph H H H OCF3 H H
2,6-F2—Ph H H H Me OCF3 Me
2,6-F2—Ph H H H Cl OCF3 Me
2,6-F2—Ph H H H SMe Cl Me
2,6-F2—Ph H H H Me SMe Me
2,6-F2—Ph H H H Cl SMe Me
2,6-F2—Ph H H H SMe H H
2,6-F2—Ph H H H SOMe Cl Me
2,6-F2—Ph H H H Cl SOMe Me
2,6-F2—Ph H H H SOMe H H
2,6-F2—Ph H H H SO2Me Cl Me
2,6-F2—Ph H H H Cl So2Me Me
2,6-F2—Ph H H H SO2Me H H
2,6-F2—Ph H H H CF3 Me Me
2,6-F2—Ph H H H CF3 Cl H
2,6-F2—Ph H H H CF3 Cl Me
2,6-F2—Ph Me H H CF3 Cl Me
2,6-F2—Ph Cl H H CF3 Cl Me
2,6-F2—Ph Br H H CF3 Cl Me
2,6-F2—Ph CF3 H H CF3 Cl Me
2,6-F2—Ph NO2 H H CF3 Cl Me
2,6-F2—Ph CN H H CF3 Cl Me
2,6-F2—Ph CO2Me H H CF3 Cl Me
2,6-F2—Ph CO2Et H H CF3 Cl Me
2,6-F2—Ph H H H CF3 Cl CF3
2,6-F2—Ph H H H CF3 Cl CF2H
2,6-F2—Ph H H H CF3 Cl CH2OMe
2,6-F2—Ph H H H CF3 Cl COCH3
2,6-F2—Ph H H H CF3 H Me
2,6-F2—Ph H H H CF3 H H
2,6-F2—Ph H H H CF3 Br Me
2,6-F2—Ph H H H CF3 SMe Me
2,6-F2—Ph H H H CF3 SOMe Me
2,6-F2—Ph H H H CF3 SO2Me Me
2,6-F2—Ph H H H CF3 CF3 Me
2,6-F2—Ph H H H CF3 NO2 Me
2,6-F2—Ph H H H CF3 CN Me
2,6-F2—Ph H H H CF3 NHMe Me
2,6-F2—Ph H H H CF3 NMe2 Me
2,6-F2—Ph H H H CF3 Ph Me
2,6-F2—Ph H H H CF3 CH2Ph Me
2,6-F2—Ph H H H CF3 OPh Me
2,6-F2—Ph H H H CF3 OH Me
2,6-F2—Ph H H H CF3 CO2Me Me
2,6-F2—Ph H H H CF3 OMe Me
2,6-F2—Ph H H H CF3 OCF3 Me
2,6-F2—Ph H H H CF3 OCF2H Me
2,6-F2—Ph H H H CF3 OCF2H CF2H
2,6-F2—Ph H H H NO2 CF3 Me
2,6-F2—Ph H H H NO2 Cl Me
2,6-F2—Ph H H H NO2 Me Me
2,6-F2—Ph H H H NO2 H H
2,6-F2—Ph H H H Cl NO2 Me
2,6-F2—Ph H H H CN CF3 Me
2,6-F2—Ph H H H CN Cl Me
2,6-F2—Ph H H H CN Me Me
2,6-F2—Ph H H H CN H H
2,6-F2—Ph H H H Cl CN Me
2,6-F2—Ph H H H Br CN Me
2,6-F2—Ph H H H NHMe Me Me
2,6-F2—Ph H H H NHMe Cl Me
2,6-F2—Ph H H H NHMe H H
2,6-F2—Ph H H H Cl NHMe Me
2,6-F2—Ph H H H NMe2 Me Me
2,6-F2—Ph H H H NMe2 Cl Me
2,6-F2—Ph H H H NMe2 H H
2,6-F2—Ph H H H Cl NMe2 Me
2,6-F2—Ph H H H Ph Cl Me
2,6-F2—Ph H H H Ph H H
2,6-F2—Ph H H H Cl Ph Me
2,6-F2—Ph H H H CH2Ph Me Me
2,6-F2—Ph H H H CH2Ph H H
2,6-F2—Ph H H H Cl CH2Ph Me
2,6-F2—Ph H H H OPh H H
2,6-F2—Ph H H H Cl OPh Me
2,6-F2—Ph H H H OH Me Me
2,6-F2—Ph H H H OH H H
2,6-F2—Ph H H H Cl OH Me
2,6-F2—Ph H H H CO2Me Me Me
2,6-F2—Ph H H H CO2Me Cl Me
2,6-F2—Ph H H H CO2Me H H
2,6-F2—Ph H H H cPr Me Me
2,6-F2—Ph H H H cPr Cl Me
2,6-F2—Ph H H B1 Cl Cl Me
2,6-F2—Ph Cl H B1 Cl Cl Me
2,6-F2—Ph H H B2 Cl Cl Me
2,6-F2—Ph H H B3 Cl Cl Me
2,6-F2—Ph H H B4 Cl Cl Me
2,6-F2—Ph Cl H B4 Cl Cl Me
2,6-F2—Ph Cl Me B4 Cl Cl Me
2,6-F2—Ph NO2 H B4 Cl Cl Me
2,6-F2—Ph CO2Me H B4 Cl Cl Me
2,6-F2—Ph CO2Et H B4 Cl Cl Me
2,6-F2—Ph H H B5 Cl Cl Me
2,6-F2—Ph Cl H B5 Cl Cl Me
2,6-F2—Ph H H B6 Cl Cl Me
2,6-F2—Ph Cl H B6 Cl Cl Me
2,6-F2—Ph NO2 H B6 Cl Cl Me
2,6-F2—Ph CO2Me H B6 Cl Cl Me
2,6-F2—Ph CO2Et H B6 Cl Cl Me
2,6-F2—Ph H H B7 Cl Cl Me
2,6-F2—Ph Cl H B7 Cl Cl Me
2,6-F2—Ph NO2 H B7 Cl Cl Me
2,6-F2—Ph CO2Me H B7 Cl Cl Me
2,6-F2—Ph CO2Et H B7 Cl Cl Me
2,6-F2—Ph H H B8 Cl Cl Me
2,6-F2—Ph H H B9 Cl Cl Me
2,6-F2—Ph H H B10 Cl Cl Me
2,6-F2—Ph H H B11 Cl Cl Me
2,6-F2—Ph H H B12 Cl Cl Me
2,6-F2—Ph H H B13 Cl Cl Me
2,6-F2—Ph H H B14 Cl Cl Me
2,6-F2—Ph H H B15 Cl Cl Me
2,6-F2—Ph H H B16 Cl Cl Me
2,6-F2—Ph H H B17 Cl Cl Me
2,6-F2—Ph H H B18 Cl Cl Me
2,6-F2—Ph H H B19 Cl Cl Me
2,6-F2—Ph H H B20 Cl Cl Me
2,6-F2—Ph H H B21 Cl Cl Me
2,6-F2—Ph H H B22 Cl Cl Me
2,6-F2—Ph H H B23 Cl Cl Me
2,6-F2—Ph H H B24 Cl Cl Me
2,6-F2—Ph H H B25 Cl Cl Me
2,6-F2—Ph H H B26 Cl Cl Me
2,6-F2—Ph H H B27 Cl Cl Me
2,6-F2—Ph H H B28 Cl Cl Me
2,6-F2—Ph H H B29 Cl Cl Me
2,6-F2—Ph H H B30 Cl Cl Me
2,6-F2—Ph H H B31 Cl Cl Me
2,6-F2—Ph H H B32 Cl Cl Me
2,6-F2—Ph H H B33 Cl Cl Me
2,6-F2—Ph H H B34 Cl Cl Me
2,6-F2—Ph H H Na Cl Cl Me
2,6-F2—Ph H H K Cl Cl Me
2,6-F2—Ph H H B1 CF3 Cl Me
2,6-F2—Ph H H B2 CF3 Cl Me
2,6-F2—Ph H H B3 CF3 Cl Me
2,6-F2—Ph H H B4 CF3 Cl Me
2,6-F2—Ph Me H B4 CF3 Cl Me
2,6-F2—Ph Cl H B4 CF3 Cl Me
2,6-F2—Ph NO2 H B4 CF3 Cl Me
2,6-F2—Ph CO2Me H B4 CF3 Cl Me
2,6-F2—Ph CO2Et H B4 CF3 Cl Me
2,6-F2—Ph H H B5 CF3 Cl Me
2,6-F2—Ph Cl H B5 CF3 Cl Me
2,6-F2—Ph H H B6 CF3 Cl Me
2,6-F2—Ph Me H B6 CF3 Cl Me
2,6-F2—Ph Cl H B6 CF3 Cl Me
2,6-F2—Ph NO2 H B6 CF3 Cl Me
2,6-F2—Ph CO2Me H B6 CF3 Cl Me
2,6-F2—Ph CO2Et H B6 CF3 Cl Me
2,6-F2—Ph H H B7 CF3 Cl Me
2,6-F2—Ph Me H B7 CF3 Cl Me
2,6-F2—Ph Cl H B7 CF3 Cl Me
2,6-F2—Ph NO2 H B7 CF3 Cl Me
2,6-F2—Ph CO2Me H B7 CF3 Cl Me
2,6-F2—Ph CO2Et H B7 CF3 Cl Me
2,6-F2—Ph H H B8 CF3 Cl Me
2,6-F2—Ph H H B9 CF3 Cl Me
2,6-F2—Ph H H B10 CF3 Cl Me
2,6-F2—Ph H H B11 CF3 Cl Me
2,6-F2—Ph H H B12 CF3 Cl Me
2,6-F2—Ph H H B13 CF3 Cl Me
2,6-F2—Ph H H B14 CF3 Cl Me
2,6-F2—Ph H H B15 CF3 Cl Me
2,6-F2—Ph H H B16 CF3 Cl Me
2,6-F2—Ph H H B17 CF3 Cl Me
2,6-F2—Ph H H B18 CF3 Cl Me
2,6-F2—Ph H H B19 CF3 Cl Me
2,6-F2—Ph H H B20 CF3 Cl Me
2,6-F2—Ph H H B21 CF3 Cl Me
2,6-F2—Ph H H B22 CF3 Cl Me
2,6-F2—Ph H H B23 CF3 Cl Me
2,6-F2—Ph H H B24 CF3 Cl Me
2,6-F2—Ph H H B25 CF3 Cl Me
2,6-F2—Ph H H B26 CF3 Cl Me
2,6-F2—Ph H H B27 CF3 Cl Me
2,6-F2—Ph H H B28 CF3 Cl Me
2,6-F2—Ph H H B29 CF3 Cl Me
2,6-F2—Ph H H B30 CF3 Cl Me
2,6-F2—Ph H H B31 CF3 Cl Me
2,6-F2—Ph H H B32 CF3 Cl Me
2,6-F2—Ph H H B33 CF3 Cl Me
2,6-F2—Ph H H B34 CF3 Cl Me
2,6-F2—Ph H H Na CF3 Cl Me
2,6-F2—Ph H H K CF3 Cl Me
2,6-F2—Ph H H B1 Cl H H
2,6-F2—Ph H H B2 Cl H H
2,6-F2—Ph H H B3 Cl H H
2,6-F2—Ph H H B4 Cl H H
2,6-F2—Ph Me H B4 Cl H H
2,6-F2—Ph Cl H B4 Cl H H
2,6-F2—Ph NO2 H B4 Cl H H
2,6-F2—Ph CO2Me H B4 Cl H H
2,6-F2—Ph CO2Et H B4 Cl H H
2,6-F2—Ph H H B5 Cl H H
2,6-F2—Ph H H B6 Cl H H
2,6-F2—Ph NO2 H B6 Cl H H
2,6-F2—Ph H H B7 Cl H H
2,6-F2—Ph Me H B7 Cl H H
2,6-F2—Ph Cl H B7 Cl H H
2,6-F2—Ph NO2 H B7 Cl H H
2,6-F2—Ph CO2Me H B7 Cl H H
2,6-F2—Ph CO2Et H B7 Cl H H
2,6-F2—Ph H H B8 Cl H H
2,6-F2—Ph H H B9 Cl H H
2,6-F2—Ph H H B10 Cl H H
2,6-F2—Ph H H B11 Cl H H
2,6-F2—Ph H H B12 Cl H H
2,6-F2—Ph H H B13 Cl H H
2,6-F2—Ph H H B14 Cl H H
2,6-F2—Ph H H B15 Cl H H
2,6-F2—Ph H H B16 Cl H H
2,6-F2—Ph H H B17 Cl H H
2,6-F2—Ph H H B18 Cl H H
2,6-F2—Ph H H B19 Cl H H
2,6-F2—Ph H H B20 Cl H H
2,6-F2—Ph H H B21 Cl H H
2,6-F2—Ph H H B22 Cl H H
2,6-F2—Ph H H B23 Cl H H
2,6-F2—Ph H H B24 Cl H H
2,6-F2—Ph H H B25 Cl H H
2,6-F2—Ph H H B26 Cl H H
2,6-F2—Ph H H B27 Cl H H
2,6-F2—Ph H H B28 Cl H H
2,6-F2—Ph H H B29 Cl H H
2,6-F2—Ph H H B30 Cl H H
2,6-F2—Ph H H B31 Cl H H
2,6-F2—Ph H H B32 Cl H H
2,6-F2—Ph H H B33 Cl H H
2,6-F2—Ph H H B34 Cl H H
2,6-F2—Ph H H Na Cl H H
2,6-F2—Ph H H K Cl H H
tBu H H H H H Me
tBu H H H Me H Me
tBu H H H Me H CF3
tBu H H B7 Me H H
tBu H H H Me Me Me
tBu H H H Me Cl Me
tBu Cl H H Me Cl Me
tBu H H H Et Me Me
tBu H H B8 Et H H
tBu H H H Cl Me Me
tBu H H H Cl Me H
tBu H H H Cl H Me
tBu H H H Cl H CF3
tBu H H H Cl H H
tBu Me H B7 Cl H H
tBu Cl H B7 Cl H H
tBu NO2 H B7 Cl H H
tBu CO2Me H B7 Cl H H
tBu CO2Et H B7 Cl H H
tBu H H H Cl Cl Me
tBu Me H H Cl Cl Me
tBu Cl H H Cl Cl Me
tBu CF3 H H Cl Cl Me
tBu cPr H H Cl Cl Me
tBu OMe H H Cl Cl Me
tBu NO2 H H Cl Cl Me
tBu CN H H Cl Cl Me
tBu CO2Me H H Cl Cl Me
tBu CO2Et H H Cl Cl Me
tBu H H H Cl Cl H
tBu H H H Cl Cl CF3
tBu H H H Cl Cl CF2H
tBu H H H Cl Cl CH2OMe
tBu H H H Cl Cl COMe
tBu H H H Cl CF3 Me
tBu H H H Br Me Me
tBu H H H Me Br Me
tBu H H H Me Br H
tBu H H B34 Br H H
tBu H H H OMe Me Me
tBu H H H Me OMe Me
tBu H H H OMe H H
tBu H H H Cl OMe Me
tBu H H H OCF3 Me Me
tBu H H H OCF3 Cl Me
tBu H H H OCF3 H H
tBu H H H Me OCF3 Me
tBu H H H Cl OCF3 Me
tBu H H H SMe Cl Me
tBu H H H Me SMe Me
tBu H H H Cl SMe Me
tBu H H B7 SMe H H
tBu H H H CF3 Me Me
tBu H H H CF3 Cl H
tBu H H H CF3 Cl Me
tBu Me H H CF3 Cl Me
tBu Cl H H CF3 Cl Me
tBu Br H H CF3 Cl Me
tBu CF3 H H CF3 Cl Me
tBu NO2 H H CF3 Cl Me
tBu CN H H CF3 Cl Me
tBu CO2Me H H CF3 Cl Me
tBu CO2Et H H CF3 Cl Me
tBu H H H CF3 Cl CF3
tBu H H H CF3 Cl CF2H
tBu H H H CF3 Cl CH2OMe
tBu H H H CF3 Cl COCH3
tBu H H H CF3 H Me
tBu H H H CF3 H Me
tBu H H H CF3 Br Me
tBu H H H CF3 SMe Me
tBu H H H CF3 SOMe Me
tBu H H H CF3 SO2Me Me
tBu H H H CF3 CF3 Me
tBu H H H CF3 NO2 Me
tBu H H H CF3 CN Me
tBu H H H CF3 NHMe Me
tBu H H H CF3 NMe2 Me
tBu H H H CF3 OH Me
tBu H H H CF3 CO2Me Me
tBu H H H CF3 OMe Me
tBu H H H CF3 OCF3 Me
tBu H H H CF3 OCF2H Me
tBu H H H CF3 OCF2H CF2H
tBu H H H NO2 Cl Me
tBu H H H NO2 Me Me
tBu H H H NO2 H H
tBu H H H Cl NO2 Me
tBu H H H CN Cl Me
tBu H H H CN Me Me
tBu H H H CN H H
tBu H H H Cl CN Me
tBu H H H NMe2 H H
tBu H H H Cl NMe2 Me
tBu H H H OH Me Me
tBu H H H OH H H
tBu H H H Cl OH Me
tBu H H H CO2Me Me Me
tBu H H H CO2Me Cl Me
tBu H H H CO2Me H H
tBu H H B1 Cl Cl Me
tBu Cl H B1 Cl Cl Me
tBu H H B2 Cl Cl Me
tBu H H B3 Cl Cl Me
tBu H H B4 Cl Cl Me
tBu Me H B4 Cl Cl Me
tBu Cl H B4 Cl Cl Me
tBu NO2 H B4 Cl Cl Me
tBu CO2Me H B4 Cl Cl Me
tBu CO2Et H B4 Cl Cl Me
tBu H H B5 Cl Cl Me
tBu H H B6 Cl Cl Me
tBu Cl H B6 Cl Cl Me
tBu H H B7 Cl Cl Me
tBu Me H B7 Cl Cl Me
tBu Cl H B7 Cl Cl Me
tBu NO2 H B7 Cl Cl Me
tBu CO2Me H B7 Cl Cl Me
tBu CO2Et H B7 Cl Cl Me
tBu H H B8 Cl Cl Me
tBu H H B9 Cl Cl Me
tBu H H B10 Cl Cl Me
tBu H H B11 Cl Cl Me
tBu H H B12 Cl Cl Me
tBu H H B13 Cl Cl Me
tBu H H B14 Cl Cl Me
tBu H H B15 Cl Cl Me
tBu H H B16 Cl Cl Me
tBu H H B17 Cl Cl Me
tBu H H B18 Cl Cl Me
tBu H H B19 Cl Cl Me
tBu H H B20 Cl Cl Me
tBu H H B21 Cl Cl Me
tBu H H B22 Cl Cl Me
tBu H H B23 Cl Cl Me
tBu H H B24 Cl Cl Me
tBu H H B25 Cl Cl Me
tBu H H B26 Cl Cl Me
tBu H H B27 Cl Cl Me
tBu H H B28 Cl Cl Me
tBu H H B29 Cl Cl Me
tBu H H B30 Cl Cl Me
tBu H H B31 Cl Cl Me
tBu H H B32 Cl Cl Me
tBu H H B33 Cl Cl Me
tBu H H B34 Cl Cl Me
tBu H H Na Cl Cl Me
tBu H H K Cl Cl Me
tBu H H B1 CF3 Cl Me
tBu H H B2 CF3 Cl Me
tBu H H B3 CF3 Cl Me
tBu H H B4 CF3 Cl Me
tBu Me H B4 CF3 Cl Me
tBu Cl H B4 CF3 Cl Me
tBu NO2 H B4 CF3 Cl Me
tBu CO2Me H B4 CF3 Cl Me
tBu CO2Et H B4 CF3 Cl Me
tBu H H B5 CF3 Cl Me
tBu H H B6 CF3 Cl Me
tBu Cl H B6 CF3 Cl Me
tBu H H B7 CF3 Cl Me
tBu Me H B7 CF3 Cl Me
tBu Cl H B7 CF3 Cl Me
tBu NO2 H B7 CF3 Cl Me
tBu CO2Me H B7 CF3 Cl Me
tBu CO2Et H B7 CF3 Cl Me
tBu H H B8 CF3 Cl Me
tBu H H B9 CF3 Cl Me
tBu H H B10 CF3 Cl Me
tBu H H B11 CF3 Cl Me
tBu H H B12 CF3 Cl Me
tBu H H B13 CF3 Cl Me
tBu H H B14 CF3 Cl Me
tBu H H B15 CF3 Cl Me
tBu H H B16 CF3 Cl Me
tBu H H B17 CF3 Cl Me
tBu H H B18 CF3 Cl Me
tBu H H B19 CF3 Cl Me
tBu H H B20 CF3 Cl Me
tBu H H B21 CF3 Cl Me
tBu H H B22 CF3 Cl Me
tBu H H B23 CF3 Cl Me
tBu H H B24 CF3 Cl Me
tBu H H B25 CF3 Cl Me
tBu H H B26 CF3 Cl Me
tBu H H B27 CF3 Cl Me
tBu H H B28 CF3 Cl Me
tBu H H B29 CF3 Cl Me
tBu H H B30 CF3 Cl Me
tBu H H B31 CF3 Cl Me
tBu H H B32 CF3 Cl Me
tBu H H B33 CF3 Cl Me
tBu H H B34 CF3 Cl Me
tBu H H Na CF3 Cl Me
tBu H H K CF3 Cl Me
tBu H H B1 Cl H H
tBu H H B2 Cl H H
tBu H H B3 Cl H H
tBu H H B4 Cl H H
tBu H H B5 Cl H H
tBu H H B6 Cl H H
tBu H H B7 Cl H H
tBu H H B8 Cl H H
tBu H H B9 Cl H H
tBu H H B10 Cl H H
tBu H H B11 Cl H H
tBu H H B12 Cl H H
tBu H H B13 Cl H H
tBu H H B14 Cl H H
tBu H H B15 Cl H H
tBu H H B16 Cl H H
tBu H H B17 Cl H H
tBu H H B18 Cl H H
tBu H H B19 Cl H H
tBu H H B20 Cl H H
tBu H H B21 Cl H H
tBu H H B22 Cl H H
tBu H H B23 Cl H H
tBu H H B24 Cl H H
tBu H H B25 Cl H H
tBu H H B26 Cl H H
tBu H H B27 Cl H H
tBu H H B28 Cl H H
tBu H H B29 Cl H H
tBu H H B30 Cl H H
tBu H H B31 Cl H H
tBu H H B32 Cl H H
tBu H H B33 Cl H H
tBu H H B34 Cl H H
tBu H H Na Cl H H
tBu H H K Cl H H
2-pyridyl H H H H H Me
2-pyridyl H H H Me H Me
2-pyridyl H H H Me H CF3
2-pyridyl H H B7 Me H H
2-pyridyl H H H Me Me Me
2-pyridyl H H H Me Cl Me
2-pyridyl Cl H H Me Cl Me
2-pyridyl H H H Et Me Me
2-pyridyl H H H Et H H
2-pyridyl H H H Cl Me Me
2-pyridyl H H H Cl Me H
2-pyridyl H H H Cl H Me
2-pyridyl H H H Cl H CF3
2-pyridyl H H B7 Cl H H
2-pyridyl Me H B7 Cl H H
2-pyridyl Cl H B7 Cl H H
2-pyridyl CF3 H B7 Cl H H
2-pyridyl cPr H B7 Cl H H
2-pyridyl OMe H B7 Cl H H
2-pyridyl NO2 H B7 Cl H H
2-pyridyl CN H B7 Cl H H
2-pyridyl CO2Me H B7 Cl H H
2-pyridyl CO2Et H B7 Cl H H
2-pyridyl H H H Cl Cl Me
2-pyridyl Me H H Cl Cl Me
2-pyridyl Cl H H Cl Cl Me
2-pyridyl CF3 H H Cl Cl Me
2-pyridyl cPr H H Cl Cl Me
2-pyridyl OMe H H Cl Cl Me
2-pyridyl NO2 H H Cl Cl Me
2-pyridyl CN H H Cl Cl Me
2-pyridyl CO2Me H H Cl Cl Me
2-pyridyl CO2Et H H Cl Cl Me
2-pyridyl H H H Cl Cl H
2-pyridyl H H H Cl Cl CF3
2-pyridyl H H H Cl Cl CF2H
2-pyridyl H H H Cl Cl CH2OMe
2-pyridyl H H H Cl Cl COMe
2-pyridyl H H H Cl CF3 Me
2-pyridyl H H H Br Me Me
2-pyridyl H H H Me Br Me
2-pyridyl H H H Me Br H
2-pyridyl H H H Br H H
2-pyridyl H H H OMe Me Me
2-pyridyl H H H Me OMe Me
2-pyridyl H H B7 OMe H H
2-pyridyl H H H Cl OMe Me
2-pyridyl H H H OCF3 Me Me
2-pyridyl H H H OCF3 Cl Me
2-pyridyl H H B7 OCF3 H H
2-pyridyl H H H Me OCF3 Me
2-pyridyl H H H Cl OCF3 Me
2-pyridyl H H H SMe Cl Me
2-pyridyl H H H Me SMe Me
2-pyridyl H H H Cl SMe Me
2-pyridyl H H B7 SMe H H
2-pyridyl H H H CF3 Me Me
2-pyridyl H H H CF3 Cl H
2-pyridyl H H H CF3 Cl Me
2-pyridyl Me H H CF3 Cl Me
2-pyridyl Cl H H CF3 Cl Me
2-pyridyl Br H H CF3 Cl Me
2-pyridyl CF3 H H CF3 Cl Me
2-pyridyl NO2 H H CF3 Cl Me
2-pyridyl CN H H CF3 Cl Me
2-pyridyl CO2Me H H CF3 Cl Me
2-pyridyl CO2Et H H CF3 Cl Me
2-pyridyl H H H CF3 Cl CF3
2-pyridyl H H H CF3 Cl CF2H
2-pyridyl H H H CF3 Cl CH2OMe
2-pyridyl H H H CF3 Cl COCH3
2-pyridyl H H H CF3 H Me
2-pyridyl H H H CF3 H H
2-pyridyl H H H CF3 Br Me
2-pyridyl H H H CF3 SMe Me
2-pyridyl H H H CF3 SOMe Me
2-pyridyl H H H CF3 SO2Me Me
2-pyridyl H H H CF3 CF3 Me
2-pyridyl H H H CF3 NO2 Me
2-pyridyl H H H CF3 CN Me
2-pyridyl H H H CF3 NHMe Me
2-pyridyl H H H CF3 NMe2 Me
2-pyridyl H H H CF3 OH Me
2-pyridyl H H H CF3 CO2Me Me
2-pyridyl H H H CF3 OMe Me
2-pyridyl H H H CF3 OCF3 Me
2-pyridyl H H H CF3 OCF2H Me
2-pyridyl H H H CF3 OCF2H CF2H
2-pyridyl H H H NO2 Cl Me
2-pyridyl H H H NO2 Me Me
2-pyridyl H H B7 NO2 H H
2-pyridyl H H H Cl NO2 Me
2-pyridyl H H H CN Cl Me
2-pyridyl H H H CN Me Me
2-pyridyl H H H CN H H
2-pyridyl H H H Cl CN Me
2-pyridyl H H H NMe2 H H
2-pyridyl H H H Cl NMe2 Me
2-pyridyl H H H OH Me Me
2-pyridyl H H H OH H H
2-pyridyl H H H Cl OH Me
2-pyridyl H H H CO2Me Me Me
2-pyridyl H H H CO2Me Cl Me
2-pyridyl H H H CO2Me H H
2-pyridyl H H B1 Cl Cl Me
2-pyridyl H H B2 Cl Cl Me
2-pyridyl H H B3 Cl Cl Me
2-pyridyl H H B4 Cl Cl Me
2-pyridyl H H B5 Cl Cl Me
2-pyridyl H H B6 Cl Cl Me
2-pyridyl H H B7 Cl Cl Me
2-pyridyl Cl H B7 Cl Cl Me
2-pyridyl H H B8 Cl Cl Me
2-pyridyl H H B9 Cl Cl Me
2-pyridyl H H B10 Cl Cl Me
2-pyridyl H H B11 Cl Cl Me
2-pyridyl H H B12 Cl Cl Me
2-pyridyl H H B13 Cl Cl Me
2-pyridyl H H B14 Cl Cl Me
2-pyridyl H H B15 Cl Cl Me
2-pyridyl H H B16 Cl Cl Me
2-pyridyl H H B17 Cl Cl Me
2-pyridyl H H B18 Cl Cl Me
2-pyridyl H H B19 Cl Cl Me
2-pyridyl H H B20 Cl Cl Me
2-pyridyl H H B21 Cl Cl Me
2-pyridyl H H B22 Cl Cl Me
2-pyridyl H H B23 Cl Cl Me
2-pyridyl H H B24 Cl Cl Me
2-pyridyl H H B25 Cl Cl Me
2-pyridyl H H B26 Cl Cl Me
2-pyridyl H H B27 Cl Cl Me
2-pyridyl H H B28 Cl Cl Me
2-pyridyl H H B29 Cl Cl Me
2-pyridyl H H B30 Cl Cl Me
2-pyridyl H H B31 Cl Cl Me
2-pyridyl H H B32 Cl Cl Me
2-pyridyl H H B33 Cl Cl Me
2-pyridyl H H B34 Cl Cl Me
2-pyridyl H H Na Cl Cl Me
2-pyridyl H H K Cl Cl Me
2-pyridyl H H B1 CF3 Cl Me
2-pyridyl H H B2 CF3 Cl Me
2-pyridyl H H B3 CF3 Cl Me
2-pyridyl H H B4 CF3 Cl Me
2-pyridyl Cl H B4 CF3 Cl Me
2-pyridyl CO2Me H B4 CF3 Cl Me
2-pyridyl H H B5 CF3 Cl Me
2-pyridyl H H B6 CF3 Cl Me
2-pyridyl H H B7 CF3 Cl Me
2-pyridyl Cl H B7 CF3 Cl Me
2-pyridyl NO2 H B7 CF3 Cl Me
2-pyridyl CO2Me H B7 CF3 Cl Me
2-pyridyl H H B8 CF3 Cl Me
2-pyridyl H H B9 CF3 Cl Me
2-pyridyl H H B10 CF3 Cl Me
2-pyridyl H H B11 CF3 Cl Me
2-pyridyl H H B12 CF3 Cl Me
2-pyridyl H H B13 CF3 Cl Me
2-pyridyl H H B14 CF3 Cl Me
2-pyridyl H H B15 CF3 Cl Me
2-pyridyl H H B16 CF3 Cl Me
2-pyridyl H H B17 CF3 Cl Me
2-pyridyl H H B18 CF3 Cl Me
2-pyridyl H H B19 CF3 Cl Me
2-pyridyl H H B20 CF3 Cl Me
2-pyridyl H H B21 CF3 Cl Me
2-pyridyl H H B22 CF3 Cl Me
2-pyridyl H H B23 CF3 Cl Me
2-pyridyl H H B24 CF3 Cl Me
2-pyridyl H H B25 CF3 Cl Me
2-pyridyl H H B26 CF3 Cl Me
2-pyridyl H H B27 CF3 Cl Me
2-pyridyl H H B28 CF3 Cl Me
2-pyridyl H H B29 CF3 Cl Me
2-pyridyl H H B30 CF3 Cl Me
2-pyridyl H H B31 CF3 Cl Me
2-pyridyl H H B32 CF3 Cl Me
2-pyridyl H H B33 CF3 Cl Me
2-pyridyl H H B34 CF3 Cl Me
2-pyridyl H H Na CF3 Cl Me
2-pyridyl H H K CF3 Cl Me
2-pyridyl H H B1 Cl H H
2-pyridyl H H B2 Cl H H
2-pyridyl H H B3 Cl H H
2-pyridyl H H B4 Cl H H
2-pyridyl Me H B4 Cl H H
2-pyridyl Cl H B4 Cl H H
2-pyridyl NO2 H B4 Cl H H
2-pyridyl CO2Me H B4 Cl H H
2-pyridyl CO2Et H B4 Cl H H
2-pyridyl H H B5 Cl H H
2-pyridyl H H B6 Cl H H
2-pyridyl NO2 H B6 Cl H H
2-pyridyl H H B7 Cl H H
2-pyridyl Me H B7 Cl H H
2-pyridyl Cl H B7 Cl H H
2-pyridyl NO2 H B7 Cl H H
2-pyridyl CO2Me H B7 Cl H H
2-pyridyl CO2Et H B7 Cl H H
2-pyridyl H H B8 Cl H H
2-pyridyl H H B9 Cl H H
2-pyridyl H H B10 Cl H H
2-pyridyl H H B11 Cl H H
2-pyridyl H H B12 Cl H H
2-pyridyl H H B13 Cl H H
2-pyridyl H H B14 Cl H H
2-pyridyl H H B15 Cl H H
2-pyridyl H H B16 Cl H H
2-pyridyl H H B17 Cl H H
2-pyridyl H H B18 Cl H H
2-pyridyl H H B19 Cl H H
2-pyridyl H H B20 Cl H H
2-pyridyl H H B21 Cl H H
2-pyridyl H H B22 Cl H H
2-pyridyl H H B23 Cl H H
2-pyridyl H H B24 Cl H H
2-pyridyl H H B25 Cl H H
2-pyridyl H H B26 Cl H H
2-pyridyl H H B27 Cl H H
2-pyridyl H H B28 Cl H H
2-pyridyl H H B29 Cl H H
2-pyridyl H H B30 Cl H H
2-pyridyl H H B31 Cl H H
2-pyridyl H H B32 Cl H H
2-pyridyl H H B33 Cl H H
2-pyridyl H H B34 Cl H H
2-pyridyl H H Na Cl H H
2-pyridyl H H K Cl H H
3-pyridyl H H H Cl Cl Me
3-pyridyl H H H CF3 Cl Me
3-pyridyl H H H Cl H H
3-pyridyl H H B4 Cl H H
3-pyridyl H H B7 Cl H H
4-pyridyl H H H Cl Cl Me
4-pyridyl H H H CF3 Cl Me
4-pyridyl H H H Cl H H
4-pyridyl H H B4 Cl H H
4-pyridyl H H B7 Cl H H
3-Me-pyridin-2-yl H H H Cl Cl Me
2-F—Ph H H H Me H Me
2-F—Ph H H H Me Me Me
2-F—Ph H H H Me Cl Me
2-F—Ph H H H Cl H H
2-F—Ph H H H Cl H Me
2-F—Ph H H H Cl H CF3
2-F—Ph H H H Cl Cl Me
2-F—Ph Cl H H Cl Cl Me
2-F—Ph H H B7 OMe H H
2-F—Ph H H B7 SMe H H
2-F—Ph H H H CF3 Me Me
2-F—Ph H H H CF3 Cl Me
2-F—Ph Cl H H CF3 Cl Me
2-F—Ph H H H CF3 H Me
2-F—Ph H H B1 Cl Cl Me
2-F—Ph Cl H B1 Cl Cl Me
2-F—Ph H H B3 Cl Cl Me
2-F—Ph Cl H B4 Cl Cl Me
2-F—Ph H H B6 Cl Cl Me
2-F—Ph H H B7 Cl Cl Me
2-F—Ph Cl H B7 Cl Cl Me
2-F—Ph H H B9 Cl Cl Me
2-F—Ph H H B20 Cl Cl Me
2-F—Ph H H B24 Cl Cl Me
2-F—Ph H H B2 CF3 Cl Me
2-F—Ph H H B3 CF3 Cl Me
2-F—Ph H H B4 CF3 Cl Me
2-F—Ph Cl H B4 CF3 Cl Me
2-F—Ph H H B6 CF3 Cl Me
2-F—Ph H H B7 CF3 Cl Me
2-F—Ph Cl H B7 CF3 Cl Me
2-F—Ph H H B9 CF3 Cl Me
2-F—Ph H H B20 CF3 Cl Me
2-F—Ph H H B24 CF3 Cl Me
2-F—Ph H H B6 Cl H H
2-F—Ph H H B7 Cl H H
3-F—Ph H H H Cl Cl Me
3-F—Ph Cl H H Cl Cl Me
3-F—Ph H H H CF3 Cl Me
3-F—Ph Cl H H CF3 Cl Me
4-F—Ph H H H Cl Cl Me
4-F—Ph Cl H H Cl Cl Me
4-F—Ph H H H CF3 Cl Me
4-F—Ph Cl H H CF3 Cl Me
2,3-F2—Ph H H H Cl Cl Me
2,3-F2—Ph H H H CF3 Cl Me
2,4-F2—Ph H H H Cl Cl Me
2,4-F2—Ph H H H CF3 Cl Me
2,5-F2—Ph H H H Cl Cl Me
2,5-F2—Ph H H H CF3 Cl Me
Ph H H H Me H Me
Ph H H H Me Me Me
Ph H H H Me Cl Me
Ph H H B7 Cl H H
Ph H H H Cl H Me
Ph H H H Cl H CF3
Ph H H H Cl Cl Me
Ph Cl H H Cl Cl Me
Ph H H B7 OMe H H
Ph H H B7 SMe H H
Ph H H H CF3 Me Me
Ph H H H CF3 Cl Me
Ph Cl H H CF3 Cl Me
Ph H H B7 CF3 H Me
Ph H H B1 Cl Cl Me
Ph Cl H B1 Cl Cl Me
Ph H H B3 Cl Cl Me
Ph Cl H B4 Cl Cl Me
Ph H H B6 Cl Cl Me
Ph H H B7 Cl Cl Me
Ph Cl H B7 Cl Cl Me
Ph H H B9 Cl Cl Me
Ph H H B20 Cl Cl Me
Ph H H B24 Cl Cl Me
Ph H H B2 CF3 Cl Me
Ph H H B3 CF3 Cl Me
Ph H H B4 CF3 Cl Me
Ph Cl H B4 CF3 Cl Me
Ph H H B6 CF3 Cl Me
Ph H H B7 CF3 Cl Me
Ph Cl H B7 CF3 Cl Me
Ph H H B9 CF3 Cl Me
Ph H H B20 CF3 Cl Me
Ph H H B24 CF3 Cl Me
Ph H H B6 Cl H H
Ph H H B7 Cl H H
3,4-F2—Ph H H H Cl Cl Me
3,4-F2—Ph H H H CF3 Cl Me
3,5-F2—Ph H H H Cl Cl Me
3,5-F2—Ph H H H CF3 Cl Me
2-Cl—Ph H H H Me H Me
2-Cl—Ph H H H Me Me Me
2-Cl—Ph H H H Me Cl Me
2-Cl—Ph H H H Cl H H
2-Cl—Ph H H H Cl H Me
2-Cl—Ph H H H Cl H CF3
2-Cl—Ph H H H Cl Cl Me
2-Cl—Ph Cl H H Cl Cl Me
2-Cl—Ph H H H OMe H H
2-Cl—Ph H H H SMe H H
2-Cl—Ph H H H CF3 Me Me
2-Cl—Ph H H H CF3 Cl Me
2-Cl—Ph Cl H H CF3 Cl Me
2-Cl—Ph H H H CF3 H Me
2-Cl—Ph H H H Cl Cl Me
2-Cl—Ph Cl H B1 Cl Cl Me
2-Cl—Ph H H B3 Cl Cl Me
2-Cl—Ph Cl H B4 Cl Cl Me
2-Cl—Ph H H B6 Cl Cl Me
2-Cl—Ph H H B7 Cl Cl Me
2-Cl—Ph Cl H B7 Cl Cl Me
2-Cl—Ph H H B9 Cl Cl Me
2-Cl—Ph H H B20 Cl Cl Me
2-Cl—Ph H H B24 Cl Cl Me
2-Cl—Ph H H B2 CF3 Cl Me
2-Cl—Ph H H B3 CF3 Cl Me
2-Cl—Ph H H B4 CF3 Cl Me
2-Cl—Ph Cl H B4 CF3 Cl Me
2-Cl—Ph H H B6 CF3 Cl Me
2-Cl—Ph H H B7 CF3 Cl Me
2-Cl—Ph Cl H B7 CF3 Cl Me
2-Cl—Ph H H B9 CF3 Cl Me
2-Cl—Ph H H B20 CF3 Cl Me
2-Cl—Ph H H B24 CF3 Cl Me
2-Cl—Ph H H B6 Cl H H
2-Cl—Ph H H B7 Cl H H
3-Cl—Ph H H H Cl Cl Me
3-Cl—Ph Cl H H Cl Cl Me
3-Cl—Ph H H H CF3 Cl Me
3-Cl—Ph Cl H H CF3 Cl Me
4-Cl—Ph H H H Cl Cl Me
4-Cl—Ph Cl H H Cl Cl Me
4-Cl—Ph H H H CF3 Cl Me
4-Cl—Ph Cl H H CF3 Cl Me
2,3-Cl2—Ph H H H Cl Cl Me
2,3-Cl2—Ph H H H CF3 Cl Me
2,4-Cl2—Ph H H H Cl Cl Me
2,4-Cl2—Ph H H H CF3 Cl Me
2,5-Cl2—Ph H H H Cl Cl Me
2,5-Cl2—Ph H H H CF3 Cl Me
2,6-Cl2—Ph H H H Me H Me
2,6-Cl2—Ph H H H Me Me Me
2,6-Cl2—Ph H H H Me Cl Me
2,6-Cl2—Ph H H B7 Cl H H
2,6-Cl2—Ph H H H Cl H Me
2,6-Cl2—Ph H H H Cl H CF3
2,6-Cl2—Ph H H H Cl Cl Me
2,6-Cl2—Ph Cl H H Cl Cl Me
2,6-Cl2—Ph H H B7 OMe H H
2,6-Cl2—Ph H H B7 SMe H H
2,6-Cl2—Ph H H H CF3 Me Me
2,6-Cl2—Ph H H H CF3 Cl Me
2,6-Cl2—Ph Cl H H CF3 Cl Me
2,6-Cl2—Ph H H H CF3 H Me
2,6-Cl2—Ph H H B1 Cl Cl Me
2,6-Cl2—Ph Cl H B1 Cl Cl Me
2,6-Cl2—Ph H H B3 Cl Cl Me
2,6-Cl2—Ph Cl H B4 Cl Cl Me
2,6-Cl2—Ph H H B6 Cl Cl Me
2,6-Cl2—Ph H H B7 Cl Cl Me
2,6-Cl2—Ph Cl H B7 Cl Cl Me
2,6-Cl2—Ph H H B9 Cl Cl Me
2,6-Cl2—Ph H H B20 Cl Cl Me
2,6-Cl2—Ph H H B24 Cl Cl Me
2,6-Cl2—Ph H H B2 CF3 Cl Me
2,6-Cl2—Ph H H B3 CF3 Cl Me
2,6-Cl2—Ph H H B4 CF3 Cl Me
2,6-Cl2—Ph Cl H B4 CF3 Cl Me
2,6-Cl2—Ph H H B6 CF3 Cl Me
2,6-Cl2—Ph H H B7 CF3 Cl Me
2,6-Cl2—Ph Cl H B7 CF3 Cl Me
2,6-Cl2—Ph H H B9 CF3 Cl Me
2,6-Cl2—Ph H H B20 CF3 Cl Me
2,6-Cl2—Ph H H B24 CF3 Cl Me
2,6-Cl2—Ph H H B8 Cl H H
2,6-Cl2—Ph H H B15 Cl H H
3,4-Cl2—Ph H H H Cl Cl Me
3,4-Cl2—Ph H H H CF3 Cl Me
3,5-Cl2—Ph H H H Cl Cl Mc
3,5-Cl2—Ph H H H CF3 Cl Me
2-Me—Ph H H H Cl Cl Me
2-Me—Ph H H H CF3 Cl Me
2,6-Me2—Ph H H H Cl Cl Me
2,6-Me2—Ph H H H CF3 Cl Me
2-MeO—Ph H H H Cl Cl Me
2-MeO—Ph H H H CF3 Cl Me
2-MeO—Ph Cl H H CF3 Cl Me
2-CF3O—Ph H H H Cl Cl Me
2-CF3O—Ph H H H CF3 Cl Me
2-SMe—Ph H H H Cl Cl Me
2-SMe—Ph H H H CF3 Cl Me
2-SOMe—Ph H H H Cl Cl Me
2-SOMe—Ph H H H CF3 Cl Me
2-SO2Me—Ph H H H Cl Cl Me
2-SO2Me—Ph H H H CF3 Cl Me
2-CF3—Ph H H H Cl Cl Me
2-CF3—Ph H H H CF3 Cl Me
2-NO2—Ph H H H Cl Cl Me
2-NO2—Ph H H H CF3 Cl Me
2-CN—Ph H H H Cl Cl Me
2-CN—Ph H H H CF3 Cl Me
2-NHMe—Ph H H H Cl Cl Me
2-NHMe—Ph H H H CF3 Cl Me
2-NMe2—Ph H H H Cl Cl Me
2-NMe2—Ph H H H CF3 Cl Me
4-CH2Ph—Ph H H H Cl Cl Me
4-OPh—Ph H H H Cl Cl Me
2-OH—Ph H H H Cl Cl Me
2-OH—Ph H H H CF3 Cl Me
2-CO2Me—Ph H H H Cl Cl Me
2-CO2Me—Ph H H H CF3 Cl Me
2-CO2Et—Ph H H H Cl Cl Me
2-CO2Et—Ph H H H CF3 Cl Me
H CO2Et Ph H Cl Cl Me
Cl CO2Et H H Cl Cl Me
Me Ph H H Cl Cl Me
Et Me H H Cl Cl Me
nPr H H H Cl Cl Me
iPr H H H Cl Cl Me
iPr H H H CF3 Cl Me
nBu H H H Cl Cl Me
nBu H H H CF3 Cl Me
iBu H H H Cl Cl Me
iBu H H H CF3 Cl Me
iBu H H B7 Cl Cl Me
iBu H H B7 CF3 Cl Me
secBu H H H Cl Cl Me
secBu H H H CF3 Cl Me
2,2-Me2-propyl H H H Cl Cl Me
nHex H H H Cl Cl Me
ethenyl H H H Cl Cl Me
1-propenyl H H H Cl Cl Me
1-propenyl H H H CF3 Cl Me
ethynyl H H H Cl Cl Me
1-propynyl H H H Cl Cl Me
1-propynyl H H H CF3 Cl Me
CF3 H H H Cl Cl Me
CF3 H H H CF3 Cl Me
C2F5 H H H Cl Cl Me
C2F5 H H H CF3 Cl Me
2,2-Cl2-cPr H H H Cl Cl Me
2,2-Cl2-cPr H H H CF3 Cl Me
cPr H H H Cl Cl Me
cPr H H H CF3 Cl Me
1-Me-cPr H H H Cl Cl Me
1-Me-cpr H H H CF3 Cl Me
cHex H H H Cl Cl Me
cHex H H H CF3 Cl Me
OMe H H H Cl Cl Me
OtBu H H H Cl Cl Me
OtBu H H H CF3 Cl Me
OCF3 H H H Cl Cl Me
OCF3 H H H CF3 Cl Me
StBu H H H Cl Cl Me
StBu H H H CF3 Cl Me
SOtBu H H H Cl Cl Me
SOtBu H H H CF3 Cl Me
SO2tBu H H H Cl Cl Me
SO2tBu H H H CF3 Cl Me
NO2 H H H Cl Cl Me
NO2 H H H CF3 Cl Me
CN H H H Cl Cl Me
CN H H H CF3 Cl Me
NH2 H H H Cl Cl Me
NH2 H H H CF3 Cl Me
NHMe H H H Cl Cl Me
NHMe H H H CF3 Cl Me
NMe2 H H H Cl Cl Me
NMe2 H H H CF3 Cl Me
CH2Ph H H H Cl Cl Me
CH2Ph H H H CF3 Cl Me
OPh H H H Cl Cl Me
OPh H H H CF3 Cl Me
OH H H H Cl Cl Me
OH H H H CF3 Cl Me
naphthyl-1 H H H Cl Cl Me
naphthyl-1 H H H CF3 Cl Me
naphthyl-2 H H H Cl Cl Me
naphthyl-2 H H H CF3 Cl Me
CO2Me H H H Cl Cl Me
CO2Me H H H CF3 Cl Me
CO2Et H H H Cl Cl Me
CO2Et H H H CF3 Cl Me
2-thienyl H H H Cl Cl Me
2-thienyl H H H CF3 Cl Me
CH2OMe H H H Cl Cl Me
COCH3 H H H Cl Cl Me
—N═CMe2 H H H Cl Cl Me
—N═CMe2 H H H CF3 Cl Me
—(CH2)3— H H Cl Cl Me
—(CH2)3— H H CF3 Cl Me
—(CH2)4— H H Cl Cl Me
—(CH2)4— H H CF3 Cl Me
TABLE 2
Figure USRE038188-20030715-C00075
Figure USRE038188-20030715-C00076
Figure USRE038188-20030715-C00077
Figure USRE038188-20030715-C00078
Figure USRE038188-20030715-C00079
Figure USRE038188-20030715-C00080
Figure USRE038188-20030715-C00081
Figure USRE038188-20030715-C00082
Figure USRE038188-20030715-C00083
Figure USRE038188-20030715-C00084
Figure USRE038188-20030715-C00085
Figure USRE038188-20030715-C00086
Figure USRE038188-20030715-C00087
Figure USRE038188-20030715-C00088
Figure USRE038188-20030715-C00089
Figure USRE038188-20030715-C00090
Figure USRE038188-20030715-C00091
Figure USRE038188-20030715-C00092
Figure USRE038188-20030715-C00093
Figure USRE038188-20030715-C00094
Figure USRE038188-20030715-C00095
Figure USRE038188-20030715-C00096
Figure USRE038188-20030715-C00097
Figure USRE038188-20030715-C00098
Figure USRE038188-20030715-C00099
Figure USRE038188-20030715-C00100
Figure USRE038188-20030715-C00101
Figure USRE038188-20030715-C00102
R1 R2 R3 B Y1 Y2 Y3
2,6-F2—Ph H H H Me H Me
2,6-F2—Ph H H H Me H CF3
2,6-F2—Ph H H H Me H H
2,6-F2—Ph H H H Me Me Me
2,6-F2—Ph H H H Me Cl Me
2,6-F2—Ph Cl H H Me Cl Me
2,6-F2—Ph H H H Et Me Me
2,6-F2—Ph H H H Cl Me Me
2,6-F2—Ph H H H Cl H Me
2,6-F2—Ph H H H Cl H CF3
2,6-F2—Ph H H H Cl H H
2,6-F2—Ph Me H H Cl H H
2,6-F2—Ph Cl H H Cl H H
2,6-F2—Ph H H H Cl Cl Me
2,6-F2—Ph Me H H Cl Cl Me
2,6-F2—Ph H Cl H Cl Cl Me
2,6-F2—Ph Cl H H Cl Cl Me
2,6-F2—Ph CF3 H H Cl Cl Me
2,6-F2—Ph OMe H H Cl Cl Me
2,6-F2—Ph NH2 H H Cl Cl Me
2,6-F2—Ph NHMe H H Cl Cl Me
2,6-F2—Ph NMe2 H H Cl Cl Me
2,6-F2—Ph NO2 H H Cl Cl Me
2,6-F2—Ph CN H H Cl Cl Me
2,6-F2—Ph OH H H Cl Cl Me
2,6-F2—Ph CO2Me H H Cl Cl Me
2,6-F2—Ph CO2Et H H Cl Cl Me
2,6-F2—Ph H H H Cl Cl CF3
2,6-F2—Ph H H H Cl Cl CF2H
2,6-F2—Ph H H H Cl Cl CH2OMe
2,6-F2—Ph H H H Cl Cl COMe
2,6-F2—Ph H H H Cl CF3 Me
2,6-F2—Ph H H H Br Me Me
2,6-F2—Ph H H H Me Br Me
2,6-F2—Ph H H H Me OMe Me
2,6-F2—Ph H H H OMe H H
2,6-F2—Ph H H H OCF3 H H
2,6-F2—Ph H H H SMe H H
2,6-F2—Ph H H H CF3 Me Me
2,6-F2—Ph H H H CF3 Cl Me
2,6-F2—Ph Me H H CF3 Cl Me
2,6-F2—Ph Cl H H CF3 Cl Me
2,6-F2—Ph Br H H CF3 Cl Me
2,6-F2—Ph CF3 H H CF3 Cl Me
2,6-F2—Ph NO2 H H CF3 Cl Me
2,6-F2—Ph CN H H CF3 Cl Me
2,6-F2—Ph CO2Me H H CF3 Cl Me
2,6-F2—Ph CO2Et H H CF3 Cl Me
2,6-F2—Ph H H H CF3 Cl CF3
2,6-F2—Ph H H H CF3 Cl CF2H
2,6-F2—Ph H H H CF3 Cl CH2OMe
2,6-F2—Ph H H H CF3 Cl COCH3
2,6-F2—Ph H H H CF3 H Me
2,6-F2—Ph H H H CF3 Br Me
2,6-F2—Ph H H H CF3 NO2 Me
2,6-F2—Ph H H H CF3 CN Me
2,6-F2—Ph H H H CF3 NHMe Me
2,6-F2—Ph H H H CF3 NMe2 Me
2,6-F2—Ph H H H CF3 CO2Me Me
2,6-F2—Ph H H H CF3 OMe Me
2,6-F2—Ph H H H CF3 OCF2H CF2H
2,6-F2—Ph H H H Cl NO2 Me
2,6-F2—Ph H H H Cl CN Me
2,6-F2—Ph H H H CO2Me Me Me
2,6-F2—Ph H H B1 Cl Cl Me
2,6-F2—Ph H H B2 Cl Cl Me
2,6-F2—Ph H H B3 Cl Cl Me
2,6-F2—Ph H H B4 Cl Cl Me
2,6-F2—Ph H H B5 Cl Cl Me
2,6-F2—Ph H H B6 Cl Cl Me
2,6-F2—Ph H H B7 Cl Cl Me
2,6-F2—Ph H H B8 Cl Cl Me
2,6-F2—Ph H H B9 Cl Cl Me
2,6-F2—Ph H H B10 Cl Cl Me
2,6-F2—Ph H H B11 Cl Cl Me
2,6-F2—Ph H H B12 Cl Cl Me
2,6-F2—Ph H H B13 Cl Cl Me
2,6-F2—Ph H H B14 Cl Cl Me
2,6-F2—Ph H H B15 Cl Cl Me
2,6-F2—Ph H H B16 Cl Cl Me
2,6-F2—Ph H H B17 Cl Cl Me
2,6-F2—Ph H H B18 Cl Cl Me
2,6-F2—Ph H H B19 Cl Cl Me
2,6-F2—Ph H H B20 Cl Cl Me
2,6-F2—Ph H H B21 Cl Cl Me
2,6-F2—Ph H H B22 Cl Cl Me
2,6-F2—Ph H H B23 Cl Cl Me
2,6-F2—Ph H H B24 Cl Cl Me
2,6-F2—Ph H H B25 Cl Cl Me
2,6-F2—Ph H H B26 Cl Cl Me
2,6-F2—Ph H H B27 Cl Cl Me
2,6-F2—Ph H H B28 Cl Cl Me
2,6-F2—Ph H H B29 Cl Cl Me
2,6-F2—Ph H H B30 Cl Cl Me
2,6-F2—Ph H H B31 Cl Cl Me
2,6-F2—Ph H H B32 Cl Cl Me
2,6-F2—Ph H H B33 Cl Cl Me
2,6-F2—Ph H H B34 Cl Cl Me
2,6-F2—Ph H H Na Cl Cl Me
2,6-F2—Ph H H K Cl Cl Me
2,6-F2—Ph H H B2 CF3 Cl Me
2,6-F2—Ph H H B3 CF3 Cl Me
2,6-F2—Ph H H B4 CF3 Cl Me
2,6-F2—Ph H H B5 CF3 Cl Me
2,6-F2—Ph H H B6 CF3 Cl Me
2,6-F2—Ph H H B7 CF3 Cl Me
2,6-F2—Ph H H B8 CF3 Cl Me
2,6-F2—Ph H H B9 CF3 Cl Me
2,6-F2—Ph H H B10 CF3 Cl Me
2,6-F2—Ph H H B11 CF3 Cl Me
2,6-F2—Ph H H B12 CF3 Cl Me
2,6-F2—Ph H H B13 CF3 Cl Me
2,6-F2—Ph H H B14 CF3 Cl Me
2,6-F2—Ph H H B15 CF3 Cl Me
2,6-F2—Ph H H B16 CF3 Cl Me
2,6-F2—Ph H H B17 CF3 Cl Me
2,6-F2—Ph H H B18 CF3 Cl Me
2,6-F2—Ph H H B19 CF3 Cl Me
2,6-F2—Ph H H B20 CF3 Cl Me
2,6-F2—Ph H H B21 CF3 Cl Me
2,6-F2—Ph H H B22 CF3 Cl Me
2,6-F2—Ph H H B23 CF3 Cl Me
2,6-F2—Ph H H B24 CF3 Cl Me
2,6-F2—Ph H H B25 CF3 Cl Me
2,6-F2—Ph H H B26 CF3 Cl Me
2,6-F2—Ph H H B27 CF3 Cl Me
2,6-F2—Ph H H B28 CF3 Cl Me
2,6-F2—Ph H H B29 CF3 Cl Me
2,6-F2—Ph H H B30 CF3 Cl Me
2,6-F2—Ph H H B31 CF3 Cl Me
2,6-F2—Ph H H B32 CF3 Cl Me
2,6-F2—Ph H H B33 CF3 Cl Me
2,6-F2—Ph H H B34 CF3 Cl Me
2,6-F2—Ph H H Na CF3 Cl Me
2,6-F2—Ph H H K CF3 Cl Me
2,6-F2—Ph H H B7 Cl H H
2,6-F2—Ph H H B9 Cl H H
2,6-F2—Ph H H B10 Cl H H
2,6-F2—PhPh H H B11 Cl H H
tBu H H H Me H Me
tBu H H H Me H CF3
tBu H H H Me H H
tBu H H H Me Me Me
tBu H H H Me Cl Me
tBu Cl H H Me Cl Me
tBu H H H Cl Me Me
tBu H H H Cl H Me
tBu H H H Cl H CF3
tBu H H H Cl H H
tBu H H H Cl Cl Me
tBu Me H H Cl Cl Me
tBu Cl H H Cl Cl Me
tBu NO2 H H Cl Cl Me
tBu CO2Me H H Cl Cl Me
tBu CO2Et H H Cl Cl Me
tBu H H H Cl Cl CF3
tBu H H H Cl Cl CF2H
tBu H H H Cl Cl CH2OMe
tBu H H H Cl Cl COMe
tBu H H H Cl CF3 Me
tBu H H H Br Me Me
tBu H H H Me Br Me
tBu H H H OMe H H
tBu H H H CF3 Me Me
tBu H H H CF3 Cl Me
tBu Me H H CF3 Cl Me
tBu Cl H H CF3 Cl Me
tBu NO2 H H CF3 Cl Me
tBu CO2Me H H CF3 Cl Me
tBu CO2Et H H CF3 Cl Me
tBu H H H CF3 Cl CF3
tBu H H H CF3 Cl CF2H
tBu H H H CF3 Cl CH2OMe
tBu H H H CF3 Cl COCH3
tBu H H H CF3 H Me
tBu H H H CF3 NO2 Me
tBu H H H CF3 NHMe Me
tBu H H H CF3 NMe2 Me
tBu H H H NO2 Me Me
tBu H H H CN Cl Me
tBu H H H CN Me Me
tBu H H H Cl CN Me
tBu H H H CO2Me Me Me
tBu H H H CO2Me Cl Me
tBu H H B1 Cl Cl Me
tBu Cl H B1 Cl Cl Me
tBu H H B2 Cl Cl Me
tBu H H B3 Cl Cl Me
tBu H H B4 Cl Cl Me
tBu H H B5 Cl Cl Me
tBu H H B6 Cl Cl Me
tBu H H B7 Cl Cl Me
tBu H H B8 Cl Cl Me
tBu H H B9 Cl Cl Me
tBu H H B10 Cl Cl Me
tBu H H B11 Cl Cl Me
tBu H H B12 Cl Cl Me
tBu H H B13 Cl Cl Me
tBu H H B14 Cl Cl Me
tBu H H B15 Cl Cl Me
tBu H H B16 Cl Cl Me
tBu H H B17 Cl Cl Me
tBu H H B18 Cl Cl Me
tBu H H B19 Cl Cl Me
tBu H H B20 Cl Cl Me
tBu H H B21 Cl Cl Me
tBu H H B22 Cl Cl Me
tBu H H B23 Cl Cl Me
tBu H H B24 Cl Cl Me
tBu H H B25 Cl Cl Me
tBu H H B26 Cl Cl Me
tBu H H B27 Cl Cl Me
tBu H H B28 Cl Cl Me
tBu H H B29 Cl Cl Me
tBu H H B30 Cl Cl Me
tBu H H B31 Cl Cl Me
tBu H H B32 Cl Cl Me
tBu H H B33 Cl Cl Me
tBu H H B34 Cl Cl Me
tBu H H Na Cl Cl Me
tBu H H K Cl Cl Me
tBu H H B2 CF3 Cl Me
tBu H H B3 CF3 Cl Me
tBu H H B4 CF3 Cl Me
tBu H H B5 CF3 Cl Me
tBu H H B6 CF3 Cl Me
tBu H H B7 CF3 Cl Me
tBu H H B8 CF3 Cl Me
tBu H H B9 CF3 Cl Me
tBu H H B10 CF3 Cl Me
tBu H H B11 CF3 Cl Me
tBu H H B12 CF3 Cl Me
tBu H H B13 CF3 Cl Me
tBu H H B14 CF3 Cl Me
tBu H H B15 CF3 Cl Me
tBu H H B16 CF3 Cl Me
tBu H H B17 CF3 Cl Me
tBu H H B18 CF3 Cl Me
tBu H H B19 CF3 Cl Me
tBu H H B20 CF3 Cl Me
tBu H H B21 CF3 Cl Me
tBu H H B22 CF3 Cl Me
tBu H H B23 CF3 Cl Me
tBu H H B24 CF3 Cl Me
tBu H H B25 CF3 Cl Me
tBu H H B26 CF3 Cl Me
tBu H H B27 CF3 Cl Me
tBu H H B28 CF3 Cl Me
tBu H H B29 CF3 Cl Me
tBu H H B30 CF3 Cl Me
tBu H H B31 CF3 Cl Me
tBu H H B32 CF3 Cl Me
tBu H H B33 CF3 Cl Me
tBu H H B34 CF3 Cl Me
tBu H H Na CF3 Cl Me
tBu H H K CF3 Cl Me
tBu H H B7 Cl H H
tBu H H B8 Cl H H
tBu H H B15 Cl H H
tBu H H B17 Cl H H
tBu H H B18 Cl H H
tBu H H B34 Cl H H
2-pyridyl H H H Me H Me
2-pyridyl H H H Me H CF3
2-pyridyl H H B7 Me H H
2-pyridyl H H H Me Me Me
2-pyridyl H H H Me Cl Me
2-pyridyl H H H Cl Me Me
2-pyridyl H H H Cl H Me
2-pyridyl H H H Cl H CF3
2-pyridyl H H H Cl H H
2-pyridyl Cl H H Cl H H
2-pyridyl CO2Me H H Cl H H
2-pyridyl CO2Et H H Cl H H
2-pyridyl H H H Cl Cl Me
2-pyridyl H H H Cl CF3 Me
2-pyridyl H H H Br Me Me
2-pyridyl H H H Me Br Me
2-pyridyl H H B7 OMe H H
2-pyridyl H H H CF3 Me Me
2-pyridyl H H H CF3 Cl Me
2-pyridyl H H H CF3 H Me
2-pyridyl H H B7 CF3 H H
2-pyridyl H H B1 Cl Cl Me
2-pyridyl H H B3 Cl Cl Me
2-pyridyl H H B7 Cl Cl Me
2-pyridyl H H B3 CF3 Cl Me
2-pyridyl H H B7 CF3 Cl Me
2-pyridyl H H B3 Cl H H
2-pyridyl H H B4 Cl H H
2-pyridyl H H B5 Cl H H
2-pyridyl H H B6 Cl H H
2-pyridyl H H B7 Cl H H
2-pyridyl H H B8 Cl H H
2-pyridyl H H B9 Cl H H
2-pyridyl H H B10 Cl H H
2-pyridyl H H B11 Cl H H
2-pyridyl H H B15 Cl H H
2-pyridyl H H B16 Cl H H
2-pyridyl H H B17 Cl H H
2-pyridyl H H B28 Cl H H
2-pyridyl H H B30 Cl H H
2-pyridyl H H B31 Cl H H
2-pyridyl H H B32 Cl H H
2-pyridyl H H B34 Cl H H
3-pyridyl H H H Cl Cl Me
3-pyridyl H H H Cl H H
4-pyridyl H H H Cl Cl Me
4-pyridyl H H H Cl H H
2-F—Ph H H H Cl H H
2-F—Ph H H H Cl Cl Me
2-F—Ph H H B7 OMe H H
2-F—Ph H H B7 SMe H H
2-F—Ph H H H CF3 Cl Me
2-F—Ph H H H CF3 H Me
2-F—Ph H H B1 Cl Cl Me
2-F—Ph H H B3 Cl Cl Me
2-F—Ph H H B6 Cl Cl Me
2-F—Ph H H B7 Cl Cl Me
2-F—Ph Cl H B7 Cl Cl Me
2-F—Ph H H B3 CF3 Cl Me
2-F—Ph H H B6 CF3 Cl Me
2-F—Ph H H B7 CF3 Cl Me
2-F—Ph Cl H B7 CF3 Cl Me
2-F—Ph H H B7 Cl H H
3-F—Ph H H H Cl Cl Me
3-F—Ph H H H CF3 Cl Me
4-F—Ph H H H Cl Cl Me
4-F—Ph H H H CF3 Cl Me
2,3-F2—Ph H H H Cl Cl Me
2,4-F2—Ph H H H Cl Cl Me
2,5-F2—Ph H H H Cl Cl Me
Ph H H H Cl H H
Ph H H H Cl Cl Me
Ph H H H OMe Cl H
Ph H H H SMe Cl H
Ph H H H CF3 Cl Me
Ph H H H CF3 H Me
Ph H H B1 Cl Cl Me
Ph H H B3 Cl Cl Me
Ph H H B6 Cl Cl Me
Ph H H B7 Cl Cl Me
Ph Cl H B7 Cl Cl Me
Ph H H B3 CF3 Cl Me
Ph H H B6 CF3 Cl Me
Ph H H B7 CF3 Cl Me
Ph Cl H B7 CF3 Cl Me
Ph H H B7 Cl H H
Ph H H H Cl Cl Me
Ph H H H Cl Cl Me
2-Cl—Ph H H H Cl H H
2-Cl—Ph H H H Cl Cl Me
2-Cl—Ph H H H OMe H H
2-Cl—Ph H H H SMe H H
2-Cl—Ph H H H CF3 Cl Me
2-Cl—Ph H H H CF3 H Me
2-Cl—Ph H H B1 Cl Cl Me
2-Cl—Ph H H B3 Cl Cl Me
2-Cl—Ph H H B6 Cl Cl Me
2-Cl—Ph H H B7 Cl Cl Me
2-Cl—Ph Cl H B7 Cl Cl Me
2-Cl—Ph H H B3 CF3 Cl Me
2-Cl—Ph H H B6 CF3 Cl Me
2-Cl—Ph H H B7 CF3 Cl Me
2-Cl—Ph Cl H B7 CF3 Cl Me
2-Cl—Ph H H B7 Cl H H
3-Cl—Ph H H H Cl Cl Me
4-Cl—Ph H H H Cl Cl Me
2,3-Cl2—Ph H H H Cl Cl Me
2,4-Cl2—Ph H H H Cl Cl Me
2,5-Cl2—Ph H H H Cl Cl Me
2,6-Cl2—Ph H H H Cl H H
2,6-Cl2—Ph H H H Cl Cl Me
2,6-Cl2—Ph H H H OMe H H
2,6-Cl2—Ph H H H SMe H H
2,6-Cl2—Ph H H H CF3 Cl Me
2,6-Cl2—Ph H H H CF3 H Me
2,6-Cl2—Ph H H B1 Cl Cl Me
2,6-Cl2—Ph H H B3 Cl Cl Me
2,6-Cl2—Ph H H B6 Cl Cl Me
2,6-Cl2—Ph H H B7 Cl Cl Me
2,6-Cl2—Ph Cl H B7 Cl Cl Me
2,6-Cl2—Ph H H B3 CF3 Cl Me
2,6-Cl2—Ph H H B6 CF3 Cl Me
2,6-Cl2—Ph H H B7 CF3 Cl Me
2,6-Cl2—Ph Cl H B7 CF3 Cl Me
2,6-Cl2—Ph H H B7 Cl H H
3,4-Cl2—Ph H H H Cl Cl Me
3,5-Cl2—Ph H H H Cl Cl Me
2-MeO—Ph H H H Cl Cl Me
2-MeO—Ph H H H CF3 Cl Me
2,6-Me2—Ph H H H Cl Cl Me
2,6-Me2—Ph H H H CF3 Cl Me
2-MeO—Ph H H H Cl Cl Me
2-MeO—Ph H H H CF3 Cl Me
2-CF3O—Ph H H H Cl Cl Me
2-SMe—Ph H H H Cl Cl Me
2-SOMe—Ph H H H Cl Cl Me
2-SO2Me—Ph H H H Cl Cl Me
2-CF3—Ph H H H Cl Cl Me
2-NO2—Ph H H H Cl Cl Me
2-CN—Ph H H H Cl Cl Me
2-NHMe—Ph H H H Cl Cl Me
2-NMe2—Ph H H H Cl Cl Me
4-benzyl-Ph H H H Cl Cl Me
4-phenoxy-Ph H H H Cl Cl Me
2-OH—Ph H H H Cl Cl Me
2-CO2Me—Ph H H H Cl Cl Me
2-CO2Et—Ph H H H Cl Cl Me
H CO2Et Ph H Cl Cl Me
Me Ph H H Cl Cl Me
Et Me H H Cl Cl Me
nPr H H H Cl Cl Me
iPr H H H Cl Cl Me
iPr H H H CF3 Cl Me
nBu H H H Cl Cl Me
nBu H H H CF3 Cl Me
iBu H H H Cl Cl Me
iBu H H H CF3 Cl Me
iBu H H B7 Cl Cl Me
iBu H H B7 CF3 Cl Me
iBu H H H Cl Cl H
secBu H H H Cl Cl Me
secBu H H H CF3 Cl Me
2,2-Me2-propyl H H H Cl Cl Me
nHex H H H Cl Cl Me
ethenyl H H H Cl Cl Me
1-propenyl H H H Cl Cl Me
1-propenyl H H H CF3 Cl Me
ethynyl H H H Cl Cl Me
1-propynyl H H H Cl Cl Me
CF3 H H H Cl Cl Me
CHF2 H H H Cl Cl Me
C2H5 H H H Cl Cl Me
2,2-Cl2-cPr H H H Cl Cl Me
2,2-Cl2-cPr H H H CF3 Cl Me
cPr H H H Cl Cl Me
cPr H H H CF3 Cl Me
1-Me-cPr H H H Cl Cl Me
1-Me-cPr H H H CF3 Cl Me
cHex H H H Cl Cl Me
cHex H H H CF3 Cl Me
CH2Ph H H H Cl Cl Me
naphthyl-1 H H H Cl Cl Me
naphthyl-1 H H H CF3 Cl Me
naphthyl-2 H H H Cl Cl Me
CO2Me H H H Cl Cl Me
CO2Et H H H Cl Cl Me
2-thienyl H H H Cl Cl Me
CH2OMe H H H Cl Cl Me
CH2OEt H H H Cl Cl Me
COCH3 H H H Cl Cl Me
COtBu H H H Cl Cl Me
TABLE 3
Figure USRE038188-20030715-C00103
Figure USRE038188-20030715-C00104
Figure USRE038188-20030715-C00105
Figure USRE038188-20030715-C00106
Figure USRE038188-20030715-C00107
Figure USRE038188-20030715-C00108
Figure USRE038188-20030715-C00109
Figure USRE038188-20030715-C00110
Figure USRE038188-20030715-C00111
Figure USRE038188-20030715-C00112
Figure USRE038188-20030715-C00113
Figure USRE038188-20030715-C00114
Figure USRE038188-20030715-C00115
Figure USRE038188-20030715-C00116
Figure USRE038188-20030715-C00117
Figure USRE038188-20030715-C00118
Figure USRE038188-20030715-C00119
Figure USRE038188-20030715-C00120
Figure USRE038188-20030715-C00121
Figure USRE038188-20030715-C00122
Figure USRE038188-20030715-C00123
Figure USRE038188-20030715-C00124
Figure USRE038188-20030715-C00125
Figure USRE038188-20030715-C00126
Figure USRE038188-20030715-C00127
Figure USRE038188-20030715-C00128
Figure USRE038188-20030715-C00129
Figure USRE038188-20030715-C00130
R1 R2 R3 B Y1 Y2
2,6-F2—Ph H H H Me Me
2,6-F2—Ph H H H Et Me
2,6-F2—Ph Me H H Et Me
2,6-F2—Ph Cl H H Et Me
2,6-F2—Ph H Cl H Et Me
2,6-F2—Ph H H H Cl Cl
2,6-F2—Ph H H H Cl Me
2,6-F2—Ph H H H Cl CF3
2,6-F2—Ph H H H Me Cl
2,6-F2—Ph H H H Br Me
2,6-F2—Ph H H H Me Br
2,6-F2—Ph H H H Me CF3
2,6-F2—Ph H H H OMe Me
2,6-F2—Ph H H H OCF3 Me
2,6-F2—Ph H H H SMe Me
2,6-F2—Ph H H H CO2Me Me
2,6-F2—Ph H H H CO2Et Me
2,6-F2—Ph H H H CF3 Me
2,6-F2—Ph H H H CF3 H
2,6-F2—Ph H H B3 CF3 Me
2,6-F2—Ph H H B6 CF3 Me
2,6-F2—Ph H H B7 CF3 Me
2,6-F2—Ph Cl H B7 CF3 Me
tBu H H H Me Me
tBu H H H Et Me
tBu H H H Cl Cl
tBu H H H Cl Me
tBu H H H Me Cl
tBu H H H Cl CF3
tBu H H H Br Me
tBu H H H Me Br
tBu H H H Me CF3
tBu H H H OMe Me
tBu H H H OCF3 Me
tBu H H H SMe Me
tBu H H H CO2Me Me
tBu H H H CO2Et Me
tBu H H H CF3 Me
tBu Me H H CF3 Me
tBu Cl H H CF3 Me
tBu Br H H CF3 Me
tBu CF3 H H CF3 Me
tBu NO2 H H CF3 Me
tBu CN H H CF3 Me
tBu CO2Me H H CF3 Me
tBu CO2Et H H CF3 Me
tBu H H H CF3 H
tBu H H H CF3 Br
tBu H H H CF3 NO2
tBu H H H CF3 CN
tBu H H H CF3 NHMe
tBu H H H CF3 NMe2
tBu H H H CF3 CO2Me
tBu H H B2 CF3 Me
tBu H H B3 CF3 Me
tBu H H B4 CF3 Me
tBu H H B5 CF3 Me
tBu H H B6 CF3 Me
tBu H H B7 CF3 Me
tBu Cl H B7 CF3 Me
tBu H H B8 CF3 Me
tBu H H B9 CF3 Me
tBu H H B10 CF3 Me
tBu H H B11 CF3 Me
tBu H H B12 CF3 Me
tBu H H B13 CF3 Me
tBu H H B14 CF3 Me
tBu H H B15 CF3 Me
tBu H H B16 CF3 Me
tBu H H B17 CF3 Me
tBu H H B18 CF3 Me
tBu H H B19 CF3 Me
tBu H H B20 CF3 Me
tBu H H B21 CF3 Me
tBu H H B22 CF3 Me
tBu H H B23 CF3 Me
tBu H H B24 CF3 Me
tBu H H B25 CF3 Me
tBu H H B26 CF3 Me
tBu H H B27 CF3 Me
tBu H H B28 CF3 Me
tBu H H B29 CF3 Me
tBu H H B30 CF3 Me
tBu H H B31 CF3 Me
tBu H H B32 CF3 Me
tBu H H B33 CF3 Me
tBu H H B34 CF3 Me
tBu H H Na CF3 Me
tBu H H K CF3 Me
2-pyridyl H H H Me Me
2-pyridyl H H H Et Me
2-pyridyl H H H Cl Cl
2-pyridyl H H H Cl Me
2-pyridyl H H H Cl CF3
2-pyridyl H H H Me Cl
2-pyridyl H H H Br Me
2-pyridyl H H H Me Br
2-pyridyl H H H Me CF3
2-pyridyl H H H OMe Me
2-pyridyl H H H OCF3 Me
2-pyridyl H H H SMe Me
2-pyridyl H H H CO2Me Me
2-pyridyl H H H CO2Et Me
2-pyridyl H H H CF3 Me
2-pyridyl H H H CF3 H
2-pyridyl H H B3 CF3 Me
2-pyridyl H H B6 CF3 Me
2-pyridyl H H B7 CF3 Me
3-pyridyl H H H CF3 Me
4-pyridyl H H H CF3 Me
2-F—Ph H H H Me Me
2-F—Ph H H H Et Me
2-F—Ph H H H CF3 Me
2-F—Ph H H H CF3 Cl
2-F—Ph H H H CF3 H
2-F—Ph H H B3 CF3 Me
2-F—Ph H H B6 CF3 Me
2-F—Ph H H B7 CF3 Me
3-F—Ph H H H CF3 Me
4-F—Ph H H H CF3 Me
2,3-F2—Ph H H H CF3 Me
2,4-F2—Ph H H H CF3 Me
2,5-F2—Ph H H H CF3 Me
Ph H H H Me Me
Ph H H H Et Me
Ph H H H CF3 Me
Ph H H H CF3 Cl
Ph H H H CF3 H
Ph H H B3 CF3 Me
Ph H H B6 CF3 Me
Ph H H B7 CF3 Me
3,4-F2—Ph H H H CF3 Me
3,5-F2—Ph H H H CF3 Me
2-Cl—Ph H H H Me Me
2-Cl—Ph H H H Et Me
2-Cl—Ph H H H CF3 Me
2-Cl—Ph H H H CF3 Cl
2-Cl—Ph H H H CF3 H
2-Cl—Ph H H B3 CF3 Me
2-Cl—Ph H H B6 CF3 Me
2-Cl—Ph H H B7 CF3 Me
3-Cl—Ph H H H CF3 Me
4-Cl—Ph H H H CF3 Me
2,3-Cl2—Ph H H H CF3 Me
2,4-Cl2—Ph H H H CF3 Me
2,5-Cl2—Ph H H H CF3 Me
2,6-Cl2—Ph H H H Me Me
2,6-Cl2—Ph H H H Et Me
2,6-Cl2—Ph H H H CF3 Me
2,6-Cl2—Ph H H H CF3 Cl
2,6-Cl2—Ph H H H CF3 H
2,6-Cl2—Ph H H B3 CF3 Me
2,6-Cl2—Ph H H B6 CF3 Me
2,6-Cl2—Ph H H B7 CF3 Me
3,4-Cl2—Ph H H H CF3 Me
3,5-Cl2—Ph H H H CF3 Me
2-Me—Ph H H H CF3 Me
2,6-Me2—Ph H H H CF3 Me
2-MeO—Ph H H H CF3 Me
2-CF3O—Ph H H H CF3 Me
2-SMe—Ph H H H CF3 Me
2-SOMe—Ph H H H CF3 Me
2-SO2Me—Ph H H H CF3 Me
2-CF3—Ph H H H CF3 Me
2-NO2—Ph H H H CF3 Me
2-CN—Ph H H H CF3 Me
2-NHMe—Ph H H H CF3 Me
2-NMe2—Ph H H H CF3 Me
4-benzyl-Ph H H H Et Me
4-phenoxy-Ph H H H CF3 Me
2-OH—Ph H H H CF3 Me
2-CO2Me—Ph H H H CF3 Me
2-CO2Et—Ph H H H CF3 Me
H CO2Et Ph H CF3 Me
Me Ph H H CF3 Me
Et Me H H CF3 Me
nPr H H H CF3 Me
iPr H H H Et Me
iPr H H H CF3 Me
nBu H H H Et Me
nBu H H H CF3 Me
iBu H H H Et Me
iBu H H H CF3 Me
iBu H H B7 Et Me
iBu H H B7 CF3 Me
secBu H H H Et Me
secBu H H H CF3 Me
2,2-Me2-propyl H H H CF3 Me
nHex H H H CF3 Me
ethenyl H H H CF3 Me
1-propenyl H H H CF3 Me
ethynyl H H H CF3 Me
1-propynyl H H H CF3 Me
CF3 H H H CF3 Me
CHF2 H H H CF3 Me
C2F5 H H H CF3 Me
2,2-Cl2-cPr H H H Et Me
2,2-Cl2-cPr H H H CF3 Me
cPr H H H Et Me
cPr H H H CF3 Me
1-Me-cPr H H H Et Me
1-Me-cPr H H H CF3 Me
cHex H H H Et Me
cHex H H H CF3 Me
CH2Ph H H H CF3 Me
naphthyl-1 H H H Et Me
naphthyl-1 H H H CF3 Me
naphthyl-2 H H H CF3 Me
CO2Me H H H CF3 Me
CO2Et H H H CF3 Me
2-thienyl H H H CF3 Me
CH2OMe H H H CF3 Me
CH2OEt H H H CF3 Me
COCH3 H H H CF3 Me
COtBu H H H CF3 Me
COPh H H H CF3 Me
TABLE 4
Figure USRE038188-20030715-C00131
Figure USRE038188-20030715-C00132
Figure USRE038188-20030715-C00133
Figure USRE038188-20030715-C00134
Figure USRE038188-20030715-C00135
Figure USRE038188-20030715-C00136
Figure USRE038188-20030715-C00137
Figure USRE038188-20030715-C00138
Figure USRE038188-20030715-C00139
Figure USRE038188-20030715-C00140
Figure USRE038188-20030715-C00141
Figure USRE038188-20030715-C00142
Figure USRE038188-20030715-C00143
Figure USRE038188-20030715-C00144
Figure USRE038188-20030715-C00145
Figure USRE038188-20030715-C00146
Figure USRE038188-20030715-C00147
Figure USRE038188-20030715-C00148
Figure USRE038188-20030715-C00149
Figure USRE038188-20030715-C00150
Figure USRE038188-20030715-C00151
Figure USRE038188-20030715-C00152
Figure USRE038188-20030715-C00153
Figure USRE038188-20030715-C00154
Figure USRE038188-20030715-C00155
Figure USRE038188-20030715-C00156
Figure USRE038188-20030715-C00157
Figure USRE038188-20030715-C00158
Figure USRE038188-20030715-C00159
Figure USRE038188-20030715-C00160
Figure USRE038188-20030715-C00161
Figure USRE038188-20030715-C00162
Figure USRE038188-20030715-C00163
Figure USRE038188-20030715-C00164
Figure USRE038188-20030715-C00165
Figure USRE038188-20030715-C00166
Figure USRE038188-20030715-C00167
Figure USRE038188-20030715-C00168
Figure USRE038188-20030715-C00169
Figure USRE038188-20030715-C00170
Figure USRE038188-20030715-C00171
Figure USRE038188-20030715-C00172
Figure USRE038188-20030715-C00173
Figure USRE038188-20030715-C00174
Figure USRE038188-20030715-C00175
Figure USRE038188-20030715-C00176
Figure USRE038188-20030715-C00177
Figure USRE038188-20030715-C00178
Figure USRE038188-20030715-C00179
Figure USRE038188-20030715-C00180
Figure USRE038188-20030715-C00181
Figure USRE038188-20030715-C00182
Figure USRE038188-20030715-C00183
Figure USRE038188-20030715-C00184
Figure USRE038188-20030715-C00185
Figure USRE038188-20030715-C00186
R1 R2 B Y1 Y2 Y3
2,6-F2—Ph H H H CF3 Me
2,6-F2—Ph H H Me H Me
2,6-F2—Ph H H Me H CF3
2,6-F2—Ph H B7 Me H H
2,6-F2—Ph H H Me Me Me
2,6-F2—Ph H H Me Cl Me
2,6-F2—Ph H H Me Br Me
2,6-F2—Ph H H Et Me Me
2,6-F2—Ph H H Cl Me Me
2,6-F2—Ph H H Cl H Me
2,6-F2—Ph H H Cl H CF3
2,6-F2—Ph H H Cl H H
2,6-F2—Ph H H Cl Cl Me
2,6-F2—Ph H H Cl Cl CF3
2,6-F2—Ph H H Cl Cl CF2OMe
2,6-F2—Ph H H Cl Cl COMe
2,6-F2—Ph H H Cl Cl Me
2,6-F2—Ph H H Cl CF3 Me
2,6-F2—Ph H H Br Me Me
2,6-F2—Ph H H Me OMe H
2,6-F2—Ph H B7 OMe H H
2,6-F2—Ph H B7 OCF3 H H
2,6-F2—Ph H B7 SMe H Me
2,6-F2—Ph H H CF3 Me Me
2,6-F2—Ph H H CF3 Cl CF3
2,6-F2—Ph H H CF3 Cl CF2H
2,6-F2—Ph H H CF3 Cl CH2OMe
2,6-F2—Ph H H CF3 Cl Me
2,6-F2—Ph H H CF3 H Me
2,6-F2—Ph H H CF3 Br Me
2,6-F2—Ph H H CF3 NO2 Me
2,6-F2—Ph H H CF3 CN Me
2,6-F2—Ph H H CF3 NHMe Me
2,6-F2—Ph H H CF3 NMe Me
2,6-F2—Ph H H CF3 CO2Me Me
2,6-F2—Ph H H CF3 OMe CF2H
2,6-F2—Ph H H CF3 OCF2H Me
2,6-F2—Ph H H Cl NO2 Me
2,6-F2—Ph H H Cl CN Me
2,6-F2—Ph H H CO2Me Me Me
2,6-F2—Ph H B1 Cl Cl Me
2,6-F2—Ph H B3 Cl Cl Me
2,6-F2—Ph H B6 Cl Cl Me
2,6-F2—Ph H B7 Cl Cl Me
2,6-F2—Ph H B2 CF3 Cl Me
2,6-F2—Ph H B3 CF3 Cl Me
2,6-F2—Ph H B4 CF3 Cl Me
2,6-F2—Ph H B5 CF3 Cl Me
2,6-F2—Ph H B6 CF3 Cl Me
2,6-F2—Ph H B7 CF3 Cl Me
2,6-F2—Ph H B8 CF3 Cl Me
2,6-F2—Ph H B9 CF3 Cl Me
2,6-F2—Ph H B10 CF3 Cl Me
2,6-F2—Ph H B11 CF3 Cl Me
2,6-F2—Ph H B12 CF3 Cl Me
2,6-F2—Ph H B13 CF3 Cl Me
2,6-F2—Ph H B14 CF3 Cl Me
2,6-F2—Ph H B15 CF3 Cl Me
2,6-F2—Ph H B16 CF3 Cl Me
2,6-F2—Ph H B17 CF3 Cl Me
2,6-F2—Ph H B18 CF3 Cl Me
2,6-F2—Ph H B19 CF3 Cl Me
2,6-F2—Ph H B20 CF3 Cl Me
2,6-F2—Ph H B21 CF3 Cl Me
2,6-F2—Ph H B22 CF3 Cl Me
2,6-F2—Ph H B23 CF3 Cl Me
2,6-F2—Ph H B24 CF3 Cl Me
2,6-F2—Ph H B25 CF3 Cl Me
2,6-F2—Ph H B26 CF3 Cl Me
2,6-F2—Ph H B27 CF3 Cl Me
2,6-F2—Ph H B28 CF3 Cl Me
2,6-F2—Ph H B29 CF3 Cl Me
2,6-F2—Ph H B30 CF3 Cl Me
2,6-F2—Ph H B31 CF3 Cl Me
2,6-F2—Ph H B32 CF3 Cl Me
2,6-F2—Ph H B33 CF3 Cl Me
2,6-F2—Ph H B34 CF3 Cl Me
2,6-F2—Ph H Na CF3 Cl Me
2,6-F2—Ph H K CF3 Cl Me
2,6-F2—Ph H B7 Cl H H
2,6-F2—Ph H B9 Cl H H
2,6-F2—Ph H B10 Cl H H
2,6-F2—Ph H B11 Cl H H
tBu H H H CF3 Me
tBu H H Me H Me
tBu H H Me H CF3
tBu H B7 Me H H
tBu H H Me Me Me
tBu H H Me Cl Me
tBu H H Me Br Me
tBu H H Et Me Me
tBu H H Cl Me Me
tBu H H Cl H Me
tBu H H Cl H CF3
tBu H H Cl H H
tBu Me H Cl H H
tBu Cl H Cl H H
tBu H H Cl Cl Me
tBu H H Cl Cl CF3
tBu H H Cl Cl CF2H
tBu H H Cl Cl CH2OMe
tBu H H Cl Cl COMe
tBu H H Cl CF3 Me
tBu H H Br Me Me
tBu H H Me OMe Me
tBu H B7 OMe H H
tBu H B7 OC3 H H
tBu H B7 SMe H H
tBu H H CF3 Me Me
tBu H H CF3 Cl Me
tBu H H CF3 Cl Me
tBu H H CF3 Cl Me
tBu Br H CF3 Cl Me
tBu CF3 H CF3 Cl Me
tBu NO2 H CF3 Cl Me
tBu CN H CF3 Cl Me
tBu CO2Me H CF3 Cl CF3
tBu CO2Et H CF3 Cl CF2H
tBu H H CF3 Cl CH2OMe
tBu H H CF3 H Me
tBu H H CF3 Br Me
tBu H H CF3 NO2 Me
tBu H H CF3 CN Me
tBu H H CF3 NHMe Me
tBu H H CF3 NMe2 Me
tBu H H CF3 CO2Me Me
tBu H H CF3 OMe Me
tBu H H CF3 OCF2H CF2H
tBu H H Cl NO2 Me
tBu H H Cl CN Me
tBu H H CO2Me Me Me
tBu H B1 Cl Cl Me
tBu H B2 Cl Cl Me
tBu H B3 Cl Cl Me
tBu H B4 Cl Cl Me
tBu H B5 Cl Cl Me
tBu H B6 Cl Cl Me
tBu H B7 Cl Cl Me
tBu H B8 Cl Cl Me
tBu H B9 Cl Cl Me
tBu H B10 Cl Cl Me
tBu H B11 Cl Cl Me
tBu H B12 Cl Cl Me
tBu H B13 Cl Cl Me
tBu H B14 Cl Cl Me
tBu H B15 Cl Cl Me
tBu H B16 Cl Cl Me
tBu H B17 Cl Cl Me
tBu H B18 Cl Cl Me
tBu H B19 Cl Cl Me
tBu H B20 Cl Cl Me
tBu H B21 Cl Cl Me
tBu H B22 Cl Cl Me
tBu H B23 Cl Cl Me
tBu H B24 Cl Cl Me
tBu H B25 Cl Cl Me
tBu H B26 Cl Cl Me
tBu H B27 Cl Cl Me
tBu H B28 Cl Cl Me
tBu H B29 Cl Cl Me
tBu H B30 Cl Cl Me
tBu H B31 Cl Cl Me
tBu H B32 Cl Cl Me
tBu H B33 Cl Cl Me
tBu H B34 Cl Cl Me
tBu H Na Cl Cl Me
tBu H K Cl Cl Me
tBu H B2 CF3 Cl Me
tBu H B3 CF3 Cl Me
tBu H B4 CF3 Cl Me
tBu H B5 CF3 Cl Me
tBu H B6 CF3 Cl Me
tBu H B7 CF3 Cl Me
tBu H B8 CF3 Cl Me
tBu H B9 CF3 Cl Me
tBu H B10 CF3 Cl Me
tBu H B11 CF3 Cl Me
tBu H B12 CF3 Cl Me
tBu H B13 CF3 Cl Me
tBu H B14 CF3 Cl Me
tBu H B15 CF3 Cl Me
tBu H B16 CF3 Cl Me
tBu H B17 CF3 Cl Me
tBu H B18 CF3 Cl Me
tBu H B19 CF3 Cl Me
tBu H B20 CF3 Cl Me
tBu H B21 CF3 Cl Me
tBu H B22 CF3 Cl Me
tBu H B23 CF3 Cl Me
tBu H B24 CF3 Cl Me
tBu H B25 CF3 Cl Me
tBu H B26 CF3 Cl Me
tBu H B27 CF3 Cl Me
tBu H B28 CF3 Cl Me
tBu H B29 CF3 Cl Me
tBu H B30 CF3 Cl Me
tBu H B31 CF3 Cl Me
tBu H B32 CF3 Cl Me
tBu H B33 CF3 Cl Me
tBu H B34 CF3 Cl Me
tBu H Na CF3 Cl Me
tBu H K CF3 Cl Me
tBu H B7 Cl H H
tBu H B8 Cl H H
tBu H B15 Cl H H
tBu H B34 Cl H H
2-pyridyl H H H CF3 Me
2-pyridyl H H Me H Me
2-pyridyl H H Me H CF3
2-pyridyl H B7 Me H H
2-pyridyl H H Me Me Me
2-pyridyl H H Me Cl Me
2-pyridyl H H Me Br Me
2-pyridyl H H Et Me Me
2-pyridyl H H Cl Me Me
2-pyridyl H H Cl H Me
2-pyridyl H H Cl H CF3
2-pyridyl H H Cl H H
2-pyridyl Me H Cl H H
2-pyridyl Cl H Cl H H
2-pyridyl H H Cl Cl Me
2-pyridyl H H Cl Cl CF3
2-pyridyl H H Cl Cl CF2H
2-pyridyl H H Cl Cl CH2OMe
2-pyridyl H H Cl Cl COMe
2-pyridyl H H Cl CF3 Me
2-pyridyl H H Br Me Me
2-pyridyl H H Me OMe Me
2-pyridyl H H Br H H
2-pyridyl H B7 OMe H H
2-pyridyl H B7 OCF3 H H
2-pyridyl H B7 SMe H H
2-pyridyl H B7 NH2 H H
2-pyridyl H B7 NHMe H H
2-pyridyl H B7 NMe2 H H
2-pyridyl H B7 NO2 H H
2-pyridyl H B7 CN H H
2-pyridyl H B7 CO2Me H H
2-pyridyl H H CO2Et H H
2-pyridyl H H CF3 Me Me
2-pyridyl H H CF3 Cl Me
2-pyridyl H H CF3 H Me
2-pyridyl H H CF3 Br Me
2-pyridyl H H CF3 CO2Me Me
2-pyridyl H H Cl NO2 Me
2-pyridyl H H Cl CN Me
2-pyridyl H H CO2Me Me Me
2-pyridyl H B3 Cl Cl Me
2-pyridyl H B6 Cl Cl Me
2-pyridyl H B7 Cl Cl Me
2-pyridyl H B3 CF3 Cl Me
2-pyridyl H B6 CF3 Cl Me
2-pyridyl H B7 CF3 Cl Me
2-pyridyl H B2 Cl H H
2-pyridyl H B3 Cl H H
2-pyridyl H B4 Cl H H
2-pyridyl H B5 Cl H H
2-pyridyl H B6 Cl H H
2-pyridyl H B7 Cl H H
2-pyridyl H B8 Cl H H
2-pyridyl H B9 Cl H H
2-pyridyl H B10 Cl H H
2-pyridyl H B11 Cl H H
2-pyridyl H B12 Cl H H
2-pyridyl H B13 Cl H H
2-pyridyl H B14 Cl H H
2-pyridyl H B15 Cl H H
2-pyridyl H B16 Cl H H
2-pyridyl H B17 Cl H H
2-pyridyl H B18 Cl H H
2-pyridyl H B19 Cl H H
2-pyridyl H B20 Cl H H
2-pyridyl H B21 Cl H H
2-pyridyl H B22 Cl H H
2-pyridyl H B23 Cl H H
2-pyridyl H B24 Cl H H
2-pyridyl H B25 Cl H H
2-pyridyl H B26 Cl H H
2-pyridyl H B27 Cl H H
2-pyridyl H B28 Cl H H
2-pyridyl H B29 Cl H H
2-pyridyl H B30 Cl H H
2-pyridyl H B31 Cl H H
2-pyridyl H B32 Cl H H
2-pyridyl H B33 Cl H H
2-pyridyl H B34 Cl H H
2-pyridyl H Na Cl H H
2-pyridyl H K Cl H H
3-pyridyl H H Cl Cl Me
3-pyridyl H H CF3 Cl Me
3-pyridyl H H Cl H H
4-pyridyl H H Cl Cl Me
4-pyridyl H H CF3 Cl Me
4-pyridyl H H Cl H H
2-F—Ph H H Me Me Me
2-F—Ph H H Me Cl Me
2-F—Ph H H Cl Me Me
2-F—Ph H H Cl H H
2-F—Ph H H Cl Cl Me
2-F—Ph H B7 OMe H H
2-F—Ph H B7 SMe H H
2-F—Ph H B7 CF3 Cl Me
2-F—Ph H B7 CF3 H Me
2-F—Ph H B1 Cl Cl Me
2-F—Ph H B3 Cl Cl Me
2-F—Ph H B6 Cl Cl Me
2-F—Ph H B7 Cl Cl Me
2-F—Ph H B3 CF3 Cl Me
2-F—Ph H B6 CF3 Cl Me
2-F—Ph H B7 CF3 Cl Me
2-F—Ph H B7 Cl H H
3-F—Ph H H Cl Cl Me
4-F—Ph H H Cl Cl Me
2,3-F2—Ph H H Cl Cl Me
2,4-F2—Ph H H Cl Cl Me
2,5-F2—Ph H H Cl Cl Me
Ph H H Me Me Me
Ph H H Me Cl Me
Ph H H Cl Me Me
Ph H H Cl H H
Ph H H Cl Cl Me
Ph H B7 OMe H H
Ph H B7 SMe H H
Ph H H CF3 Cl Me
Ph H H CF3 H Me
Ph H B1 Cl Cl Me
Ph H B3 Cl Cl Me
Ph H B6 Cl Cl Me
Ph H B7 Cl Cl Me
Ph H B3 CF3 Cl Me
Ph H B6 CF3 Cl Me
Ph H B7 CF3 Cl Me
Ph Me B7 CF3 Cl Me
Ph H B7 Cl H H
3,4-F2—Ph H H Cl Cl Me
3,5-F2—Ph H H Cl Cl Me
2-Cl—Ph H H Me Me Me
2-Cl—Ph H H Me Cl Me
2-Cl—Ph H H Cl Me Me
2-Cl—Ph H H Cl H H
2-Cl—Ph H H Cl Cl Me
2-Cl—Ph H H OMe H H
2-Cl—Ph H H SMe H H
2-Cl—Ph H H CF3 Cl Me
2-Cl—Ph H H CF3 H Me
2-Cl—Ph H B1 Cl Cl Me
2-Cl—Ph H B3 Cl Cl Me
2-Cl—Ph H B6 Cl Cl Me
2-Cl—Ph H B7 Cl Cl Me
2-Cl—Ph H B3 CF3 Cl Me
2-Cl—Ph H B6 CF3 Cl Me
2-Cl—Ph H B7 CF3 Cl Me
2-Cl—Ph H B7 Cl H H
3-Cl—Ph H H Cl Cl Me
4-Cl—Ph H H Cl Cl Me
2,3-Cl2—Ph H H Cl Cl Me
2,4-Cl2—Ph H H Cl Cl Me
2,5-Cl2—Ph H H Cl Cl Me
2,6-Cl2—Ph H H Me Me Me
2,6-Cl2—Ph H H Me Cl Me
2,6-Cl2—Ph H H Cl Me Me
2,6-Cl2—Ph H H Cl H H
2,6-Cl2—Ph H H Cl Cl Me
2,6-Cl2—Ph H B7 OMe H H
2,6-Cl2—Ph H B7 SMe H H
2,6-Cl2—Ph H H CF3 Cl Me
2,6-Cl2—Ph H H CF3 H Me
2,6-Cl2—Ph H B1 Cl Cl Me
2,6-Cl2—Ph H B3 Cl Cl Me
2,6-Cl2—Ph H B6 Cl Cl Me
2,6-Cl2—Ph Cl B7 Cl Cl Me
2,6-Cl2—Ph H B7 Cl Cl Me
2,6-Cl2—Ph H B3 CF3 Cl Me
2,6-Cl2—Ph H B6 CF3 Cl Me
2,6-Cl2—Ph Cl B7 CF3 Cl Me
2,6-Cl2—Ph H B7 CF3 Cl Me
2,6-Cl2—Ph H H Cl H H
3,4-Cl2—Ph H H Cl Cl Me
3,5-Cl2—Ph H H Cl Cl Me
2-Me—Ph H H Cl Cl Me
2-Me—Ph H H CF3 Cl Me
2,6-Me2—Ph H H Cl Cl Me
2,6-Me2—Ph H H CF3 Cl Me
2-MeO—Ph H H Cl Cl Me
2-MeO—Ph H H CF3 Cl Me
2-CF3O—Ph H H Cl Cl Me
2-CF3O—Ph H H CF3 Cl Me
2-SMe—Ph H H Cl Cl Me
2-SMe—Ph H H CF3 Cl Me
2-SOMe—Ph H H Cl Cl Me
2-SOMe—Ph H H CF3 Cl Me
2-SO2Me—Ph H H Cl Cl Me
2-SO2Me—Ph H H CF3 Cl Me
2-CF3—Ph H H Cl Cl Me
2-CF3—Ph H H CF3 Cl Me
2-NO2—Ph H H Cl Cl Me
2-NO2—Ph H H CF3 Cl Me
2-CN—Ph H H Cl Cl Me
2-CN—Ph H H CF3 Cl Me
2-NHMe—Ph H H Cl Cl Me
2-NMe2—Ph H H Cl Cl Me
4-benzyl-Ph H H Cl Cl Me
4-phenoxy-Ph H H Cl Cl Me
2-OH—Ph H H Cl Cl Me
2-CO2Me—Ph H H Cl Cl Me
2-CO2Me—Ph H H CF3 Cl Me
2-CO2Et—Ph H H Cl Cl Me
2-CO2Et—Ph H H CF3 Cl Me
H H H Cl Cl Me
Me H H Cl Cl Me
Et H H Cl Cl Me
nPr H H Cl Cl Me
iPr H H Cl Cl Me
iPr H H CF3 Cl Me
nBu H H Cl Cl Me
nBu H H CF3 Cl Me
iBu H H Cl Cl Me
iBu H H CF3 Cl Me
iBu H B7 Cl Cl Me
iBu H B7 CF3 Cl Me
iBu H H Cl H H
secBu H H Cl Cl Me
secBu H H CF3 Cl Me
2,2-Me2-propyl H H Cl Cl Me
nHex H H Cl Cl Me
ethenyl H H Cl Cl Me
1-propenyl H H Cl Cl Me
1-propenyl H H CF3 Cl Me
ethynyl H H Cl Cl Me
1-propynyl H H Cl Cl Me
CF3 H H Cl Cl Me
CF3 H H CF3 Cl Me
CHF2 H H Cl Cl Me
C2F5 H H Cl Cl Me
2,2-Cl2-cPr H H Cl Cl Me
2,2-Cl2-cPr H H CF3 Cl Me
cPr H H Cl Cl Me
cPr H H CF3 Cl Me
1-Me-cPr H H Cl Cl Me
1-Me-cPr H H CF3 Cl Me
cHex H H Cl Cl Me
cHex H H CF3 Cl Me
CH2Ph H H Cl Cl Me
naphthyl-1 H H Cl Cl Me
naphthyl-1 H H CF3 Cl Me
naphthyl-2 H H Cl Cl Me
CO2Me H H Cl Cl Me
CO2Et H H Cl Cl Me
2-thienyl H H Cl Cl Me
2-thienyl H H CF3 Cl Me
CH2OMe H H Cl Cl Me
CH2OEt H H Cl Cl Me
COCH3 H H Cl Cl Me
COtBu H H Cl Cl Me
COPh H H Cl Cl Me
TABLE 5
Figure USRE038188-20030715-C00187
Figure USRE038188-20030715-C00188
Figure USRE038188-20030715-C00189
Figure USRE038188-20030715-C00190
Figure USRE038188-20030715-C00191
Figure USRE038188-20030715-C00192
Figure USRE038188-20030715-C00193
Figure USRE038188-20030715-C00194
Figure USRE038188-20030715-C00195
Figure USRE038188-20030715-C00196
Figure USRE038188-20030715-C00197
Figure USRE038188-20030715-C00198
Figure USRE038188-20030715-C00199
Figure USRE038188-20030715-C00200
Figure USRE038188-20030715-C00201
Figure USRE038188-20030715-C00202
Figure USRE038188-20030715-C00203
Figure USRE038188-20030715-C00204
Figure USRE038188-20030715-C00205
Figure USRE038188-20030715-C00206
Figure USRE038188-20030715-C00207
Figure USRE038188-20030715-C00208
Figure USRE038188-20030715-C00209
Figure USRE038188-20030715-C00210
Figure USRE038188-20030715-C00211
Figure USRE038188-20030715-C00212
Figure USRE038188-20030715-C00213
Figure USRE038188-20030715-C00214
Figure USRE038188-20030715-C00215
Figure USRE038188-20030715-C00216
Figure USRE038188-20030715-C00217
Figure USRE038188-20030715-C00218
Figure USRE038188-20030715-C00219
Figure USRE038188-20030715-C00220
Figure USRE038188-20030715-C00221
Figure USRE038188-20030715-C00222
Figure USRE038188-20030715-C00223
Figure USRE038188-20030715-C00224
Figure USRE038188-20030715-C00225
Figure USRE038188-20030715-C00226
Figure USRE038188-20030715-C00227
Figure USRE038188-20030715-C00228
R1 R2 B Y1 Y2
2,6-F2—Ph H H Me H
2,6-F2—Ph H H Me Me
2,6-F2—Ph H H Et Me
2,6-F2—Ph Me H Et Me
2,6-F2—Ph H H Cl Cl
2,6-F2—Ph H H Cl Me
2,6-F2—Ph H H Cl CF3
2,6-F2—Ph H H Me Cl
2,6-F2—Ph H H Br Me
2,6-F2—Ph H H Me CF3
2,6-F2—Ph H H OMe Me
2,6-F2—Ph H H OCF3 Me
2,6-F2—Ph H H SMe Me
2,6-F2—Ph H H CO2Me Me
2,6-F2—Ph H H CO2Et Me
2,6-F2—Ph H H CF3 Me
2,6-F2—Ph H H CF3 H
2,6-F2—Ph H H CF3 Br
2,6-F2—Ph H H CF3 NO2
2,6-F2—Ph H H CF3 CN
2,6-F2—Ph H H CF3 NHMe
2,6-F2—Ph H H CF3 NMe2
2,6-F2—Ph H H CF3 CO2Me
2,6-F2—Ph H B3 CF3 Me
2,6-F2—Ph H B6 CF3 Me
2,6-F2—Ph H B7 CF3 Me
tBu H H Me Me
tBu H H Et Me
tBu H H Cl Cl
tBu H H Cl Me
tBu H H Me Cl
tBu H H Cl CF3
tBu H H Br Me
tBu H H Me Br
tBu H H Me CF3
tBu H H OMe Me
tBu H H OCF3 Me
tBu H H SMe Me
tBu H H CO2Me Me
tBu H H CO2Et Me
tBu H H CF3 Me
tBu H H CF3 H
tBu H H CF3 Br
tBu H H CF3 NO2
tBu H B2 CF3 Me
tBu H B3 CF3 Me
tBu H B4 CF3 Me
tBu H B5 CF3 Me
tBu H B6 CF3 Me
tBu H B7 CF3 Me
tBu H B8 CF3 Me
tBu H B9 CF3 Me
tBu H B10 CF3 Me
tBu H B11 CF3 Me
tBu H B14 CF3 Me
tBu H B20 CF3 Me
tBu H B23 CF3 Me
tBu H B24 CF3 Me
tBu H B25 CF3 Me
tBu H B26 CF3 Me
tBu H B28 CF3 Me
tBu H B30 CF3 Me
tBu H B31 CF3 Me
tBu H B32 CF3 Me
tBu H B33 CF3 Me
tBu H B34 CF3 Me
tBu H Na CF3 Me
tBu H K CF3 Me
2-pyridyl H H Me Me
2-pyridyl H H Et Me
2-pyridyl H H Cl Cl
2-pyridyl H H Cl Me
2-pyridyl H H Me Cl
2-pyridyl H H Br Me
2-pyridyl H H Me CF3
2-pyridyl H H CO2Me Me
2-pyridyl H H CO2Et Me
2-pyridyl H H CF3 Me
2-pyridyl H H CF3 Br
2-pyridyl H H CF3 NO2
2-pyridyl H H CF3 CN
2-pyridyl H H CF3 NMe2
2-pyridyl H B3 CF3 Me
2-pyridyl H B6 CF3 Me
2-pyridyl H B7 CF3 Me
3-pyridyl H H Et Me
3-pyridyl H H CF3 Me
4-pyridyl H H Et Me
4-pyridyl H H CF3 Me
2-F—Ph H H Me Me
2-F—Ph H H Et Me
2-F—Ph H H CF3 Me
2-F—Ph H H CF3 Cl
2-F—Ph H H CF3 H
2-F—Ph H B3 CF3 Me
2-F—Ph H B6 CF3 Me
2-F—Ph H B7 CF3 Me
3-F—Ph H H Et Me
3-F—Ph H H CF3 Me
4-F—Ph H H Et Me
2,3-F2—Ph H H Et Me
2,4-F2—Ph H H Et Me
2,5-F2—Ph H H Et Me
Ph H H Me Me
Ph H H Et Me
Ph H H CF3 Me
Ph H H CF3 Cl
Ph H H CF3 H
Ph H B3 CF3 Me
Ph H B6 CF3 Me
Ph H B7 CF3 Me
3,4-F2—Ph H H Et Me
3,5-F2—Ph H H Et Me
2-Cl—Ph H R Me Me
2-Cl—Ph H H Et Me
2-Cl—Ph H H CF3 Me
2-Cl—Ph H H CF3 Cl
2-Cl—Ph H H CF3 H
2-Cl—Ph H B3 CF3 Me
2-Cl—Ph H B6 CF3 Me
2-Cl—Ph H B7 CF3 Me
3-Cl—Ph H H CF3 Me
4-Cl—Ph H H CF3 Me
2,3-Cl2—Ph H H CF3 Me
2,4-Cl2—Ph H H CF3 Me
2,5-Cl2—Ph H H CF3 Me
2,6-Cl2—Ph H H Me Me
2,6-Cl2—Ph H H Et Me
2,6-Cl2—Ph H H CF3 Me
2,6-Cl2—Ph H H CF3 Cl
2,6-Cl2—Ph H H CF3 H
2,6-Cl2—Ph H B3 CF3 Me
2,6-Cl2—Ph H B6 CF3 Me
2,6-Cl2—Ph H B7 CF3 Me
3,4-Cl2—Ph H H CF3 Me
3,5-Cl2—Ph H H CF3 Me
2-Me—Ph H H Et Me
2-Me—Ph H H CF3 Me
2,6-Me2—Ph H H Et Me
2,6-Me2—Ph H H CF3 Me
2-MeO—Ph H H Et Me
2-MeO—Ph H H CF3 Me
2-CF3O—Ph H H Et Me
2-CF3O—Ph H H CF3 Me
2-SMe—Ph H H Et Me
2-SMe—Ph H H CF3 Me
2-SOMe—Ph H H Et Me
2-SOMe—Ph H H CF3 Me
2-SO2Me—Ph H H Et Me
2-SO2Me—Ph H H CF3 Me
2-CF3—Ph H H Et Me
2-CF3—Ph H H CF3 Me
2-NO2—Ph H H Et Me
2-NO2—Ph H H CF3 Me
2-CN—Ph H H Et Me
2-NHMe2—Ph H H CF3 Me
2-NMe2—Ph H H Et Me
2-NMe2—Ph H H CF3 Me
4-benzyl-Ph H H CF3 Me
4-phenoxy-Ph H H CF3 Me
2-OH—Ph H H CF3 Me
2-CO2Me—Ph H H Et Me
2-CO2Me—Ph H H CF3 Me
2-CO2Et—Ph H H Et Me
2-CO2Et—Ph H H CF3 Me
H H H CF3 Me
Me H H CF3 Me
Et H H CF3 Me
nPr H H CF3 Me
iPr H H Et Me
iPr H H CF3 Me
nBu H H Et Me
nBu H H CF3 Me
iBu H H Et Me
iBu H H CF3 Me
iBu H B7 Et Me
iBu H B7 CF3 Me
secBu H H Et Me
secBu H H CF3 Me
2,2-Me2-propyl H H CF3 Me
nHex H H CF3 Me
ethenyl H H CF3 Me
1-propenyl H H Et Me
1-propenyl H H CF3 Me
ethynyl H H CF3 Me
1-propynyl H H CF3 Me
CF3 H H Et Me
CF3 H H CF3 Me
CHF2 H H Et Me
C2F5 H H Et Me
2,2-Cl2-cPr H H Et Me
2,2-Cl2-cPr H H CF3 Me
cPr H H Et Me
cPr H H CF3 Me
1-Me-cPr H H Et Me
1-Me-cPr H H CF3 Me
cHex H H Et Me
cHex H H CF3 Me
CH2Ph H H CF3 Me
1-naphthyl H H Et Me
1-naphthyl H H CF3 Me
2-naphthyl H H CF3 Me
CO2Me H H CF3 Me
CO2Et H H CF3 Me
2-thienyl H H CF3 Me
TABLE 6
Figure USRE038188-20030715-C00229
Figure USRE038188-20030715-C00230
Figure USRE038188-20030715-C00231
Figure USRE038188-20030715-C00232
Figure USRE038188-20030715-C00233
Figure USRE038188-20030715-C00234
Figure USRE038188-20030715-C00235
Figure USRE038188-20030715-C00236
Figure USRE038188-20030715-C00237
Figure USRE038188-20030715-C00238
Figure USRE038188-20030715-C00239
R1 R2 B Y1 Y2 Y3
2,6-F2—Ph H B7 H CF3 Me
2,6-F2—Ph H B7 Me H Me
2,6-F2—Ph H B7 Me H CF3
2,6-F2—Ph H B7 Me H H
2,6-F2—Ph H B7 Me Me Me
2,6-F2—Ph H B7 Me Cl Me
2,6-F2—Ph H B7 Me Br Me
2,6-F2—Ph H B7 Et Me Me
2,6-F2—Ph H B7 Cl Me Me
2,6-F2—Ph H B7 Cl H Me
2,6-F2—Ph H B7 Cl H CF3
2,6-F2—Ph H B7 Cl H H
2,6-F2—Ph H B7 Cl Cl CF3
2,6-F2—Ph H B7 Cl Cl CF2H
2,6-F2—Ph H B7 Cl Cl CH2OMe
2,6-F2—Ph H B7 Cl Cl COMe
2,6-F2—Ph H B7 Cl CF3 Me
2,6-F2—Ph H B7 Br Me Me
2,6-F2—Ph H B7 Me OMe Me
2,6-F2—Ph H B7 OMe H H
2,6-F2—Ph H B7 OCF3 H H
2,6-F2—Ph H B7 SMe H H
2,6-F2—Ph H B7 CF3 Me Me
2,6-F2—Ph H B7 CF3 Cl CF3
2,6-F2—Ph H B7 CF3 Cl CF2H
2,6-F2—Ph H B7 CF3 Cl CH2OMe
2,6-F2—Ph H B7 CF3 H Me
2,6-F2—Ph H B7 CF3 Br Me
2,6-F2—Ph H B7 CF3 NO2 Me
2,6-F2—Ph H B7 CF3 CN Me
2,6-F2—Ph H B7 CF3 NHMe Me
2,6-F2—Ph H B7 CF3 NMe2 Me
2,6-F2—Ph H B7 CF3 CO2Me Me
2,6-F2—Ph H B7 CF3 OMe Me
2,6-F2—Ph H B7 CF3 OCF2H CF2H
2,6-F2—Ph H B7 Cl NO2 Me
2,6-F2—Ph H B7 Cl CN Me
2,6-F2—Ph H B7 CO2Me Me Me
2,6-F2—Ph H B1 Cl Cl Me
2,6-F2—Ph Me B1 Cl Cl Me
2,6-F2—Ph H B3 Cl Cl Me
2,6-F2—Ph H B4 Cl Cl Me
2,6-F2—Ph H B5 Cl Cl Me
2,6-F2—Ph H B6 Cl Cl Me
2,6-F2—Ph H B7 Cl Cl Me
2,6-F2—Ph Me B7 Cl Cl Me
2,6-F2—Ph H B2 CF3 Cl Me
2,6-F2—Ph H B3 CF3 Cl Me
2,6-F2—Ph H B4 CF3 Cl Me
2,6-F2—Ph H B5 CF3 Cl Me
2,6-F2—Ph H B6 CF3 Cl Me
2,6-F2—Ph H B7 CF3 Cl Me
2,6-F2—Ph Me B7 CF3 Cl Me
2,6-F2—Ph H B8 CF3 Cl Me
2,6-F2—Ph H B9 CF3 Cl Me
2,6-F2—Ph H B10 CF3 Cl Me
2,6-F2—Ph H B11 CF3 Cl Me
2,6-F2—Ph H B12 CF3 Cl Me
2,6-F2—Ph H B13 CF3 Cl Me
2,6-F2—Ph H B14 CF3 Cl Me
2,6-F2—Ph H B15 CF3 Cl Me
2,6-F2—Ph H B16 CF3 Cl Me
2,6-F2—Ph H B17 CF3 Cl Me
2,6-F2—Ph H B18 CF3 Cl Me
2,6-F2—Ph H B19 CF3 Cl Me
2,6-F2—Ph H B20 CF3 Cl Me
2,6-F2—Ph H B21 CF3 Cl Me
2,6-F2—Ph H B22 CF3 Cl Me
2,6-F2—Ph H B23 CF3 Cl Me
2,6-F2—Ph H B24 CF3 Cl Me
2,6-F2—Ph H B25 CF3 Cl Me
2,6-F2—Ph H B26 CF3 Cl Me
2,6-F2—Ph H B27 CF3 Cl Me
2,6-F2—Ph H B28 CF3 Cl Me
2,6-F2—Ph H B29 CF3 Cl Me
2,6-F2—Ph H B30 CF3 Cl Me
2,6-F2—Ph H B31 CF3 Cl Me
2,6-F2—Ph H B32 CF3 Cl Me
2,6-F2—Ph H B33 CF3 Cl Me
2,6-F2—Ph H B34 CF3 Cl Me
2,6-F2—Ph H B7 Cl H H
2,6-F2—Ph H B9 Cl H H
2,6-F2—Ph H B10 Cl H H
2,6-F2—Ph H B11 Cl H H
2,6-F2—Ph H B45 CF3 Cl Me
2,6-F2—Ph H B46 CF3 Cl Me
tBu H B7 H CF3 Me
tBu H B7 Me H Me
tBu H B7 Me H CF3
tBu H B7 Me H H
tBu H B7 Me Me Me
tBu H B7 Me Cl Me
tBu H B7 Me Br Me
tBu H B7 Et Me Me
tBu H B7 Cl Me Me
tBu H B7 Cl H Me
tBu H B7 Cl H CF3
tBu H B7 Cl H H
tBu H B7 Cl Cl CF3
tBu H B7 Cl Cl CF2H
tBu H B7 Cl Cl CH2OMe
tBu H B7 Cl Cl COMe
tBu H B7 Cl CF3 Me
tBu H B7 Br Me Me
tBu H B7 Me OMe Me
tBu H B7 OMe H H
tBu H B7 OCF3 H H
tBu H B7 SMe H H
tBu H B7 CF3 Me Me
tBu Br B7 CF3 Cl Me
tBu Me B7 CF3 Cl Me
tBu CF3 B7 CF3 Cl Me
tBu NO2 B7 CF3 Cl Me
tBu CN B7 CF3 Cl Me
tBu CO2Me B7 CF3 Cl Me
tBu CO2Et B7 CF3 Cl Me
tBu H B7 CF3 Cl CF3
tBu H B7 CF3 Cl CF2H
tBu H B7 CF3 Cl CH2OMe
tBu H B7 CF3 H Me
tBu H B7 CF3 Br Me
tBu H B7 CF3 NO2 Me
tBu H B7 CF3 CN Me
tBu H B7 CF3 NHMe Me
tBu H B7 CF3 NMe2 Me
tBu H B7 CF3 CO2Me Me
tBu H B7 CF3 OMe Me
tBu H B7 CF3 OCF2H CF2H
tBu H B7 Cl NO2 Me
tBu H B7 Cl CN Me
tBu H B7 CO2Me Me Me
tBu H B1 Cl Cl Me
tBu H B2 Cl Cl Me
tBu H B3 Cl Cl Me
tBu H B4 Cl Cl Me
tBu H B5 Cl Cl Me
tBu H B6 Cl Cl Me
tBu H B7 Cl Cl Me
tBu Me B7 Cl Cl Me
tBu H B8 Cl Cl Me
tBu H B9 Cl Cl Me
tBu H B10 Cl Cl Me
tBu H B11 Cl Cl Me
tBu H B12 Cl Cl Me
tBu H B13 Cl Cl Me
tBu H B14 Cl Cl Me
tBu H B15 Cl Cl Me
tBu H B16 Cl Cl Me
tBu H B17 Cl Cl Me
tBu H B18 Cl Cl Me
tBu H B19 Cl Cl Me
tBu H B20 Cl Cl Me
tBu H B21 Cl Cl Me
tBu H B22 Cl Cl Me
tBu H B23 Cl Cl Me
tBu H B24 Cl Cl Me
tBu H B25 Cl Cl Me
tBu H B26 Cl Cl Me
tBu H B27 Cl Cl Me
tBu H B28 Cl Cl Me
tBu H B29 Cl Cl Me
tBu H B30 Cl Cl Me
tBu H B31 Cl Cl Me
tBu H B32 Cl Cl Me
tBu H B33 Cl Cl Me
tBu H B34 Cl Cl Me
tBu H B45 Cl Cl Me
tBu H B46 Cl Cl Me
tBu H B2 CF3 Cl Me
tBu H B3 CF3 Cl Me
tBu H B4 CF3 Cl Me
tBu H B5 CF3 Cl Me
tBu H B6 CF3 Cl Me
tBu H B7 CF3 Cl Me
tBu H B8 CF3 Cl Me
tBu H B9 CF3 Cl Me
tBu H B10 CF3 Cl Me
tBu H B11 CF3 Cl Me
tBu H B12 CF3 Cl Me
tBu H B13 CF3 Cl Me
tBu H B14 CF3 Cl Me
tBu H B15 CF3 Cl Me
tBu H B16 CF3 Cl Me
tBu H B17 CF3 Cl Me
tBu H B18 CF3 Cl Me
tBu H B19 CF3 Cl Me
tBu H B20 CF3 Cl Me
tBu H B21 CF3 Cl Me
tBu H B22 CF3 Cl Me
tBu H B23 CF3 Cl Me
tBu H B24 CF3 Cl Me
tBu H B25 CF3 Cl Me
tBu H B26 CF3 Cl Me
tBu H B27 CF3 Cl Me
tBu H B28 CF3 Cl Me
tBu H B29 CF3 Cl Me
tBu H B30 CF3 Cl Me
tBu H B31 CF3 Cl Me
tBu H B32 CF3 Cl Me
tBu H B33 CF3 Cl Me
tBu H B34 CF3 Cl Me
tBu H B35 CF3 Cl Me
tBu H B43 CF3 Cl Me
tBu H B7 Cl H H
tBu H B9 Cl H H
tBu H B10 Cl H H
tBu H B11 Cl H H
2-pyridyl H B7 H CF3 Me
2-pyridyl H B7 Me H Me
2-pyridyl H B7 Me H CF3
2-pyridyl H B7 Me H H
2-pyridyl H B7 Me Me Me
2-pyridyl H B7 Me Cl Me
2-pyridyl H B7 Cl H Me
2-pyridyl H B7 Cl H CF3
2-pyridyl H B7 OMe H H
2-pyridyl H B7 OCF3 H H
2-pyridyl H B7 SMe H H
2-pyridyl H B7 NO2 H H
2-pyridyl H B7 CO2Me H H
2-pyridyl H B7 CO2Et H H
2-pyridyl H B7 CF3 Me Me
2-pyridyl H B7 CF3 H Me
2-pyridyl H B7 CF3 Br Me
2-pyridyl H B3 Cl Cl Me
2-pyridyl H B7 Cl Cl Me
2-pyridyl H B3 CF3 Cl Me
2-pyridyl H B7 CF3 Cl Me
2-pyridyl H B3 Cl H H
2-pyridyl H B4 Cl H H
2-pyridyl H B5 Cl H H
2-pyridyl H B6 Cl H H
2-pyridyl H B7 Cl H H
2-pyridyl H B8 Cl H H
2-pyridyl H B9 Cl H H
2-pyridyl H B10 Cl H H
2-pyridyl H B11 Cl H H
2-pyridyl H B20 Cl H H
2-pyridyl H B24 Cl H H
2-pyridyl H B25 Cl H H
2-pyridyl H B26 Cl H H
2-pyridyl H B28 Cl H H
2-pyridyl H B30 Cl H H
2-pyridyl H B31 Cl H H
2-pyridyl H B32 Cl H H
2-pyridyl H B33 Cl H H
2-pyridyl H B43 Cl H H
2-pyridyl H B46 Cl H H
3-pyridyl H B7 Cl Cl Me
3-pyridyl H B7 Cl H H
4-pyridyl H B7 Cl Cl Me
4-pyridyl H B7 Cl H H
2-F—Ph H B7 Me Me Me
2-F—Ph H B7 Me Cl Me
2-F—Ph H B7 Cl Me Me
2-F—Ph H B7 Cl H H
2-F—Ph H B7 OMe H H
2-F—Ph H B7 SMe H H
2-F—Ph H B7 CF3 H Me
2-F—Ph H B1 Cl Cl Me
2-F—Ph H B3 Cl Cl Me
2-F—Ph H B6 Cl Cl Me
2-F—Ph H B7 Cl Cl Me
2-F—Ph H B3 CF3 Cl Me
2-F—Ph H B6 CF3 Cl Me
2-F—Ph H B7 CF3 Cl Me
2-F—Ph H B7 Cl H H
3-F—Ph H B7 Cl Cl Me
4-F—Ph H B7 Cl Cl Me
2,3-F2—Ph H B7 CF3 Cl Me
2,4-F2—Ph H B7 Cl Cl Me
2,5-F2—Ph H B7 Cl Cl Me
Ph H B7 Me Me Me
Ph H B7 Me Cl Me
Ph H B7 Cl Me Me
Ph H B7 Cl H H
Ph H B7 OMe H H
Ph H B7 SMe H H
Ph H B7 CF3 H Me
Ph H B1 Cl Cl Me
Ph H B3 Cl Cl Me
Ph H B6 Cl Cl Me
Ph H B7 Cl Cl Me
Ph H B3 CF3 Cl Me
Ph H B6 CF3 Cl Me
Ph H B7 CF3 Cl Me
Ph Me B7 CF3 Cl Me
Ph H B7 Cl H H
3,4-F2—Ph H B7 Cl Cl Me
3,5-F2—Ph H B7 Cl Cl Me
2-Cl—Ph H B7 Me Me Me
2-Cl—Ph H B7 Me Cl Me
2-Cl—Ph H B7 Cl Me Me
2-Cl—Ph H B7 Cl H H
2-Cl—Ph H B7 OMe H H
2-Cl—Ph H B7 SMe H H
2-Cl—Ph H B7 CF3 H Me
2-Cl—Ph H B6 Cl Cl Me
2-Cl—Ph H B7 Cl Cl Me
2-Cl—Ph H B3 CF3 Cl Me
2-Cl—Ph H B6 CF3 Cl Me
2-Cl—Ph H B7 CF3 Cl Me
2-Cl—Ph H B7 Cl H H
3-Cl—Ph H B7 Cl Cl Me
4-Cl—Ph H B7 Cl Cl Me
2,3-Cl2—Ph H B7 Cl Cl Me
2,4-Cl2—Ph H B7 Cl Cl Me
2,5-Cl2—Ph H B7 Cl Cl Me
2,6-Cl2—Ph H B7 Me Me Me
2,6-Cl2—Ph H B7 Me Cl Me
2,6-Cl2—Ph H B7 Cl Me Me
2,6-Cl2—Ph H B7 Cl H H
2,6-Cl2—Ph H B7 OMe H H
2,6-Cl2—Ph H B7 SMe H H
2,6-Cl2—Ph H B7 CF3 H Me
2,6-Cl2—Ph H B1 Cl Cl Me
2,6-Cl2—Ph H B3 Cl Cl Me
2,6-Cl2—Ph H B6 Cl Cl Me
2,6-Cl2—Ph H B7 Cl Cl Me
2,6-Cl2—Ph Me B7 Cl Cl Me
2,6-Cl2—Ph H B3 CF3 Cl Me
2,6-Cl2—Ph H B6 CF3 Cl Me
2,6-Cl2—Ph H B7 CF3 Cl Me
2,6-Cl2—Ph Me B7 CF3 Cl Me
3,4-Cl2—Ph H B7 Cl Cl Me
3,5-Cl2—Ph H B7 Cl Cl Me
2-Me—Ph H B7 Cl Cl Me
2-Me—Ph H B7 CF3 Cl Me
2,6-Me2—Ph H B7 Cl Cl Me
2,6-Me2—Ph H B7 CF3 Cl Me
2-MeO—Ph H B7 Cl Cl Me
2-MeO—Ph H B7 CF3 Cl Me
2-CF3O—Ph H B7 Cl Cl Me
2-CF3O—Ph H B7 CF3 Cl Me
2-SMe—Ph H B7 Cl Cl Me
2-SOMe—Ph H B7 Cl Cl Me
2-SO2Me—Ph H B7 Cl Cl Me
2-CF3—Ph H B7 Cl Cl Me
2-NO2—Ph H B7 Cl Cl Me
2-NO2—Ph H B9 Cl Cl Me
2-CN—Ph H B7 Cl Cl Me
2-NHMe—Ph H B7 Cl Cl Me
2-NMe2—Ph H B7 Cl Cl Me
4-benzyl-Ph H B7 Cl Cl Me
4-phenoxy-Ph H B7 Cl Cl Me
4-tBu—Ph H B1 Cl H Me
2-OH—Ph H B7 Cl Cl Me
2-CO2Me—Ph H B7 Cl Cl Me
2-CO2Et—Ph H B7 Cl Cl Me
H H B7 Cl Cl Me
Me H B7 Cl Cl Me
Et H B7 Cl Cl Me
nPr H B7 Cl Cl Me
iPr H B7 Cl Cl Me
iPr H B7 CF3 Cl Me
nBu H B7 Cl Cl Me
nBu H B7 CF3 Cl Me
iBu H B7 Cl Cl Me
iBu H B7 CF3 Cl Me
iBu Me B7 Cl Cl Me
iBu Me B7 CF3 Cl Me
iBu H B7 Cl H H
secBu H B7 Cl Cl Me
secBu H B7 CF3 Cl Me
pentyl-2 H B1 Cl Cl Me
2,2-Me2-propyl H B7 Cl Cl Me
nHex H B7 Cl Cl Me
ethenyl H B7 Cl Cl Me
1-propenyl H B7 Cl Cl Me
1-propenyl H B7 CF3 Cl Me
ethynyl H B7 Cl Cl Me
1-propynyl H B7 Cl Cl Me
CF3 H B7 Cl Cl Me
CHF2 H B7 Cl Cl Me
C2F5 H B7 Cl Cl Me
2,2-Cl2-cPr H B7 Cl Cl Me
2,2-Cl2-cPr H B7 CF3 Cl Me
cPr H B7 Cl Cl Me
cPr H B7 CF3 Cl Me
1-Me-cPr H B7 Cl Cl Me
1-Me-cPr H B7 CF3 Cl Me
cHex H B7 Cl Cl Me
cHex H B7 CF3 Cl Me
CH2Ph H B7 Cl Cl Me
naphthyl-1 H B7 Cl Cl Me
naphthyl-1 H B7 CF3 Cl Me
naphthyl-2 H B9 Cl H H
naphthyl-2 H B7 Cl Cl Me
CO2Me H B7 Cl Cl Me
CO2Et H B7 Cl Cl Me
2-thienyl H B7 Cl Cl Me
2-thienyl H B7 CF3 Cl Me
CH2OMe H B7 Cl Cl Me
CH2OEt H B7 Cl Cl Me
COCH3 H B7 Cl Cl Me
COtBu H B7 Cl Cl Me
COPh H B7 Cl Cl Me
TABLE 7
Figure USRE038188-20030715-C00240
Figure USRE038188-20030715-C00241
Figure USRE038188-20030715-C00242
Figure USRE038188-20030715-C00243
Figure USRE038188-20030715-C00244
Figure USRE038188-20030715-C00245
Figure USRE038188-20030715-C00246
Figure USRE038188-20030715-C00247
Figure USRE038188-20030715-C00248
Figure USRE038188-20030715-C00249
Figure USRE038188-20030715-C00250
Figure USRE038188-20030715-C00251
Figure USRE038188-20030715-C00252
R1 R2 B Y1 Y2
Ph H B7 Me H
Ph H B7 Me Me
Ph H B7 Et Me
Ph Me B7 Et Me
Ph H B7 Me Cl
Ph H B7 Cl Me
Ph H B7 Br Me
Ph H B7 Me Br
Ph H B7 Me CF3
Ph H B7 CF3 H
Ph H B7 CF3 Br
Ph H B7 CF3 NO2
Ph H B7 CF3 CN
Ph H B4 CF3 Me
Ph H B7 CF3 Me
Ph H B9 CF3 Me
tBu H B7 Me Me
tBu H B7 Et Me
tBu H B7 Cl Cl
tBu H B7 Cl Me
tBu H B7 Me Cl
tBu H B7 Cl CF3
tBu H B7 Br Me
tBu H B7 Me Br
tBu H B7 Me CF3
tBu H B7 CF3 Me
tBu H B7 CF3 H
tBu H B7 CF3 Br
tBu H B7 CF3 NO2
tBu H B7 CF3 CN
tBu H B4 CF3 Me
tBu H B5 CF3 Me
tBu H B6 CF3 Me
tBu H B7 CF3 Me
tBu H B9 CF3 Me
tBu H B20 CF3 Me
tBu H B24 CF3 Me
tBu H B25 CF3 Me
tBu H B26 CF3 Me
2-pyridyl H B7 Me Me
2-pyridyl H B7 Et Me
2-pyridyl H B7 Cl Cl
2-pyridyl H B7 Cl Me
2-pyridyl H B7 Cl CF3
2-pyridyl H B7 Me Cl
2-pyridyl H B7 Br Me
2-thienyl H B7 Me CF3
2-pyridyl H B7 CF3 H
2-pyridyl H B7 CF3 Br
2-pyridyl H B7 CF3 Me
3-pyridyl H B7 Et Me
4-pyridyl H B7 CF3 Me
2-F—Ph H B7 Me Me
2-F—Ph H B7 Et Me
2-F—Ph H B7 CF3 Cl
2-F—Ph H B7 CF3 H
2-F—Ph H B4 CF3 Me
2-F—Ph H B7 CF3 Me
2-F—Ph H B9 CF3 Me
3-F—Ph H B7 Et Me
4-F—Ph H B7 Et Me
2,3-F2—Ph H B7 Et Me
2,4-F2—Ph H B7 Et Me
2,5-F2—Ph H B7 Et Me
2,6-F2—Ph H B7 Me Me
2,6-F2—Ph H B7 Et Me
2,6-F2—Ph H B7 CF3 Cl
2,6-F2—Ph H B7 CF3 H
2,6-F2—Ph H B4 CF3 Me
2,6-F2—Ph H B7 CF3 Me
2,6-F2—Ph H B9 CF3 Me
3,4-F2—Ph H B7 Et Me
3,5-F2—Ph H B7 Et Me
2-Cl—Ph H B7 Me Me
2-Cl—Ph H B7 Et Me
2-Cl—Ph H B7 CF3 Cl
2-Cl—Ph H B7 CF3 H
2-Cl—Ph H B4 CF3 Me
2-Cl—Ph H B7 CF3 Me
2-Cl—Ph H B9 CF3 Me
3-Cl—Ph H B7 CF3 Me
4-Cl—Ph H B7 CF3 Me
2,3-Cl2—Ph H B7 CF3 Me
2,4-Cl2—Ph H B7 CF3 Me
2,5-Cl2—Ph H B7 CF3 Me
2,6-Cl2—Ph H B7 Me Me
2,6-Cl2—Ph H B7 Et Me
2,6-Cl2—Ph H B7 CF3 Cl
2,6-Cl2—Ph H B7 CF3 H
2,6-Cl2—Ph H B4 CF3 Me
2,6-Cl2—Ph H B7 CF3 Me
2,6-Cl2—Ph H B9 CF3 Me
3,4-Cl2—Ph H B7 CF3 Me
3,5-Cl2—Ph H B7 CF3 Me
2-Me—Ph H B7 Et Me
2-Me—Ph H B7 CF3 Me
2,6-Me2—Ph H B7 Et Me
2,6-Me2—Ph H B7 CF3 Me
2-MeO—Ph H B7 Et Me
2-MeO—Ph H B7 CF3 Me
2-CF3O—Ph H B7 CF3 Me
2-SMe—Ph H B7 CF3 Me
2-SOMe—Ph H B7 CF3 Me
2-SO2Me—Ph H B7 CF3 Me
2-CF3—Ph H B7 CF3 Me
2-NO2—Ph H B7 CF3 Me
2-CN—Ph H B7 CF3 Me
2-NMe2—Ph H B7 CF3 Me
4-benzyl-Ph H B7 CF3 Me
4-phenoxy-Ph H B7 CF3 Me
2-OH—Ph H B7 CF3 Me
2-CO2Me—Ph H B7 Et Me
2-CO2Me—Ph H B7 CF3 Me
2-CO2Et—Ph H B7 Et Me
2-CO2Et—Ph H B7 CF3 Me
H H B7 CF3 Me
Me H B7 CF3 Me
Et H B7 CF3 Me
nPr H B7 CF3 Me
iPr H B7 Et Me
iPr H B7 CF3 Me
nBu H B7 Et Me
nBu H B7 CF3 Me
iBu H B7 Et Me
iBu H B7 CF3 Me
secBu H B7 Et Me
secBu H B7 CF3 Me
2,2-Me2-propyl H B7 CF3 Me
nHex H B7 CF3 Me
ethenyl H B7 CF3 Me
1-propenyl H B7 Et Me
1-propenyl H B7 CF3 Me
ethynyl H B7 CF3 Me
1-propynyl H B7 CF3 Me
CF3 H B7 Et Me
CHF2 H B7 CF3 Me
C2F5 H B7 CF3 Me
2,2-Cl2-cPr H B7 Et Me
2,2-Cl2-cPr H B7 CF Me
cPr H B7 Et Me
cPr H B7 CF3 Me
1-Me-cPr H B7 Et Me
1-Me-cPr H B7 CF3 Me
cHex H B7 Et Me
cHex H B7 CF Me
CH2Ph H B7 CF Me
naphthyl-1 H B7 Et Me
naphthyl-1 H B7 CF3 Me
naphthyl-2 H B7 CF3 Me
CO2Me H B7 CF3 Me
CO2Et H B7 CF3 Me
2-thienyl H B7 CF3 Me
TABLE 8
Figure USRE038188-20030715-C00253
Figure USRE038188-20030715-C00254
Figure USRE038188-20030715-C00255
Figure USRE038188-20030715-C00256
Figure USRE038188-20030715-C00257
Figure USRE038188-20030715-C00258
Figure USRE038188-20030715-C00259
Figure USRE038188-20030715-C00260
Figure USRE038188-20030715-C00261
Figure USRE038188-20030715-C00262
Figure USRE038188-20030715-C00263
Figure USRE038188-20030715-C00264
Figure USRE038188-20030715-C00265
Figure USRE038188-20030715-C00266
Figure USRE038188-20030715-C00267
Figure USRE038188-20030715-C00268
Figure USRE038188-20030715-C00269
Figure USRE038188-20030715-C00270
Figure USRE038188-20030715-C00271
Figure USRE038188-20030715-C00272
Figure USRE038188-20030715-C00273
Figure USRE038188-20030715-C00274
Figure USRE038188-20030715-C00275
Figure USRE038188-20030715-C00276
Figure USRE038188-20030715-C00277
Figure USRE038188-20030715-C00278
Figure USRE038188-20030715-C00279
Figure USRE038188-20030715-C00280
Figure USRE038188-20030715-C00281
R1 R2 B W
2-F—Ph H H 2-F
2,6-F2—Ph H (CO(2,4-Me2—Ph) 2-F
tBu H H 2-F
tBu H B7 2-F
tBuCH2 H B6 2-F
EtMe2C H B30 2-F
cHex H B31 2-Cl
1-Me-cHex H B32 2-Br
Ph H B33 2-F
2-F—Ph H B34 2-F
2-Cl H H 2-Me
2-Cl—Ph H CO2iPr 2-nBu
2,6-F2—Ph H CO(2-MeO—Ph) 2-OMe
2,6-Cl2—Ph H H 2-nBeO
1-naphthyl Cl CO(4-MeO—Ph) 2-CF3
2-naphthyl Me CO(2-Me—Ph) 2-OCHF2
tBu H Na 2-CF3
tBu H Ca 2-OCH2CH2CHFCHF2
2-pyridyl H H 2-OCF2CHF2
3-pyridyl H H 2-SMe
4-pyridyl H B7 2-SOMe
Me2C═N— H B10 2-SO2Me
iPr H B13 2-SCBrF2
tBu H B19 2-SCF3
tBuCH2 H B22 2-SOCBrF2
EtMe2C H B23 2-SO2CH2F
cHex H B7 2-SCF3
Ph H B25 2-SCBrF2
2-F—Ph H B26 2-SO2CHF2
2-F—Ph H B27 2-SCBrF2
2-CF3—Ph H B28 2-CH═CCl2
2,6-F2—Ph H CO(2,6-Me2—Ph) 2-OCH2CH═CH2
1-naphthyl H CO(2,6-(MeO)2—Ph) 2-OCH2CH═CCl2
PhCH2 H CO(2-Me-6-NO2—Ph) 2-OCH2CH═CHCl
2-thienyl H CO(3,4,5-(MeO)3—Ph) 2-SCH2CH═CHMe
4-Cl-2-thienyl H SO2(4-Me—Ph) 2-SOCH2CH═CH2
3-MeO-2-pyridyl H CO(2,6-Cl2—Ph) 2-SO2CHMeCH═CH2
2-Cl-3-pyridyl H CO(2,5-Me2—Ph) 2-SCH2CMe═CF2
2,6-Cl2-4-pyridyl H CO(2,6-F2—Ph) 2-SOCH2CF═CF2
EtMeC═N— H B1 2-SO2CH2CH═CF2
Et H B2 2-CCH
tBu H B4 2-CCl
tBuCH2 H H 2-OCH2CCH
EtMe2C H H 2-OCH2CCCl
cHex H H 2-SCH2CCMe
Ph H H 2-SOCH2CCH
2-MeO—Ph H B5 2-SO2CH2CCMe
2-F—Ph H B6 2-SCH2CCBr
2,6-F2—Ph H B7 2-SOCHMeCCCl
2,6-Me2—Ph H B8 2-SO2CH2CCl
1-naphthyl H Ba 2-NO2
PhCH2 H K 2-CN
2-naphthyl H H 2-CO2Me
5-Br-3-thienyl H B3 2-COMe
3-MeO-2-pyridyl H B14 2-O(CO)Me
2-Cl-3-pyridyl H B15 2-NHMe
2,6-Cl2-4-pyridyl H B16 2-NMe
(CH2)4C═N— H B17 3-F
tBu H H 3-Cl
tBuCH2 H H 3-nBu
EtMe2C H H 3-OEt
2-Me-cHex H H 3-CH2CH2CH2CHF2
Ph H B22 3-OCH2CH2CHFCHF2
Ph H B27 3-S-nBu
2-CF3—Ph H B28 3-SOnPr
2,6-F2—Ph H B30 3-SO2iPr
2,6-Me2—Ph H B31 3-SCF3
1-naphthyl H CO(3,4-(MeO)2—Ph) 3-SCH2CH2CHFCHF2
PhCH2 H CO(2,4-Cl2—Ph) 3-SO2CF2CHF2
2-thienyl H CO(3-CF3—Ph) 3-SCH2CMe═CH2
3-Me-2-pyridyl H CO(2-Me2N—Ph) 3-SOCH2CH═CH2
3-NO2-2-pyridyl H COiPr 3-SO2CHMeCH═CH2
3,6-Cl2-2-pyridyl H CO2iPr 3-SCH2CMe═CF2
2-MeS-3-pyridyl H CO2tBu 3-SOCH2CF═CCl2
(CH2)5C═N— H CONHMe 3-SO2CH2CH═CH2Cl
sBu H CONHEt 3-OCH2CCH
tBuCH2 H B19 3-SCH2CCMe
EtMe2C H B18 3-SOCH2CCH
2-Me-cHex H SO2(2-Me—Ph) 3-SO2CH2CCMe
Ph H H 3-NO2
2-CF3O—Ph H H 3-CN
2-MeS—Ph H H 3-CO2Et
2,6-F2—Ph H Na 3-COnPr
2,6-Cl2—Ph H K 3-O(CO)nPr
1-naphthyl H Mg 3-NHBu
3-F-2-pyridyl H Ca 3-NEt2
6-Me-pyridyl H Ba 4-F
4-CF3-3-pyridyl H COCEtMe2 4-Cl
3-NO2-3-pyridyl H CO(3-MeO—Ph) 4-Br
2,4-Me2-3-pyridyl H CO-2-naphtyl 4-I
iBuMeC═N— H CO(4-EtO-3-MeO—Ph) 4-Me
tBu H CO(3-Cl-4-MeO—Ph) 4-tBu
tBu H CO(3-F-4-nBuO—Ph) 4-OMe
tBu H CH2CO2Me 4-CF3
Ph H CH(Me)CO2Et 4-OCHF2
Ph H CMe2CO2nPr 4-SMe
2-pyridyl H CH2CN 4-SOMe
sBu H CH2CH2CH2CN 4-SO2nBu
tBuCH2 H CH2CO2iPr 4-SCF3
EtMe2C H H 4-SOCBrF2
2-Me-cHex H H 4-SO2CH2F
Ph H H 4-OCH2CH═CH2
2-CF3—Ph H H 4-OCH2CH═CCl2
2-NO2—Ph H B3 4-OCH2CCH
2,6-F2—Ph H B4 4-OCH2CCCl
2-Cl-6-F—Ph H B5 4-SCH2CCMe
1-naphthyl H B6 4-SO2CH2CCMe
2-pyridyl H B7 4-NO2
3-pyridyl H B8 4-CN
PhCH2 H B12 4-CO2nBu
2-thienyl H B21 4-COiBu
3-thienyl H B28 4-O(CO)nPr
iBuMeC═N— H CO(2-MeO—Ph) 4-NHnBu
tBu H H 2,3-Cl2
tBu H H 2,4-Cl2
tBu H H 3,4-Cl2
Ph H H 3,5-Cl2
Ph H H 2,5-Cl2
2-pyridyl H B7 2,6-Cl2
sBu H B8 2,6-Cl2
tBuCH2 H B12 2,6-Cl2
EtMe2C H B23 2,3-F2
2-Me-cHex H B26 2,3-F2
Ph H B28 2,3-F2
2-Me—Ph H CONHiPr 2,4-F2
2-MeO—Ph H Ca 2,4-F2
2,6-F2—Ph H Ba 2,5-F2
2,6-Cl2—Ph H H 2,6-F2
1-naphthyl H H 2,6-F2
2-pyridyl H H 2,6-F2
PhCH2 H CO(2,3-Me2—Ph) 2,6-F2
3-pyridyl H CO(3,4-Me2—Ph) 2,6-F2
4-pyridyl H CH2CO2Et 2,6-F2
2-thienyl H CHMeCO2Me 2,6-F2
iBuMeC═N— H CH2CN 2,6-F2
tBu H H 2,6-F2
tBu H B7 2,6-F2
tBu H B8 2,6-F2
tBu H B28 2,6-F2
tBu Me B31 2,6-F2
tBu H B34 2,6-F2
tBu H CO(2-MeO—Ph) 2,6-F2
tBu H CO(2-Cl—Ph) 2,6-F2
tBu H CO(2,6-Me2—Ph) 2,6-F2
tBuCH2 H CO(2,6-(MeO)2—Ph) 2,6-F2
EtMe2C H CO(3,4,5-(MeO)3—Ph) 2,6-F2
cHex H B28 2,6-F2
cHex H B31 2,6-F2
cHex H B34 2,6-F2
1-Me-cHex H SO2(4-Cl—Ph) 2,6-F2
Ph H H 2,6-F2
Ph H B5 2,6-F2
Ph H B6 2,6-F2
2-F—Ph H B14 2,6-F2
3-F—Ph H B19 2,6-F2
4-F—Ph H B23 2,6-F2
2-Cl—Ph H B24 2,6-F2
2,6-F2—Ph H H 2,6-F2
2,6-F2—Ph H Ca 2,6-F2
2,6-F2—Ph Me B7 2,6-F2
2,6-F2—Ph H B9 2,6-F2
1-naphthyl H B10 2,6-F2
2-naphthyl H B16 2,6-F2
2-thienyl H B22 2,6-F2
3-thienyl H B24 2,6-F2
2-pyridyl Cl H 3,4-F2
3-pyridyl H B7 3,5-F2
4-pyridyl H B18 2,5-(CF3)2
nPr2C═N— H B31 2,6-(CF3)2
tBu Et H 3,5-(CF3)2
tBu Br H 5-Br-2-Cl
tBu H SO2(4-Me—Ph) 3-Br-4Me
tBu H COnHex 2-Cl-4-F
tBu H CO(2-Cl-6-F—Ph) 2-Cl-6-F
tBuCH2 H CO(3,5-Cl2-4MeO—Ph) 2-Cl-6-F
EtMe2C H CO(3-Br-4-Me—Ph) 2-Cl-6-F
cHex H H 2-Cl-6-F
cHex H B6 2-Cl-6-F
Ph H B7 2-Cl-6-F
Ph H B8 2-Cl-6-F
2-F—Ph H B34 2-Cl-6-F
3-F—Ph H CO2tBu 2-Cl-6-F
2-Cl—Ph H CHMeCO2Me 2-Cl-6-F
2,6-F2—Ph H B31 3-Cl-4-F
2,6-F2—Ph H K 4-Cl-3-F
tBu H Ba 2-F-6-I
2,6-F2—Ph H CO(4-nBuO—Ph) 2-F-6-I
2,6-F2—Ph H CO(4-Et2N—Ph) 2-F-6-I
2,6-F2—Ph Br CO(3-Me2N—Ph) 2-Cl-5-SMe
1-naphthyl H CO(4-Et—Ph) 2-Cl-5-SCBrF2
2-naphthyl H CO(3-F-4-Me—Ph) 2-Cl-5-SCF3
2-thienyl H CO(3-MeO-4-Me—Ph) 2-Cl-5-SOMe
3-thienyl H CO(2,3,6-F3—Ph) 2-Cl-5-SO2Me
2-pyridyl H CO(2-MeO-5-NO2—Ph) 2-Cl-4-NO2
3-pyridyl H CO(3,5-Me2—Ph) 2,4-(OMe)2
4-pyridyl H H 2,6-(OMe)2
nPr2C═N— H H 2,6-(OMe)2
tBu H H 2,3-Me2
tBu H B1 2,4-Me2
tBu H B2 2,5-Me2
tBuCH2 H B3 2,6-Me2
EtMe2C H B4 2,6-Me2
cHex H B5 2,6-Me2
cHex H B6 3,4-Me2
1-Me-cHex H B7 3,5-Me2
Ph H B8 2-F-4-Me
Ph H B9 2-F-4-Me
Ph H B10 2-F-4-Me
2-F—Ph H B11 3-F-4-Me
2-F—Ph H B12 3-I-4-Me
3-F—Ph H B13 2-OMe-4-SMe
4-F—Ph H B14 3-OMe-4-NO2
2-Cl—Ph H CH2CN 2-Me-4-NO2
2,6-F2—Ph H CMe2CO2Et 2-Me-6-NO2
2,6-F2—Ph H CONHMe 2,3,6-F3
tBu H SO2(4-Cl—Ph) 2,3,6-F3
cHex H CO(2-MeO—Ph) 2,3,6-F3
1-naphthyl H CO(2-Me—Ph) 2,3,6-F3
2-F—Ph H CO(2-Cl—Ph) 2,3,6-F3
2-pyridyl H CO(2,6-(MeO)2—Ph) 2,4,5-F3
3-pyridyl H CO(3,4-Me2—Ph) 2,4,5-F3
4-pyridyl H CO(3-MeO-4-EtO—Ph) 2,4,5-F3
nPr2C═N— H B15 2,3,5-I3
tBu H B16 2,3,5-I3
tBu H B17 2,3,4-(OMe)3
tBu H B18 2,4,5-(OMe)3
tBu H B19 3,4,5-(OMe)3
tBu H B20 2,4,6-Me3
tBuCH2 H B21 2,3,4,5-F4
EtMe2C H B24 2,3,4,5-F4
cHex H B25 2,3,4,5-F4
cHex H B27 2,3,5,6-F4
cHex H B28 2,3,5,6-F4
1-Me-cHex H B29 2,3,5,6-F4
Ph H B30 2,3,5,6-F4
Ph H B31 2,3,4,5,6-F5
Ph H B32 2,3,4,5,6-F5
2-F—Ph H B33 2,3,4,5,6-F5
3-F—Ph H B34 2,3,5,6-F4-4-Me
4-F—Ph H H 2,3,5,6-F4-4-Me
2-Cl—Ph H H 2,3,5,6-F4-4-Me
2,6-F2—Ph H B27 2,3,5,6-F4-4-Me
2,6-F2—Ph H Ca 2,3,5,6-F4-4-Me
TABLE 9
Figure USRE038188-20030715-C00282
Figure USRE038188-20030715-C00283
Figure USRE038188-20030715-C00284
Figure USRE038188-20030715-C00285
Figure USRE038188-20030715-C00286
Figure USRE038188-20030715-C00287
Figure USRE038188-20030715-C00288
Figure USRE038188-20030715-C00289
Figure USRE038188-20030715-C00290
Figure USRE038188-20030715-C00291
Figure USRE038188-20030715-C00292
Figure USRE038188-20030715-C00293
Figure USRE038188-20030715-C00294
Figure USRE038188-20030715-C00295
Figure USRE038188-20030715-C00296
Figure USRE038188-20030715-C00297
Figure USRE038188-20030715-C00298
Figure USRE038188-20030715-C00299
Figure USRE038188-20030715-C00300
Figure USRE038188-20030715-C00301
Figure USRE038188-20030715-C00302
Figure USRE038188-20030715-C00303
Figure USRE038188-20030715-C00304
Figure USRE038188-20030715-C00305
Figure USRE038188-20030715-C00306
Figure USRE038188-20030715-C00307
Figure USRE038188-20030715-C00308
Figure USRE038188-20030715-C00309
Figure USRE038188-20030715-C00310
Figure USRE038188-20030715-C00311
R1 B Y1
Me H H
Et B1 Me
iPr B2 Et
nBu B3 nPr
sBu B4 iBu
tBu H nHex
tBu B7 Me
tBu B8 MeO
tBu B8 MeS
tBu B7 CF3
tBu B5 CF3
tBu B7 CClF2
tBu B8 CF3CF2
tBu 4-Cl—PhCO2 CF3CF2CF2
tPen B6 MeO
nHex B7 EtO
nHep B8 iPrO
nOct B9 sBuO
nNon B10 MeS
nDec B11 EtS
PhCH2 B12 nPrS
Ph(Me)CH B13 tBuS
PhMe2C B14 Ph
PhMe2C B7 Me
PhMe2C B8 Me
PhMe2C B33 Me
PhMe2C B34 Me
PhMe2C B41 Me
PhMe2C B7 CF3
PhMe2C B8 CF3
PhMe2C B34 CF3
4-Cl—PhMe2C B15 Me2N
3-Br—PhEtMeC B16 Et2N
4-Me—Ph(CH2)3 B17 H
CH2═CMe B18 Me
CF3CF2CF2 B19 Et
cPr B20 nPr
cPen B21 iBu
cPen B22 nHex
cPen B23 CF3
cHex B24 CClF2
cHex B7 CF3
cHex B8 CF3
cHex B33 CF3
cHex B34 CF3
cHex B7 Me
cHex B8 Me
cHex B34 Me
1-Me-cHex B7 Me
1-Me-cHex B8 CF3
1-Me-cHex B7 CF3
1-Me-cHex iBuOC(O) CF3
1-Me-cHex B28 EtO
1-Me-cHex B29 iPrO
EtO B30 sBuO
iPrO B31 MeS
CF3O B32 EtS
tBuOC(O) B33 nPrS
Ph B34 tBuS
2-F—Ph B35 Ph
2-F—Ph B36 Me2N
2-Cl—Ph B37 Et2N
2-Cl—Ph B38 Cl
2-Br—Ph B39 Br
2-I—Ph B40 I
2-CF3—Ph B41 H
2-MeO—Ph B42 CF3
3,4-Cl2—Ph CClF2C(O) MeO
2,4-Me2—Ph PhSC(O) MeS
2,6-F2—Ph B7 Me
2,6-F2—Ph B7 CF3
2,6-F2—Ph B8 Me
2,6-F2—Ph B8 CF3
2,6-F2—Ph EtSC(O) H
2,6-F2—Ph tBuC(S) Me
2,6-F2—Ph cPenOC(O) Et
2-pyridyl cHexOC(O) nPr
2-pyridyl B7 Me
2-pyridyl B8 Me
2-pyridyl B7 CF3
2-pyridyl B8 CF3
2-pyridyl iBuOC(O) CF3
2-pyridyl B33 CF3
2-pyridyl B34 CF3
2-pyridyl B34 Me
2-pyridyl 2-pyridyl-C(O) CClF2
2-pyridyl 2-pyridyl-C(O) CF3CF2
2-thienyl 3-pyridyl-C(O) CF3CF2CF2
1-naphthyl 4-pyridyl-C(O) MeO
2-naphthyl H EtO
tBu CClF2C(O) H
tBu PhSC(O) Me
tBu EtSC(O) Et
tBu tBuC(S) nPr
cPr cPenOC(O) iBu
cPen cHexOC(O) nHex
cHex B7 CF3
1-Et-cPr B8 CClF2
1-Me-cPen iBuOC(O) CF3CF2
1-Me-cPen 2-pyridyl-C(O) CF3CF2CF2
2,6-F2—Ph 2-pyridyl-C(O) MeO
2,6-F2—Ph 2-pyridyl-C(O) MeO
2,6-F2—Ph 4-pyridyl-C(O) Me
2,6-F2—Ph 2-pyridyl-C(O) CF3
TABLE 10
Figure USRE038188-20030715-C00312
Figure USRE038188-20030715-C00313
Figure USRE038188-20030715-C00314
Figure USRE038188-20030715-C00315
Figure USRE038188-20030715-C00316
Figure USRE038188-20030715-C00317
Figure USRE038188-20030715-C00318
Figure USRE038188-20030715-C00319
Figure USRE038188-20030715-C00320
Figure USRE038188-20030715-C00321
Figure USRE038188-20030715-C00322
Figure USRE038188-20030715-C00323
Figure USRE038188-20030715-C00324
Figure USRE038188-20030715-C00325
Figure USRE038188-20030715-C00326
Figure USRE038188-20030715-C00327
Figure USRE038188-20030715-C00328
Figure USRE038188-20030715-C00329
R1 B A R1 B A
Et H A1 tBu B15 A8
iPr B7 A2 tBu B34 A8
iBu B7 A1 tBu H A9
sBu B7 A2 tBu B7 A9
tBu B7 A1 tBu B8 A9
tBu B8 A1 tBu B15 A9
tBu B15 A1 tBu B34 A9
tBu B34 A1 tBu CO2-iBu A9
tBu B7 A2 tBu H A10
tBu B8 A2 tBu B7 A10
tBu B15 A2 tBu B8 A10
tBu B34 A2 tBu B15 A10
tBu CO2-iBu A2 tBu B34 A10
tBu B7 A3 tBu CO2-iBu A10
tBu B7 A4 tBu R A11
tBu B7 A5 tBu B7 A11
tBu B7 A6 tBu B8 A11
tBu H A7 tBu B15 A11
tBu B7 A7 tBu H A12
tBu B8 A7 tBu B7 A12
tBu B15 A7 tBu B8 A12
tBu B34 A7 tBu B15 A12
tBu H A8 tBu B34 A12
tBu B7 A8 tBu CO2-iBu A12
tBu B8 A8 tBu H A13
tBu B7 A13 tBu B17 A27
tBu B8 A13 tBu B18 A28
tBu B15 A13 tBu B19 A29
tBu B34 A13 tBu B7 A30
tBu CO2-iBu A13 tBu B8 A30
tBu H A14 tBu B15 A30
tBu B7 A14 tBu B20 A31
tBu B16 A14 tBu H A32
tBu B27 A14 tBu B7 A32
tBu B7 A15 tBu B8 A32
tBu B8 A16 tBu B15 A32
tBu B9 A17 tBu B34 A32
tBu B10 A18 tBu CO2-iBu A32
tBu B11 A19 tBu B21 A33
tBu B12 A20 tBu B22 A34
tBu B13 A21 tBu B23 A35
tBu B7 A22 tBu B24 A36
tBu B8 A22 tBuCH2 B3 A1
tBu B7 A23 tBuCH2 B7 A2
tBu B8 A23 tBuCH2 B8 A2
tBu B15 A23 Et(Me)2C B15 A2
tBu B34 A23 Et(Me)2C B16 A2
tBu B14 A24 Et(Me)2C B34 A2
tBu B15 A25 Et(Me)2C H A2
tBu B16 A26 Et(Me)2C B7 A2
nHex B7 A1 Ph B7 A10
nHep B7 A2 Ph B7 A13
nOct B7 A1 Ph B7 A32
nNon B7 A2 2-F—Ph B7 A1
nDec B7 A7 2-F—Ph B7 A1
cPr B7 A8 2-F—Ph B7 A7
1-Me-cPr B7 A1 2-F—Ph B7 A8
1-Me-cPr B7 A2 2-F—Ph B7 A9
1-Me-cPr B8 A2 2-F—Ph B7 A10
1-Me-cPr B34 A2 2-F—Ph B7 A13
1-Me-cPr H A2 2-F—Ph B8 A32
cPen B7 A2 2-Cl—Ph B7 A1
cHex B7 A1 2-Cl—Ph B7 A2
cHex B7 A2 2-Cl—Ph B7 A7
cHex B8 A2 2-Cl—Ph B7 A8
cHex B15 A2 2-Cl—Ph B7 A9
cHex B34 A2 2-Cl—Ph B7 A10
cHex B35 A2 2-Cl—Ph B7 A13
cHex B36 A1 2-Cl—Ph B8 A30
cHex B37 A2 2-Cl—Ph B34 A32
Ph H A2 2-Br—Ph B7 A1
Ph B7 A2 2-I—Ph B7 A2
Ph B7 A7 2-Me—Ph B7 A7
Ph B7 A8 2-Me—Ph B7 A8
Ph B7 A9 2-Me—Ph B7 A9
2-Me—Ph B7 A1 2,6-Cl2—Ph B7 A1
2-Me—Ph B7 A2 2,6-Cl2—Ph B7 A2
2-MeO—Ph B2 A7 2,6-Cl2—Ph B7 A7
2-CF3—Ph B3 A8 2,6-F2—Ph B7 A1
2-NO2—Ph B4 A9 2,6-F2—Ph B7 A2
2-CN—Ph B5 A10 2,6-F2—Ph B7 A7
2-CBrF2O—Ph B6 A11 2,6-F2—Ph B7 A8
2-CF3O—Ph B7 A12 2,6-F2—Ph B7 A9
2-MeS—Ph B8 A13 2,6-F2—Ph B7 A10
2-nBuS—Ph B9 A14 2,6-F2—Ph B7 A13
2-MeSO—Ph B10 A15 2,6-F2—Ph B7 A21
2-MeSO2—Ph B11 A16 2,6-F2—Ph B7 A32
2-CH2═CHCH2S—Ph B12 A17 2,6-F2—Ph B3 A2
2-CH2═CHCH2SO—Ph B13 A18 2,6-F2—Ph B4 A2
2-CH2═CHCH2SO2—Ph B14 A19 2,6-F2—Ph B5 A2
2-CF3S—Ph B15 A20 2,6-F2—Ph B8 A2
2-CHF2S—Ph B16 A21 2,6-F2—Ph B15 A2
2-CBrF2SO—Ph B17 A22 2,6-F2—Ph B19 A2
2-CF3SO2—Ph B18 A23 2,6-F2—Ph B32 A2
2-CHO—Ph B19 A24 2,6-F2—Ph B33 A2
2-OH—Ph B20 A25 2,6-F2—Ph B34 A2
2-Me2N—Ph B21 A26 2,6-F2—Ph B35 A2
3-Ph—Ph B22 A27 2,6-F2—Ph B37 A2
4-PhO—Ph B23 A28 2,6-F2—Ph B40 A2
2-MeOC(O)—Ph B24 A29 2,6-F2—Ph B43 A2
Cl B7 A1 ClCC B3 A23
PhCH2 B7 A1 2,2-Cl2-cPr B4 A23
PhCH2 B7 A2 2,2-F2-cBu B5 A23
PhCH2 B8 A2 MeO B6 A24
PhCH2 B34 A2 nHexO B7 A25
(4-Cl—Ph)CH2 B7 A30 CH2═CHCH2O B8 A26
(4-Me—Ph)CH2 B7 A31 CHCCH2O B9 A27
(3,4-Cl2—Ph)CH2 B7 A32 CF3O B10 A28
(2,4-Me2—Ph)CH2 B7 A33 ClCH═CHCH2O B11 A29
PhMeCH B7 A34 MeS B12 A30
Ph(Me)2C B3 A1 MeSO B13 A30
Ph(Me)2C B7 A1 MeSO2 B14 A30
Ph(Me)2C B3 A2 Me2C═CHCH2S B15 A31
Ph(Me)2C B7 A2 Me2C═CHCH2SO B16 A32
Ph(Me)2C B8 A2 Me2C═CHCH2SO2 B17 A32
Ph(Me)2C B33 A2 CHCCH2S B18 A32
Ph(Me)2C B34 A2 CHCCH2SO B19 A1
Ph(Me)2C B35 A2 CHCCH2SO2 B20 A2
Ph(Me)2C B7 A13 CF3S B21 A2
Ph(Me)2C B8 A13 CF3SO B22 A13
Ph(Me)2C B34 A13 CF3SO2 B23 A13
CF3 B15 A35 ClCH═CHCH2S B24 A1
CF3CH2 B6 A36 ClCH═CHCH2SO B25 A1
CH2═CMe B6 A1 ClCH═CHCH2SO2 B26 A2
Cl2C═CH B29 A2 ClCCCH2S B27 A2
BrCCCH2SO B28 A1 2-pyridyl H A7
ClCCH2SO2 B29 A2 2-pyridyl B7 A7
1-naphthyl B30 A2 2-pyridyl B8 A7
2-napthyl B31 A13 2-pyridyl B15 A7
MeC(O) B32 A13 2-pyridyl B34 A7
MeC(O)O B33 A1 2-pyridyl H A8
CF3C(O)O B34 A1 2-pyridyl B7 A8
2-thienyl B35 A2 2-pyridyl B8 A8
3-thienyl B36 A2 2-pyridyl B15 A8
Me2C═N B37 A1 2-pyridyl B34 A8
EtMeC═N B38 A1 2-pyridyl H A9
PhCH═N B39 A2 2-pyridyl B7 A9
PhMeC═N B40 A2 2-pyridyl B8 A9
2-pyridyl B7 A1 2-pyridyl B15 A9
2-pyridyl B8 A1 2-pyridyl B34 A9
2-pyridyl B15 A1 2-pyridyl CO2-iBu A9
2-pyridyl B34 A1 2-pyridyl H A10
2-pyridyl B7 A2 2-pyridyl B7 A10
2-pyridyl B8 A2 2-pyridyl B8 A10
2-pyridyl B15 A2 2-pyridyl B15 A10
2-pyridyl B34 A2 2-pyridyl B34 A10
2-pyridyl CO2-iBu A2 2-pyridyl CO2-tBu A10
2-pyridyl B7 A3 2-pyridyl H A11
2-pyridyl B7 A4 2-pyridyl B7 A11
2-pyridyl B7 A5 2-pyridyl B8 A11
2-pyridyl B7 A6 2-pyridyl B15 A11
2-pyridyl H A12 2-pyridyl B8 A23
2-pyridyl B7 A12 2-pyridyl B15 A23
2-pyridyl B8 A12 2-pyridyl B34 A23
2-pyridyl B15 A12 2-pyridyl B14 A24
2-pyridyl B34 A12 2-pyridyl B15 A25
2-pyridyl CO2-tBu A12 2-pyridyl B16 A26
2-pyridyl H A13 2-pyridyl B17 A27
2-pyridyl B7 A13 2-pyridyl B18 A25
2-pyridyl B8 A13 2-pyridyl B19 A29
2-pyridyl B15 A13 2-pyridyl B7 A30
2-pyridyl B34 A13 2-pyridyl B8 A30
2-pyridyl CO2-tBu A13 2-pyridyl B15 A30
2-pyridyl H A14 2-pyridyl B20 A31
2-pyridyl B7 A14 2-pyridyl H A32
2-pyridyl B16 A14 2-pyridyl B7 A32
2-pyridyl B17 A14 2-pyridyl B8 A32
2-pyridyl B7 A15 3-pyridyl B7 A1
2-pyridyl B8 A16 3-pyridyl B34 A2
2-pyridyl B9 A17 3-pyridyl CO2-iBu A2
2-pyridyl B10 A18 3-pyridyl B7 A13
2-pyridyl B11 A19 3-pyridyl B8 A13
2-pyridyl B12 A20 4-pyridyl B7 A1
2-pyridyl B13 A21 4-pyridyl B8 A1
2-pyridyl B7 A22 4-pyridyl B15 A2
2-pyridyl B8 A22 4-pyridyl B34 A2
TABLE 11
Figure USRE038188-20030715-C00330
Figure USRE038188-20030715-C00331
Figure USRE038188-20030715-C00332
Figure USRE038188-20030715-C00333
Figure USRE038188-20030715-C00334
G B Y1 Y2 Y3
2-Cl H Me Me Me
3-Cl B1 Me Cl Me
4-Cl B2 Cl Me Me
4-Br B3 Cl Cl Me
4-I B4 CF3 Cl Me
4-F B5 CF3 H Me
4-Me B6 H CF3 Me
4-Et B7 H Cl Me
4-iPr B8 Cl H Me
4-nBu B9 H H Me
4-iBu B10 OMe Cl Me
4-sBu B11 SMe Cl Me
4-sBu H Me Me Me
4-sBu B16 Me Me Me
4-sBu B17 Me Me Me
4-sBu B7 Me Cl Me
4-sBu B8 Me Cl Me
4-sBu B16 Me Cl Me
4-sBu B17 Me Cl Me
4-sBu B34 Me Cl Me
4-sBu B3 CF3 Cl Me
4-sBu B7 CF3 Cl Me
4-sBu B8 CF3 Cl Me
4-sBu B34 CF3 Cl Me
4-sBu B7 Cl Cl Me
4-sBu B17 Cl Cl Me
4-tBu B12 SCF3 Cl Me
4-tBu H Me Me Me
4-tBu B3 Me Cl Me
4-tBu B7 Cl Me Me
4-tBu B8 Cl Cl Me
4-tBu B15 Cl Cl Me
4-tBu B16 Cl Cl Me
4-tBu B28 Cl Cl Me
4-tBu B30 Cl Cl Me
4-tBu B34 Cl Cl Me
4-tBu CO-nC8H17 Cl Cl Me
4-tBu CO-nC15H31 Cl Cl Me
4-tBu CO2-nHex Cl Cl Me
4-tBu CO2-nC10H21 Cl Cl Me
4-tBu H CN Cl Me
4-tBu H CF3 Cl Me
4-tBu B3 CF3 Cl Me
4-tBu B7 CF3 Cl Me
4-tBu B8 CF3 Cl Me
4-tBu B15 CF3 Cl Me
4-tBu B16 CF3 Cl Me
4-tBu B28 CF3 Cl Me
4-tBu B30 CF3 Cl Me
4-tBu B16 Cl Cl Me
4-tBu B16 CF3 Cl Me
4-tBu B17 CF3 Cl Me
4-tBu B17 Cl Cl Me
4-tBu CO2-nC10H21 CF3 Cl Me
4-tBu CH2OEt CF3 Cl Me
4-tBu B7 Me Cl Me
4-tBu B7 Me Me Me
4-tBu B7 CN Cl Me
4-tBu B16 CN Cl Me
4-tBu B3 CN Cl Me
4-tBu 2-(4-tBu—Ph)- CF3 Cl Me
3,3-Me2-cPrC(O)
4-tBu B45 CF3 Cl Me
4-tBuCH2 B3 CF3 Cl Me
4-tBuCH2 B7 Me Me Me
4-tBuCH2 B16 Me Cl Me
4-tBuCH2 B7 CF3 Cl Me
4-tBuCH2 B8 CF3 Cl Me
4-tBuCH2 B7 Cl Cl Me
4-Et(Me)2C H CF3 Cl Me
4-Et(Me)2C B3 CF3 Cl Me
4-Et(Me)2C B7 CF3 Cl Me
4-Et(Me)2C B8 CF3 Cl Me
4-Et(Me)2C B34 CF3 Cl Me
4-Et(Me)2C B42 CF3 Cl Me
4-Et(Me)2C B16 Me Me Me
4-Et(Me)2C B17 Me Me Me
4-Et(Me)2C H Cl Me Me
4-Et(Me)2C B7 Cl Cl Me
4-Et(Me)2C B8 Cl Cl Me
4-Et(Me)2C B7 CF3 Me Me
4-Et(Me)2C B7 CN Cl Me
4-Et(Me)2C B4 H Cl Me
4-Et(Me)2C B5 Cl H Me
4-Et(Me)2C B6 H H Me
4-Et(Me)2C B3 Cl Cl Me
4-Et(Me)2C B16 Cl Cl Me
4-Et(Me)2C B17 Cl Cl Me
4-Et(Me)2C B24 Cl Cl Me
4-nHex B34 CF3 Cl Me
4-nHep B42 CF3 Cl Me
4-nOct B43 Me Me Me
4-nNon B43 Me Cl Me
4-nDec H Cl Me Me
4-(Me)2(CN)C B7 Cl Cl Me
4-PhCH2 B7 CF3 Cl Me
4-Ph(Me)2C B7 CF3 Me Me
4-(4-F—Ph)(Me)2C B7 CN Cl Me
4-MeCH═CH B4 H Cl Me
4-MeCC B5 Cl H Me
3-CF3 B6 H H Me
4-CF3 B7 OMe Cl Me
4-CF3 B8 SMe Cl Me
4-CF3 B9 SCF3 Cl Me
4-CF3 B16 Me Me Me
4-CF3 B17 Me Me Me
4-CF3 B16 Me Cl Me
4-CF3 B17 Cl Me Me
4-CF3 B7 Cl Cl Me
4-CF3 B7 CF3 Cl Me
4-CF3 B7 CN Cl Me
4-CF3 B3 Cl Cl Me
4-CF3CH2 B7 Me Cl Me
4-Cl2C═CHCH2 B8 Cl Me Me
4-BrCC B7 Cl Cl Me
4-(2,2-F2)cBuCH2 B7 CF3 Cl Me
4-(1-Me)cPr B16 CN Cl Me
4-cHex B7 Cl Cl Me
4-(1-Me)cHex B8 CF3 Cl Me
4-MeO B7 Cl H Me
4-iPrO B7 Cl Cl Me
4-iPrO B7 CF3 Cl Me
4-iPrO B15 CF3 Cl Me
4-iPrO B7 Me Me Me
4-iPrO B16 Me Me Me
4-iPrO B17 Me Me Me
4-iPrO B23 SCF3 Cl Me
4-tBuO B7 Cl Cl Me
4-tBuO B8 Cl Cl Me
4-tBuO B7 CF3 Cl Me
4-nHexO B8 CF3 Cl Me
4-nOctO B34 CF3 Cl Me
4-nDecO H CF3 Cl Me
4-CH2═CHCH2O B7 CF3 Cl Me
4-CHCCH2O B8 CF3 Cl3 Me
4-CHF2O B34 CF3 Cl Me
4-CHF2O B7 Me Me Me
4-CHF2O B35 Me Cl Me
4-CHF2O B36 Cl Cl Me
4-CHF2O B7 Cl Cl Me
4-CBrF2O B8 Cl Cl Me
4-CBrF2O B34 Cl Cl Me
4-CBrF2O B40 Me Me Me
4-CBrF2O B41 Me Cl Me
4-CBrF2O B42 Cl Me Me
4-CBrF2O B43 Cl Cl Me
4-CBrF2O B44 CF3 Cl Me
4-CBrF2O COCO2Me CF3 H Me
4-CBrF2O H H CF3 Me
4-CBrF2O B1 H Cl Me
4-CF3O B2 Cl H Me
4-CF3O B3 H H Me
4-CF3O B4 OMe Cl Me
4-CF3O B5 SMe Cl Me
4-CF3O B6 SCF3 Cl Me
4-CF3O B7 Me Me Me
4-CF3CH2O B8 Me Me Me
4-CF2═CHCH2CH2O B9 Me Cl Me
4-CCl2═CHCH2O B10 Cl Me Me
4-ClCCCH2O B11 Cl Cl Me
4-MeS B12 CF3 Cl Me
4-sBuS H CF3 H Me
4-EtSO B3 H CF3 Me
4-MeSO2 H CF3 Cl Me
4-MeSO2 B3 CF3 Cl Me
4-MeSO2 B32 CF3 Cl Me
4-MeSO2 B33 CF3 Cl Me
4-EtSO2 H CF3 Cl Me
4-EtSO2 B3 Cl Cl Me
4-iPrSO2 B32 Cl Cl Me
4-iPrSO2 B33 Cl Cl Me
4-tBuSO2 B7 Cl Cl Me
4-tBuSO2 B33 CF3 Cl Me
4-MeCH═CHCH2S B15 H H Me
4-CH2═CHCH2SO B16 OMe Cl Me
4-CH2═CHCH2SO2 B28 SMe Cl Me
4-CHCCH2S B30 SCF3 Cl Me
4-CHCCH2SO B34 Me Me Me
4-CHCCH2SO2 CO-nC8H17 Me Me Me
4-CHF2S H CF3 Cl Me
4-CHF2S B7 CF3 Cl Me
4-CHF2S B8 CF3 Cl Me
4-CHF2S B15 CF3 Cl Me
4-CHF2S B29 CF3 Cl Me
4-CHF2S H Cl Cl Me
4-CHF2S B7 Cl Cl Me
4-CHF2S B15 Cl Cl Me
4-CBrF2S B7 Cl Cl Me
4-CBrF2S B15 Cl Cl Me
4-CBrF2S B30 Cl Cl Me
4-CBrF2S B43 Cl Cl Me
4-CBrF2S CO-nC15H31 Me Cl Me
4-CBrF2S CO2-nHex CF3 Cl Me
4-CBrF2S H CF3 Cl Me
4-CBrF2S B7 CF3 Cl Me
4-CBrF2S B8 CF3 Cl Me
4-CBrF2S B15 CF3 Cl Me
4-CBrF2S B28 CF3 Cl Me
4-CBrF2S B34 CF3 Cl Me
4-CBrF2S B7 Me Cl Me
4-CF3S CO2-nC10H21 Cl Cl Me
4-CF3S H Cl Cl Me
4-CF3S B3 Cl Cl Me
4-CF3S B7 Cl Cl Me
4-CF3S B8 Cl Cl Me
4-CF3S B15 Cl Cl Me
4-CF3S H CF3 Cl Me
4-CF3S B7 CF3 Cl Me
4-CF3S B8 CF3 Cl Me
4-CF3S B15 CF3 Cl Me
4-CF3S B34 CF3 Cl Me
4-CF3S CO2-nC12H25 CF3 Cl Me
4-CF3S CO-nC15H31 CF3 Cl Me
4-CF3S CO-nC16H33 Me Me Me
4-CF3S CO-nC17H35 Me Cl Me
4-CF3CH2S CO-nC18H37 CF3 Cl Me
4-CHF2CF2S CO-nC19H39 CF3 H Me
4-CHF2SO CO-nC20H41 H CF3 Me
4-CBrF2SO H H Cl Me
4-CBrF2SO B3 CF3 Cl Me
4-CBrF2SO B7 CF3 Cl Me
4-CBrF2SO B24 CF3 Cl Me
4-CBrF2SO B32 CF3 Cl Me
4-CBrF2SO B33 CF3 Cl Me
4-CF3SO H Cl Cl Me
4-CF3SO B3 Cl Cl Me
4-CF3SO B7 Cl Cl Me
4-CF3SO B33 Cl H Me
4-CF3CH2SO2 B15 H H Me
4-CHF2CF2SO2 B16 OMe Cl Me
4-CHF2SO2 B28 SMe Cl Me
4-CHF2SO2 B7 CF3 Cl Me
4-CHF2SO2 B24 CF3 Cl Me
4-CHF2SO2 B32 CF3 Cl Me
4-CHF2SO2 B33 CF3 Cl Me
4-CHF2SO2 H Cl Cl Me
4-CHF2SO2 B3 Cl Cl Me
4-CHF2SO2 B7 Cl Cl Me
4-CHF2SO2 B33 Cl H Me
4-CBrF2SO2 H SCF3 Cl Me
4-CBrF2SO2 B2 Cl Cl Me
4-CBrF2SO2 B3 Cl Cl Me
4-CBrF2SO2 B18 Cl Cl Me
4-CBrF2SO2 B19 Cl Cl Me
4-CBrF2SO2 B33 Cl Cl Me
4-CBrF2SO2 H CF3 Cl Me
4-CBrF2SO2 B3 CF3 Cl Me
4-CBrF2SO2 B7 CF3 Cl Me
4-CBrF2SO2 B20 CF3 Cl Me
4-CBrF2SO2 B32 CF3 Cl Me
4-CBrF2SO2 B33 CF3 Cl Me
4-CBrF2SO2 B37 CF3 Cl Me
4-CBrF2SO2 B7 Me Me Me
4-CBrF2SO2 B15 Me Me Me
4-CBrF2SO2 B17 Me Me Me
4-CBrF2SO2 B7 Me Cl Me
4-CBrF2SO2 B16 Me Cl Me
4-CF3SO2 B16 Me Me Me
4-CF3SO2 B7 Cl Cl Me
4-CF3SO2 B15 Cl Cl Me
4-CF3SO2 B3 CF3 Cl Me
4-CF3SO2 B7 CF3 Cl Me
4-CF3SO2 B15 Me Me Me
4-CF3SO2 B7 Me Cl Me
4-CF3SO2 B8 Me Cl Me
4-Cl2C═CHCH2S B16 Me Me Me
4-Cl2C═CHCH2SO B17 Me Cl Me
4-Cl2C═CHCH2SO2 B17 Cl Me Me
4-CBrCCH2S CO2-nC10H21 Cl Cl Me
4-CBrCCH2SO B33 CF3 Cl Me
4-CBrCCH2SO2 B7 CF3 H Me
4-CHO B7 H CF3 Me
4-NO2 B8 H Cl Me
4-CN B16 Cl H Me
4-(Me)2N B3 H H Me
4-Me(MeCO)N B7 OMe Cl Me
4-PhMeN B8 SMe Cl Me
4-PhCH2(MeCO)N B15 SCF3 Cl Me
4-(1-naphthyl) B16 Me Me Me
4-(2-naphthyl) B28 Me Me Me
4-(2-Cl—Ph)CH2O B30 Me Cl Me
4-(3-Cl—Ph)CH2O B34 Cl Me Me
4-(4-Cl—Ph)CH2O B7 CF3 Cl Me
4-(4-Cl—Ph)CH2O B7 Cl Cl Me
4-(4-Cl—Ph)CH2O B37 Cl Cl Me
4-(4-F—Ph)CH2O B42 CF3 Cl Me
4-(2-Me—Ph)CH2O B43 CF3 H Me
4-(4-Me—Ph)CH2O B43 H CF3 Me
4-(4-Et—Ph)CH2O H H Cl Me
3-(2,4-Cl2—Ph)CH2O B7 Cl H Me
4-(3,4-Cl2—Ph)CH2O B7 H H Me
4-(2,5-Me2—Ph)CH2O B7 OMe Cl Me
4-(2,3,4,5,6-F5—Ph)CH2O B7 SMe Cl Me
4-MeOC(O) B4 SCF3 Cl Me
4-EtOC(O) B5 Me Me Me
4-nPrOC(O) B6 Me Me Me
4-iPrOC(O) B7 Me Cl Me
4-iBuOC(O) B8 Cl Me Me
4-tBuOC(O) B9 Cl Cl Me
4-tBuCH2OC(O) B7 Cl Cl Me
4-tBuCH2OC(O) B15 Cl Cl Me
4-tBuCH2OC(O) B34 Cl Cl Me
4-tBuCH2OC(O) B7 CF3 Cl Me
4-tBuCH2OC(O) B15 CF3 Cl Me
4-tBuCH2OC(O) B34 CF3 Cl Me
4-tBuCH2OC(O) B10 CF3 Cl Me
4-Et(Me)2COC(O) B11 CF3 H Me
4-nHexOC(O) B7 H CF3 Me
4-MeOCH2 B8 H Cl Me
4-EtOCH2 B7 Cl H Me
4-iPrOCH2 B7 H H Me
4-MeC(O) B16 OMe Cl Me
4-EtC(O) B7 SMe Cl Me
4-iPrC(O) B8 SCF3 Cl Me
4-tBuC(O) H Cl Cl Me
4-tBuC(O) B3 Cl Cl Me
4-tBuC(O) B7 Cl Cl Me
4-tBuC(O) B3 CF3 Cl Me
4-tBuC(O) B7 CF3 Cl Me
4-tBuC(O) B15 CF3 Cl Me
4-tBuC(O) B7 Me Me Me
4-tBuC(O) B17 Me Me Me
4-tBuC(O) B16 Me Cl Me
4-CF3C(O) B7 Me Me Me
4-CF3CF2C(O) B8 Me Cl Me
4-CF2CF2CF2C(O) B22 Cl Me Me
4-MeC(O)O B23 Cl Cl Me
4-iPrC(O)O B7 CF3 Cl Me
4-tBuC(O)O B8 CF3 H Me
4-CF3C(O)O B7 H CF3 Me
4-CF2CF2CF2C(O)O B8 H Cl Me
4-Me2NC(O)O B34 Cl H Me
4-Et2NC(O)O H H H Me
4-(nPr)2NC(O)O B7 OMe Cl Me
3-Ph B8 SMe Cl Me
4-Ph B34 SCF3 Cl Me
4-(4-F—Ph) B7 Cl Cl Me
4-(4-F—Ph) B7 CF3 Cl Me
3-PhO B7 Cl Cl Me
3-PhO B15 CF3 Cl Me
4-PhO B7 Me Me Me
4-(4-F—Ph)O B35 Me Cl Me
4-(4-Cl—Ph)O B36 Cl Me Me
4-(4-Br—Ph)O B7 Cl Cl Me
4-(4-Me—Ph) B8 CF3 Cl Me
4-(2-Cl—Ph)O B34 CF3 H Me
4-(2-F—Ph)O B40 H CF3 Me
4-(3-Cl—Ph)O B41 H Cl Me
4-(4-Cl—Ph)O B42 Cl H Me
4-(2,4-Cl2—Ph)O B43 H H Me
4-(3,4-Cl2—Ph)O B44 OMe Cl Me
4-(3,4,5-Cl3—Ph)O COCO2Me SMe Cl Me
4-(2-Me—Ph)O H SCF3 Cl Me
4-(4-Me—Ph)O B1 Me Me Me
4-(3-Cl-4-Me—Ph)O B2 H CF3 Me
4-(2-pyridyl) B3 H Cl Me
4-(5-CF3-pyridin-2-yl) B4 Cl H Me
4-(2-pyridyl)O B7 Cl Cl Me
4-(2-pyridyl)O B15 Cl Cl Me
4-(2-pyridyl)O B7 CF3 Cl Me
4-(2-pyridyl)O B8 CF3 Cl Me
4-(2-pyridyl)O B34 CF3 Cl Me
4-(2-pyridyl)O B5 Cl Cl Me
4-(5-CF3-pyridin-2-yl)O B7 Cl Cl Me
4-(5-CF3-pyridin-2-yl)O B8 Cl Cl Me
4-(5-CF3-pyridin-2-yl)O B15 CF3 Cl Me
4-(5-CF3-pyridin-2-yl)O B7 CF3 Cl Me
4-(5-CF3-pyridin-2-yl)O B15 CF3 Cl Me
4-(5-CF3-pyridin-2-yl)O B34 Me Cl Me
4-(3-Cl-5-CF3-pyridin-2-yl) B7 Cl Cl Me
4-(3-Cl-5-CF3-pyridin-2-yl) B15 Cl Cl Me
4-(3-Cl-5-CF3-pyridin-2-yl) B34 Cl Cl Me
4-(3-Cl-5-CF3-pyridin-2-yl) B7 CF3 Cl Me
4-(3-Cl-5-CF3-pyridin-2-yl) B15 CF3 Cl Me
4-(3-Cl-5-CF3-pyridin-2-yl) B17 CF3 Cl Me
4-(3-Cl-5-CF3-pyridin-2-yl) H Cl Cl Me
4-(5-Cl-thiophen-2-yl) B8 Cl Cl Me
3-OCH2O-4 B9 Cl Cl Me
4-OCF2O-4 B10 CF3 Cl Me
4-MeCH═N B11 CF3 Cl Me
4-Me2C═N B12 CF3 Cl Me
4-MeEtC═N H Cl Cl Me
4-PhCH═N B3 Cl Cl Me
4-PhMeC═N B7 Cl Cl Me
4-PhCH2CH═N B8 CF3 Cl Me
4-cC6H10═N B15 CF3 Cl Me
3-CH2CH2CH2-4 B16 CF3 Cl Me
3-CH2CH2CH2CH2-4 B28 Cl Cl Me
4-PhC(O) H Cl Cl Me
4-PhC(O) B7 Cl Cl Me
4-PhC(O) B7 Cl Cl Me
4-PhC(O) B33 CF3 Cl Me
4-(2-Cl—Ph)C(O) B7 CF3 Cl Me
4-(4-F—Ph)C(O) H CF3 Cl Me
4-(4-Cl—Ph)C(O) B7 Cl Cl Me
4-(4-Cl—Ph)C(O) B15 Cl Cl Me
4-(4-Cl—Ph)C(O) B34 Cl Cl Me
4-(4-Me—Ph)C(O) B3 CF3 Cl Me
4-(4-Me—Ph)C(O) B16 CF3 Cl Me
4-(3,4-Cl2—Ph)C(O) B45 CF3 Cl Me
3,4-Cl2 B15 Cl Cl Me
3-Cl-4-F B7 Cl Cl Me
2,6-F2 B15 CF3 Cl Me
3-Cl-4-CF3 B7 CF3 Cl Me
4-tBu-3-Cl B7 Cl Cl Me
4-tBu-3-Cl B15 CF3 Cl Me
4-tBuCH2-3-Cl B7 Cl Cl Me
4-nHep-3-Cl B15 CF3 Cl Me
3-Cl-4-iPrO B7 Cl Cl Me
3-Cl-4-iPrO B7 CF3 Cl Me
3-Cl-4-nHepO B15 CF3 Cl Me
3-Cl-4-(3,4-Cl2—PhCH2)O H CF3 Cl Me
3-Cl-4-PhCH2O B7 CF3 Cl Me
3,4-(MeO)2 B16 CF3 Cl Me
4-MeO-3-Me B17 CF3 Cl Me
4-OH-3,5-(tBu)2 B3 CF3 Cl Me
3,4,5-Cl3 B15 CF3 Cl Me
2,6-Cl2-4-CF3 B7 CF3 Cl Me
2,6-F2-4-CF3 B15 Cl Cl Me
2,6-F2-4-CF3O B7 CF3 Cl Me
3,5-Cl2-4-tBu B7 Cl Cl Me
3,5-Cl2-4-tBuCH2 B15 CF3 Cl Me
3,5-Cl2-4-nDec B7 Cl Cl Me
3,5-Cl2-4-PhCH2O B15 CF3 Cl Me
2,3,5,6-F4-4-Me B3 CF3 Cl Me
2,3,4,5,6-F5 B33 CF3 Cl Me
TABLE 12
Figure USRE038188-20030715-C00335
Figure USRE038188-20030715-C00336
Figure USRE038188-20030715-C00337
Figure USRE038188-20030715-C00338
Figure USRE038188-20030715-C00339
Figure USRE038188-20030715-C00340
Figure USRE038188-20030715-C00341
Figure USRE038188-20030715-C00342
Figure USRE038188-20030715-C00343
Figure USRE038188-20030715-C00344
Figure USRE038188-20030715-C00345
G B Y1 Y2
2-Cl H Me Me
3-Cl B1 H H
4-Cl B2 Me H
4-Br B3 H Me
4-I B4 Me Me
4-F B5 CF3 Me
4-Me B6 Cl Me
4-Et B7 H Me
4-iPr B8 Cl Me
4-nBu B9 H Me
4-iBu B10 OMe Me
4-sBu B11 SMe Me
4-sBu H Me Me
4-sBu B16 Et Me
4-sBu B17 Cl Me
4-sBu B7 Cl Cl
4-sBu B8 CF3 Me
4-sBu B16 Me CF3
4-sBu B17 Me Me
4-sBu B34 CF3 Me
4-sBu B3 CF3 Me
4-sBu B7 CF3 Me
4-sBu B8 Cl Me
4-sBu B34 Me Cl
4-sBu B7 H H
4-sBu B17 CF3 Me
4-tBu B12 SCF3 Me
4-tBu H Me Me
4-tBu B3 Me Me
4-tBu B7 Me Me
4-tBu B8 Et Me
4-tBu B15 Me nPr
4-tBu B16 OMe OMe
4-tBu B28 Cl Cl
4-tBu B30 OCHF2 Me
4-tBu B34 CF3 CF3
4-tBu CO-nC8H17 H H
4-tBu CO-nC15H31 Cl Cl
4-tBu CO2-nHex Me Me
4-tBu CO2-nC10H21 Me Me
4-tBu H CN Me
4-tBu H CF3 Me
4-tBu B3 CF3 Me
4-tBu B7 CF3 Me
4-tBu B8 CF3 Me
4-tBu B15 CF3 Me
4-tBu B16 CF3 Me
4-tBu B28 CF3 Me
4-tBu B30 CF3 Me
4-tBu B16 Cl Cl
4-tBu B16 CF3 Me
4-tBu B17 CF3 Me
4-tBu B17 Me Me
4-tBu CO2-nC10H21 CF3 Me
4-tBu CH2OEt CF3 Me
4-tBu B7 Me CF3
4-tBu B7 Cl Cl
4-tBu B7 CN Me
4-tBu B16 CN Me
4-tBu B3 CN Me
4-tBu 2-(4-tBu—Ph)- CF3 Me
3,3-Me2-cPrC(O)
4-tBu B45 CF3 Me
4-tBuCH2 B3 CF3 Me
4-tBuCH2 B7 Me Me
4-tBuCH2 B16 Me Me
4-tBuCH2 B7 CF3 Me
4-tBuCH2 B8 CF3 Me
4-tBuCH2 B7 Cl Me
4-Et(Me)2C H CF3 Me
4-Et(Me)2C B3 CF3 Me
4-Et(Me)2C B7 CF3 Me
4-Et(Me)2C B8 CF3 Me
4-Et(Me)2C B34 CF3 Me
4-Et(Me)2C B42 CF3 Me
4-Et(Me)2C B16 CF3 Me
4-Et(Me)2C B17 CF3 Me
4-Et(Me)2C H Cl Me
4-Et(Me)2C B7 Cl Me
4-Et(Me)2C B8 Cl Me
4-Et(Me)2C B7 Me CF3
4-Et(Me)2C B7 CN Me
4-Et(Me)2C B4 H Me
4-Et(Me)2C B5 Me Me
4-Et(Me)2C B6 Me Me
4-Et(Me)2C B3 Me Cl
4-Et(Me)2C B16 Me Cl
4-Et(Me)2C B17 Me Cl
4-Et(Me)2C B24 Me Cl
4-nHex B34 CF3 Me
4-nHep B42 CF3 Me
4-nOct B43 Me Me
4-nNon B43 Me Me
4-nDec H Cl Me
4-(Me)2(CN)C B7 Cl Me
4-PhCH2 B7 CF3 Me
4-Ph(Me)2C B7 CF3 Me
4-(4-F—Ph)(Me)2C B7 CN Me
4-MeCH═CH B4 H Me
4-MeCC B5 Cl Me
3-CF3 B6 H Me
4-CF3 B7 OMe Me
4-CF3 B8 SMe Me
4-CF3 B9 SCF3 Me
4-CF3 B16 Me Me
4-CF3 B17 Me Me
4-CF3 B16 Me Me
4-CF3 B17 Cl Me
4-CF3 B7 Cl Me
4-CF3 B7 CF3 Me
4-CF3 B7 Me Me
4-CF3 B3 Cl Me
4-CF3CH2 B7 Me Me
4-Cl2C═CHCH2 B8 Cl Me
4-BrCC B7 Cl Me
4-(2,2-F2)cBuCH2 B7 CF3 Me
4-(1-Me)cPr B16 CN Me
4-cHex B7 CF3 Me
4-(1-Me)cHex B8 CF3 Me
4-MeO B7 CF3 Me
4-iPrO B7 Cl Me
4-iPrO B7 CF3 Me
4-iPrO B15 CF3 Me
4-iPrO B7 Me Me
4-iPrO B16 Me Me
4-iPrO B17 Me Me
4-iPrO B23 SCF3 Me
4-tBuO B7 Me Me
4-tBuO B8 CF3 Me
4-tBuO B7 CF3 Me
4-nHexO B8 CF3 Me
4-nOctO B34 CF3 Me
4-nDecO H CF3 Me
4-CH2═CHCH2O B7 CF3 Me
4-CHCCH2O B8 CF3 Me
4-CHF2O B34 CF3 Me
4-CHF2O B7 Et Me
4-CHF2O B35 Me Me
4-CHF2O B36 Cl Me
4-CHF2O B7 CF3 Me
4-CBrF2O B8 Cl Me
4-CBrF2O B34 Cl Me
4-CBrF2O B40 Me Me
4-CBrF2O B41 Me Me
4-CBrF2O B42 Cl Me
4-CBrF2O B7 CF3 Me
4-CBrF2O B8 CF3 Me
4-CBrF2O COCO2Me CF3 Me
4-CBrF2O H H Me
4-CBrF2O B1 CF3 Me
4-CF3O B2 Cl Me
4-CF3O B3 H Me
4-CF3O B4 OMe Me
4-CF3O B5 SMe Me
4-CF3O B6 SCF3 Me
4-CF3O B7 CF3 Me
4-CF3CH2O B8 Me Me
4-CF2═CHCH2CH2O B9 Me Me
4-CCl2═CHCH2O B10 Cl Me
4-ClCCCH2O B11 Cl Me
4-MeS B12 CF3 Me
4-sBuS H CF3 Me
4-EtSO B3 H Me
4-MeSO2 H CF3 Me
4-MeSO2 B3 CF3 Me
4-MeSO2 B32 CF3 Me
4-MeSO2 B33 CF3 Me
4-EtSO2 H CF3 Me
4-EtSO2 B3 Et Me
4-iPrSO2 B32 CF3 Me
4-iPrSO2 B33 CF3 Me
4-tBuSO2 B7 CF3 Me
4-tBuSO2 B33 CF3 Me
4-MeCH═CHCH2S B15 H Me
4-CH2═CHCH2SO B16 OMe Me
4-CH2═CHCH2SO2 B28 SMe Me
4-CHCCH2S B30 SCF3 Me
4-CHCCH2SO B34 Me Me
4-CHCCH2SO2 CO-nC8H17 Me Me
4-CHF2S H CF3 Me
4-CHF2S B7 CF3 Me
4-CHF2S B8 CF3 Me
4-CHF2S B15 CF3 Me
4-CHF2S B29 CF3 Me
4-CHF2S H Me Me
4-CHF2S B7 Me Me
4-CHF2S B15 Me Me
4-CBrF2S B7 Me CF3
4-CBrF2S B15 Me CF3
4-CBrF2S B30 Me CF3
4-CBrF2S B43 Me CF3
4-CBrF2S CO-nC15H31 nPr Me
4-CBrF2S CO2-nHex CF3 Me
4-CBrF2S H CF3 Me
4-CBrF2S B7 CF3 Me
4-CBrF2S B8 CF3 Me
4-CBrF2S B15 CF3 Me
4-CBrF2S B28 CF3 Me
4-CBrF2S B34 CF3 Me
4-CBrF2S B7 Me Me
4-CF3S CO2-nC10H21 Cl Me
4-CF3S H Me Me
4-CF3S B3 Me Me
4-CF3S B7 Me Me
4-CF3S B8 Me Me
4-CF3S B15 Me Me
4-CF3S H CF3 Me
4-CF3S B7 CF3 Me
4-CF3S B8 CF3 Me
4-CF3S B15 CF3 Me
4-CF3S B34 CF3 Me
4-CF3S CO2-nC12H25 CF3 Me
4-CF3S CO-nC15H31 CF3 Me
4-CF3S CO-nC16H33 Me Me
4-CF3S CO-nC17H35 Me Me
4-CF3CH2S CO-nC18H37 CF3 Me
4-CHF2CF2S CO-nC19H39 CF3 Me
4-CHF2SO CO-nC20H41 Cl Cl
4-CBrF2SO H H Me
4-CBrF2SO B3 CF3 Me
4-CBrF2SO B7 CF3 Me
4-CBrF2SO B24 CF3 Me
4-CBrF2SO B32 CF3 Me
4-CBrF2SO B33 CF3 Me
4-CF3SO H Me Me
4-CF3SO B3 Me Me
4-CF3SO B7 Me Me
4-CF3SO B33 Me Me
4-CF3CH2SO2 B15 H Me
4-CHF2CF2SO2 B16 OMe Me
4-CHF2SO2 B28 SMe Me
4-CHF2SO2 B7 CF3 Me
4-CHF2SO2 B24 CF3 Me
4-CHF2SO2 B32 CF3 Me
4-CHF2SO2 B33 CF3 Me
4-CHF2SO2 H Me Me
4-CHF2SO2 B3 Me Me
4-CHF2SO2 B7 Me Me
4-CHF2SO2 B33 Me Me
4-CBrF2SO2 H SCF3 Me
4-CBrF2SO2 B2 Me Me
4-CBrF2SO2 B3 Me Me
4-CBrF2SO2 B18 Me Me
4-CBrF2SO2 B19 Me Me
4-CBrF2SO2 B33 Me Me
4-CBrF2SO2 H CF3 Me
4-CBrF2SO2 B3 CF3 Me
4-CBrF2SO2 B7 CF3 Me
4-CBrF2SO2 B20 CF3 Me
4-CBrF2SO2 B32 CF3 Me
4-CBrF2SO2 B33 CF3 Me
4-CBrF2SO2 B37 CF3 Me
4-CBrF2SO2 B7 Me CF3
4-CBrF2SO2 B15 Me CF3
4-CBrF2SO2 B17 Me CF3
4-CBrF2SO2 B7 Me CF3
4-CBrF2SO2 B16 Me CF3
4-CF3SO2 B16 Me Me
4-CF3SO2 B7 Cl Me
4-CF3SO2 B15 Cl Cl
4-CF3SO2 B3 CF3 Me
4-CF3SO2 B7 CF3 Me
4-CF3SO2 B15 Me Me
4-CF3SO2 B7 Me Me
4-CF3SO2 B8 Me Me
4-Cl2C═CHCH2S B16 Me Me
4-Cl2C═CHCH2SO B17 Me Me
4-Cl2C═CHCH2SO2 B17 Cl Me
4-CBrCCH2S CO2-nC10H21 Cl Me
4-CBrCCH2SO B33 CF3 Me
4-CBrCCH2SO2 B7 CF3 Me
4-CHO B7 H Me
4-NO2 B8 H Me
4-CN B16 Cl Me
4-(Me)2N B3 H Me
4-Me(MeCO)N B7 OMe Me
4-PhMeN B8 SMe Me
4-PhCH2(MeCO)N B15 SCF3 Me
4-(1-naphthyl) B16 Me Me
4-(2-naphthyl) B28 Me Me
4-(2-Cl—Ph)CH2O B30 Me Me
4-(3-Cl—Ph)CH2O B34 Cl Me
4-(4-Cl—Ph)CH2O B7 CF3 Me
4-(4-Cl—Ph)CH2O B7 Cl Me
4-(4-Cl—Ph)CH2O B37 Cl Me
4-(4-F—Ph)CH2O B42 CF3 Me
4-(2-Me—Ph)CH2O B43 CF3 Me
4-(4-Me—Ph)CH2O B43 CF3 Me
4-(4-Et—Ph)CH2O H CF3 Me
3-(2,4-Cl2—Ph)CH2O B7 CF3 Me
4-(3,4-Cl2—Ph)CH2O B7 H Me
4-(2,5-Me2—Ph)CH2O B7 OMe Me
4-(2,3,4,5,6-F5—Ph)CH2O B7 SMe Me
4-MeOC(O) B4 SCF3 Me
4-EtOC(O) B5 Me Me
4-nPrOC(O) B6 Me Me
4-iPrOC(O) B7 Me Me
4-tBuOC(O) B7 Me Me
4-tBuOC(O) B3 CF3 Me
4-tBuOC(O) B5 CF3 Me
4-tBuOC(O) B33 CF3 Me
4-tBuOC(O) H CF3 Me
4-tBuOC(O) B7 CF3 Me
4-tBuOC(O) B8 CF3 Me
4-tBuOC(O) B34 CF3 Me
4-tBuCH2OC(O) B10 CF3 Me
4-Et(Me)2COC(O) B11 CF3 Me
4-nHexOC(O) B7 H Me
4-MeOCH2 B8 H Me
4-EtOCH2 B7 Cl Me
4-iPrOCH2 B7 H Me
4-MeC(O) B16 OMe Me
4-EtC(O) B7 SMe Me
4-iPrC(O) B8 SCF3 Me
4-tBuC(O) H Cl Cl
4-tBuC(O) B3 Cl Cl
4-tBuC(O) B7 Cl Cl
4-tBuC(O) B3 CF3 Me
4-tBuC(O) B7 CF3 Me
4-tBuC(O) B15 CF3 Me
4-tBuC(O) B7 Me Me
4-tBuC(O) B17 Me Me
4-tBuC(O) B16 Me Me
4-CF3C(O) B33 Me Me
4-CF3CF2C(O) B8 Me Me
4-CF2CF2CF2C(O) B22 Cl Me
4-MeC(O)O B23 Cl Me
4-iPrC(O)O B7 CF3 Me
4-tBuC(O)O B8 CF3 Me
4-CF3C(O)O B7 H Me
4-CF2CF2CF2C(O)O B8 H Me
4-Me2NC(O)O B34 Cl Me
4-Et2NC(O)O H H Me
4-(nPr)2NC(O)O B7 OMe Me
3-Ph B8 SMe Me
4-Ph B34 SCF3 Me
4-(4-F—Ph) B7 Et Me
4-(4-F—Ph) B7 CF3 Me
3-PhO B7 Me Me
3-PhO B15 CF3 Me
4-PhO B7 Me Me
4-(4-F—Ph)O B35 Me Me
4-(4-Cl—Ph)O B36 Et Me
4-(4-Br—Ph)O B7 CF3 Me
4-(4-Me—Ph) B8 CF3 Me
4-(2-Cl—Ph)O B34 CF3 Me
4-(2-F—Ph)O B40 H Me
4-(3-Cl—Ph)O B41 H Me
4-(4-Cl—Ph)O B42 Cl Me
4-(2,4-Cl2—Ph)O B43 H Me
4-(3,4-Cl2—Ph)O B44 OMe Me
4-(3,4,5-Cl3—Ph)O COCO2Me SMe Me
4-(2-Me—Ph)O H SCF3 Me
4-(4-Me—Ph)O B1 Me Me
4-(3-Cl-4-Me—Ph)O B2 H Me
4-(2-pyridyl) B3 H Me
4-(5-CF3-pyridin-2-yl) B4 Cl Me
4-(2-pyridyl)O B7 Me Me
4-(2-pyridyl)O B15 Me Me
4-(2-pyridyl)O B7 CF3 Me
4-(2-pyridyl)O B8 CF3 Me
4-(2-pyridyl)O B34 CF3 Me
4-(2-pyridyl)O B5 CF3 Me
4-(5-CF3-pyridin-2-yl)O B7 Me Me
4-(5-CF3-pyridin-2-yl)O B8 Me Me
4-(5-CF3-pyridin-2-yl)O B15 CF3 Me
4-(5-CF3-pyridin-2-yl)O B7 CF3 Me
4-(5-CF3-pyridin-2-yl)O B15 CF3 Me
4-(5-CF3-pyridin-2-yl)O B34 CF3 Me
4-(3-Cl-5-CF3-pyridin-2-yl) B7 Me Me
4-(3-Cl-5-CF3-pyridin-2-yl) B15 Me Me
4-(3-Cl-5-CF3-pyridin-2-yl) B34 Me Me
4-(3-Cl-5-CF3-pyridin-2-yl) B7 CF3 Me
4-(3-Cl-5-CF3-pyridin-2-yl) B15 CF3 Me
4-(3-Cl-5-CF3-pyridin-2-yl) B17 CF3 Me
4-(3-Cl-5-CF3-pyridin-2-yl) H CF3 Me
4-(5-Cl-thiophen-2-yl) B8 Cl Me
3-OCH2O-4 B9 Cl Me
4-OCF2O-4 B10 CF3 Me
4-MeCH═N B11 CF3 Me
4-Me2C═N B12 CF3 Me
4-MeEtC═N H Cl Me
4-PhCH═N B3 Cl Me
4-PhMeC═N B7 Cl Me
4-PhCH2CH═N B8 CF3 Me
4-cC6H10═N B15 CF3 Me
3-CH2CH2CH2-4 B16 CF3 Me
3-CH2CH2CH2CH2-4 B28 Cl Me
4-PhC(O) H CF3 Me
4-PhC(O) B7 Et Me
4-PhC(O) B7 CF3 Me
4-PhC(O) B33 CF3 Me
4-(2-Cl—Ph)C(O) B7 CF3 Me
4-(4-F—Ph)C(O) H CF3 Me
4-(4-Cl—Ph)C(O) B7 CF3 Me
4-(4-Cl—Ph)C(O) B15 CF3 Me
4-(4-Cl—Ph)C(O) B34 CF3 Me
4-(4-Me—Ph)C(O) B3 CF3 Me
4-(4-Me—Ph)C(O) B16 CF3 Me
4-(3,4-Cl2—Ph)C(O) B45 CF3 Me
2,4-Cl2 B7 CF3 Me
3,4-Cl2 B7 CF3 Me
4-Cl-2-F B7 CF3 Me
3-Cl-4-nHex B7 CF3 Me
4-tBu-3-Cl B7 CF3 Me
4-tBu-3-Cl B15 CF3 Me
3-Cl-4-iPrO B7 Me Me
3-Cl-4-iPrO B7 CF3 Me
3-Cl-4-nHepO B15 CF3 Me
3-Cl-4-(3,4-Cl2—PhCH2)O H CF3 Me
3-Cl-4-PhCH2O B7 CF3 Me
3-Cl-4-Me3CCH2 B7 CF3 Me
3,4-(MeO)2 B7 CF3 Me
4-MeO-3-Me B17 CF3 Me
4-OH-3,5-(tBu)2 B3 CF3 Me
3,4,5-Cl3 B15 CF3 Me
3,5-Cl2-4-F B7 CF3 Me
4-Cl-2,6-F2 B7 CF3 Me
2,6-F2-4-CF3 B7 CF3 Me
2,6-F2-4-CF3O B7 CF3 Me
3,5-Cl2-4-nOct B7 CF3 Me
3,5-Cl2-4-PhCH2O B15 CF3 Me
2,3,5,6-F4-4-Me B3 CF3 Me
2,3,4,5,6-F5 B33 CF3 Me
TABLE 13
Figure USRE038188-20030715-C00346
Figure USRE038188-20030715-C00347
Figure USRE038188-20030715-C00348
Figure USRE038188-20030715-C00349
Figure USRE038188-20030715-C00350
Figure USRE038188-20030715-C00351
Figure USRE038188-20030715-C00352
Figure USRE038188-20030715-C00353
Figure USRE038188-20030715-C00354
Figure USRE038188-20030715-C00355
Figure USRE038188-20030715-C00356
Figure USRE038188-20030715-C00357
Figure USRE038188-20030715-C00358
Figure USRE038188-20030715-C00359
Figure USRE038188-20030715-C00360
Figure USRE038188-20030715-C00361
Figure USRE038188-20030715-C00362
Figure USRE038188-20030715-C00363
Figure USRE038188-20030715-C00364
Figure USRE038188-20030715-C00365
Figure USRE038188-20030715-C00366
Figure USRE038188-20030715-C00367
R1 B A
iPr H 2,5-Me2-1-pyrrolyl
iPr B3 1-Me-2-pyrrolyl
tBu B5 3,5-Me2-2-pyrrolyl
tBu B6 3,4-Me2-2-pyrrolyl
tBu B7 3,4,5-Me3-2-pyrrolyl
1-Me-cPr B8 3,5-Me2-4-MeO-2-pyrrolyl
1-Me-cPr B15 4-MeC(O)-3,5-Me2-2-pyrrolyl
1-Me-cPr B16 4-NO2-2-pyrrolyl
1-Me-cPr B17 2-Me-3-pyrrolyl
1-Me-cHex B22 4-Me-3-pyrrolyl
1-Me-cHex B31 2,4,5-Me3-3-pyrrolyl
1-Me-cHex B32 2,4-Me2-5-EtO2C-3-pyrrolyl
1-Me-cHex B33 1,2,3-triazol-4-yl
PhCH2 B34 1-Me-1,2,3-triazol-4-yl
PhCH2 B35 2-Me-1,2,3-triazol-4-yl
PhCH2 B36 3-Me-1,2,3-triazol-4-yl
PhMe2C B40 2-EtO2C-1,2,3-triazol-4-yl
PhMe2C B41 5-Me-2-Ph-1,2,3-triazol-4-yl
PhMe2C pyridin-2-yl-C(O) 5-CF3-2-Me-1,2,3-triazol-4-yl
PhMe2C pyridin-2-yl-C(O) 2,5-Me2-1,2,3-triazol-4-yl
Ph pyridin-2-yl-C(O) 1-PhCH2-5-Me-1,2,3-triazol-4-yl
2-F—Ph H 1-PhCH2-5-CF3-1,2,3-triazol-4-yl
2-F—Ph B3 1-PhCH2-5-Cl-1,2,3-triazol-4-yl
2-F—Ph B5 4-Me-1,2,3-triazol-1-yl
2-F—Ph B6 5-Me-1,2,3-triazol-2-yl
2-Cl—Ph B7 4-MeO2C-1,2,3-triazol-1-yl
2-Cl—Ph B8 4,5-EtO2C-1,2,3-triazol-2-yl
2-Cl—Ph B15 4,5-Me2-1,2,3-triazol-1-yl
2-Me—Ph B16 4,5-(MeO2C)2-1,2,3-triazol-2-yl
2-Me—Ph B17 4,5-Me2-1,2,4-triazol-3-yl
2-Me—Ph B22 2,4-Me2-1,2,4-triazol-3-yl
4-NO2—Ph B31 1,5-Me2-1,2,4-triazol-3-yl
2,6-F2—Ph B32 5-Me-3-CF3-1,2,4-triazol-2-yl
2,6-F2—Ph B33 3-Cl-5-CF3-1,2,4-triazol-2-yl
2,6-F2—Ph B34 5-Cl-3-CF3-1,2,4-triazol-2-yl
2,6-F2—Ph B35 3,5-Me31,2,4-triazol-4-yl
2,6-F2—Ph B36 3,5-Cl2-1,2,4-triazol-4-yl
2,6-Cl2—Ph B40 3,5-(CF3)2-1,2,4-triazol-4-yl
2,6-Cl2—Ph B41 5-tetrazolyl
2,6-Cl2—Ph pyridin-2-yl-C(O) 5-Ph-1-tetrazolyl
2,6-Cl2—Ph pyridin-2-yl-C(O) 5-Ph-2-tetrazolyl
2-pyridyl pyridin-2-yl-C(O) 3,4,4,5-Me4-2-pyrazolin-1-yl
2-pyridyl B8 3-Me-5-CF3-2-pyrazolin-1-yl
2-pyridyl B15 1,5-Me2-3-CF3-2-pyrazolin-4-yl
2-pyridyl B16 1,4-Me2-3-Ph-2-pyrazolin-4-yl
2-pyridyl B17 1,4-Me2-5-Ph-2-pyrazolin-4-yl
2-pyridyl B22 1,3-Me2-2-pyrazolin-5-yl
1-naphthyl B31 1,5-Me2-2-pyrazolin-3-yl
1-naphthyl B32 2-Me-2-imizolin-1-yl
1-naphthyl B33 2-CF3-2-imizolin-1-yl
iPr B34 2-MeS-2-imizolin-1-yl
iPr B35 2-MeO-2-imizolin-1-yl
tBu B36 5-Me-2-Ph-2-oxazolin-4-yl
1-Me-cPr B40 2,5-Me2-2-oxazolin-4-yl
cHex B41 5-Me-2-CF3-2-oxazolin-4-yl
1-Me-cHex pyridin-2-yl-C(O) 2-thiazolin-2-yl
PhCH2 pyridin-2-yl-C(O) 2-Me2N-2-thiazolin-4-yl
PhMe2C pyridin-2-yl-C(O) 2,4-Me2-2-thiazolin-5-yl
Ph B8 2-Me-4-CF3-2-thiazolin-5-yl
2-F—Ph B15 5-Me-2-isoxazolin-3-yl
2-Cl—Ph B16 3-Cl-5-Me-2-isoxazolin-4-yl
2-Me—Ph B17 3,5-(MeS)2-2-isothiazolin-4-yl
4-NO2—Ph B22 5-Cl-2-Me-3(2H)-pyridazinon-4-yl
2,6-F2—Ph B31 5,6-Cl2-2-Me-pyridazinon-4-yl
2,6-Cl2—Ph B32 4-Cl-2-Me-pyridazinon-4-yl
2-pyridyl B33 4,6-Cl2-2-Me-pyridazinon-4-yl
1-naphthyl B34 4,5-Cl2-2-Me-pyridazinon-4-yl
TABLE 14
Figure USRE038188-20030715-C00368
Figure USRE038188-20030715-C00369
Figure USRE038188-20030715-C00370
Figure USRE038188-20030715-C00371
Figure USRE038188-20030715-C00372
Figure USRE038188-20030715-C00373
Figure USRE038188-20030715-C00374
Figure USRE038188-20030715-C00375
Figure USRE038188-20030715-C00376
Figure USRE038188-20030715-C00377
Figure USRE038188-20030715-C00378
Figure USRE038188-20030715-C00379
R1 E B A
tBu oxazol-2-yl H A1
tBu thiazol-2-yl B3 A2
tBu imidazol-2-yl B7 A3
tBu 1,5-Me2-1,2,4-triazol-3-yl B8 A4
tBu 5-Me-1,2,4-oxadiazol-3-yl B15 A5
tBu 5-CF3-1,2,4-thiadiazol-3-yl B16 A6
tBu 5-Me-1,3,4-oxadiazol-2-yl B17 A7
tBu tetrazol-5-yl B18 A8
tBu 2-oxazolin-2-yl B32 A9
tBu 1,2,4,5-tetrazin-3-yl B33 A10
tBu F B34 A11
tBu Cl H A12
tBu Br B7 A13
tBu I B8 A14
tBu CHC H A15
tBu CHC B7 A2
2,6-F2—Ph CHC B7 A2
tBu MeCC B7 A16
tBu EtCC B7 A17
tBu PhCC B7 A2
tBu PhCC B8 A13
2,6-F2—Ph PhCC H A2
2,6-F2—Ph PhCC B7 A2
pyridin-2-yl PhCC B7 A2
tBu (2-Cl—Ph)CC B15 A19
tBu (3-Cl—Ph)CC B15 A20
2,6-F2—Ph (4-Cl—Ph)CC B16 A21
2,6-F2—Ph (4-F—Ph)CC B17 A22
2,6-F2—Ph (4-Me—Ph)CC B18 A23
2,6-F2—Ph (4-nHex-Ph)CC B34 A24
2,6-F2—Ph (2,6-Cl2—Ph)CC H A25
2,6-F2—Ph (2,4-Cl2—Ph)CC (EtO)2P(S) A26
2,6-F2—Ph (3,4-Cl2—Ph)CC B3 A27
2,6-F2—Ph (2,4,6-Me3—Ph)CC B7 A28
2,6-F2—Ph (4-CF3—Ph)CC B15 A29
2,6-F2—Ph CF3 B7 A2
2,6-F2—Ph CF3CF2 H A31
2,6-F2—Ph NO2 B3 A32
2,6-F2—Ph N3 B7 A33
2,6-F2—Ph N3 H A2
2,6-F2—Ph N3 B7 A1
tBu N3 B7 A2
tBu N3 H A2
pyridin-2-yl N3 B7 A2
2,6-F2—Ph CHO B8 A34
2,6-F2—Ph C(O)Me B15 A35
2,6-F2—Ph C(O)Et B16 A36
2,6-F2—Ph C(O)iPr B17 A1
2,6-F2—Ph C(O)nBu B18 A2
2,6-F2—Ph C(O)sBu B32 A3
2,6-F2—Ph C(O)tBu H A2
2,6-F2—Ph C(O)tBu H A1
2,6-F2—Ph C(O)tBu B7 A1
tBu C(O)tBu H A2
tBu C(O)tBu B7 A2
tBu CO2Me H A2
tBu CO2Me B7 A2
tBu CO2Me B8 A2
2,6-F2—Ph CO2Me H A2
2,6-F2—Ph CO2Me B7 A2
2,6-F2—Ph CO2Me B8 A2
pyridin-2-yl CO2Me H A2
pyridin-2-yl CO2Me B7 A2
pyridin-2-yl CO2Me B8 A2
tBu CO2Me B34 A5
tBu CO2Et H A2
tBu CO2Et B7 A2
tBu CO2Et B8 A2
2,6-F2—Ph CO2Et H A2
2,6-F2—Ph CO2Et B7 A2
2,6-F2—Ph CO2Et B8 A2
pyridin-2-yl CO2Et H A2
pyridin-2-yl CO2Et B7 A2
pyridin-2-yl CO2Et B8 A2
pyridin-2-yl CO2Et H A6
pyridin-2-yl CO2nPr B7 A7
pyridin-2-yl CO2iPr B8 A8
pyridin-2-yl CO2nBu H A9
pyridin-2-yl CO2iBu B7 A10
pyridin-2-yl CO2sBu B7 A11
pyridin-2-yl CO2tBu B8 A12
pyridin-2-yl CO2CH2CH═CH2 B15 A13
pyridin-2-yl CO2CH2CH═CH2 B7 A2
tBu CO2CH2CH═CH2 B8 A2
tBu CO2CH2CH═CH2 H A2
tBu CO2CH2CH═CH2 B7 A2
2,6-F2—Ph CO2CH2CH═CH2 B8 A2
2,6-F2—Ph CO2CH2CH═CH2 H A2
2,6-F2—Ph CO2CH2CH═CH2 B7 A2
pyridin-2-yl C(O)NHMe B8 A2
2,6-F2—Ph C(O)NHMe H A2
tBu C(O)NHMe H A2
pyridin-2-yl C(O)NHEt B16 A15
pyridin-2-yl C(O)NHnPr B17 A16
tBu C(O)NHiPr B18 A17
tBu C(O)NHiBu B34 A18
tBu C(O)NHtBu H A19
tBu C(O)NMe2 (EtO)2P(S) A20
tBu C(O)NMe2 H A2
tBu C(O)NMe2 B7 A2
2,6-F2—Ph C(O)NMe2 B7 A2
pyridin-4-yl C(O)NMeEt B3 A21
2,6-F2—Ph C(O)NEt2 B7 A22
tBu C(O)N(nPr)2 B15 A23
tBu PhC(O) H A24
tBu PhC(O) H A2
tBu PhC(O) B7 A2
tBu PhC(O) B8 A2
2,6-F2—Ph PhC(O) H A2
2,6-F2—Ph PhC(O) B7 A2
2,6-F2—Ph PhC(O) B8 A2
pyridin-2-yl PhC(O) H A2
pyridin-2-yl PhC(O) B7 A2
2,6-F2—Ph (4-F—Ph)C(O) B8 A2
2,6-F2—Ph (3,4-Cl2—Ph)C(O) H A6
pyridin-3-yl (3-Cl-4-F—Ph)C(O) B8 A27
pyridin-3-yl (4-Me—Ph)C(O) B15 A28
tBu C(S)NH2 B16 A29
tBu C(S)NH2 H A2
tBu C(S)NH2 B7 A2
2,6-F2—Ph C(S)NH2 B8 A2
2,6-F2—Ph C(S)NH2 H A2
2,6-F2—Ph C(S)NH2 B7 A2
pyridin-2-yl C(S)NH2 B8 A2
pyridin-2-yl C(S)NH2 H A2
2,6-F2—Ph MeS B7 A2
2,6-F2—Ph EtS B18 A31
pyridin-2-yl nPrS B32 A32
pyridin-2-yl tBuS B33 A33
tBu MeSO B34 A34
tBu EtSO H A35
tBu nPrSO B7 A36
2,6-F2—Ph tBuSO B8 A1
2,6-F2—Ph MeSO2 H A2
2,6-F2—Ph EtSO2 B7 A3
pyridin-2-yl iPrSO2 B7 A4
pyridin-2-yl nBuSO2 B8 A5
tBu PhS B15 A6
tBu PhS H A2
tBu PhS B7 A2
2,6-F2—Ph PhS B8 A2
2,6-F2—Ph PhS H A2
2,6-F2—Ph PhS B7 A2
pyridin-2-yl PhS B8 A2
pyridin-2-yl PhS H A2
pyridin-2-yl PhS B7 A2
tBu (4-Me—Ph)S B8 A2
tBu (4-Cl—Ph)SO H A6
tBu (2-F—Ph)SO2 B17 A9
2,6-F2—Ph (MeO)2P(O) B18 A10
2,6-F2—Ph (EtO)2P(O) B34 A11
2,6-F2—Ph (nPrO)2P(O) H A12
pyridin-2-yl (PhO)(MeO)P(O) (EtO)2P(S) A13
pyridin-2-yl (MeO)2P(S) B3 A14
tBu (EtO)2P(S) B7 A15
tBu (nPrO)2P(S) B15 A16
tBu (PhO)(MeO)P(S) B7 A17
Where the compounds of the present invention are used as pesticides, in general, they can be mixed with a suitable carrier, for example a solid carrier, such as clay, talc, bentonite, diatomaceous earth or white carbon, or a liquid carrier such as water, alcohols (e.g., isopropanol, butanol, benzyl alcohol, furfuryl alcohol), aromatic hydrocarbons (e.g., toluene, xylene), ethers (e.g., anisole), ketones (e.g., cyclohexanone, isophorone), esters (e.g., butyl acetate), acid amides (e.g., N-methylpyrrolidone) or halogenated hydrocarbons (e.g., chlorobenzene), optionally along with other additives such as surfactant, emulsifier, dispersing agent, penetrating agent, spreading agent, thickener, anti-freezing agent, anti-caking agent and stabilizer, and can be formulated into any desired forms for practical use, such as liquid preparations, emulsions, wettable powders, dry flowables, flowables, dusts and granules.
Where the compounds of the present invention are used as agricultural chemicals, they can be combined with any other herbicides, various insecticides, acaricides, nematecides, fungicides, plant growth regulators, synergists, fertilizer and soil improvers, when they are formulated into preparations for practical use or while they are actually used through spraying or the like.
In particular, the combination of the compounds of the invention and other agricultural chemicals or plant hormones will be advantageous in that the amount of the chemicals to be used can be reduced thereby resulting in the reduction of the costs for the treatment, and that the mixed chemicals exhibit synergistic effects to broaden the insecticidal spectrum while displaying higher pesticidal activities. If desired, the compounds of the invention can be combined with e plurality of known agricultural chemicals. For the agricultural chemicals capable of being combined with the compounds of the invention, for example, the compounds described in Farm Chemicals Handbook, 1994 are referred.
Their concrete general names are raised below. However, the present invention is not necessarily limited by them.
Fungicide: acibenzolar, ampropyfos, anilazine, azaconezole, azoxystrobin, benalaxyl, benodanil, benomyl, benzamecril, binapacryl, biphenyl, bitertanol, bethoxazine, Bordeaux mixture, blesticidin-S, bromoconazole, bupirimate, buthiobate, calcium polysulfide, captafol, captan, copper oxychloride, caryropamid, carbendazim, carboxin, chinomethionat, chlobrnthiazone, chlorfenazol, chloroneb, chlorothalonil, chlozolinete, cufraneb, cymoxanil, cyproconazol, cyprodinil, cyprofuram, debacarb, dichlorophen, diclobutrazol, dichlofluanid, diclomezine, dicloran, diethofencarb, diclocymet, difenoconazole, diflumetorim, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, famoxadone, fenarimol, febuconazole, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriefol, folpet, fosetyl-aluminium, fuberidazole, furalaxyl, fenamidone, fenhexamid, guazatine, hexechlorobenzene, hexaconazole, hymexazol, imazalil, imibenconazole, iminoctedine, ipconazole, iprobenfos, iprodione, isoprothiolane, iprovalicarb, kasugamycin, kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, metiram, metominostrobin, myclobutenil, nabam, nickel bis (dimethyldithiocarbamate), nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oxadixyl, oxycarboxin, oxpoconazole fumarate, pefuaoate, penconazole, pencycuron, phthalide, piperalin, polyoxins, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quinoxyfen, quintozene, sulfur, spiroxamine, tebuconazole, tecnazene, tetreconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, toriadimenol, triazoxide, tricyclezole, tridemorph, triflumizole, triforine, triticonazole, validamycin, vinclozolin, zineb, ziram.
Bacteriazide: streptomycin, oxyterracycline, oxolinic acid.
Nematicide: aldoxycarb, cadusafos, fosthiazate, fosthietan, oxemyl, fenamiphos.
Acaricide: acequinocyl, acrinathrin, amitraz, bifenazate, bromopropylate, chinomethionat, chlorobezilate, clofentezine, cyhexatine, dicofol, dirnochlor, etoxazole, frnazaquin, fenbutatin oxide, fenpropathrin, fenproximate, halfenprox, hexythiazox, milbemectin, phenisobromolate, polynactins, propargite, pyridaben, pyrimidifen, tebufenpyrad, tetradifon.
Insecticide: abamectin, acephate, ecetamipirid, alanycarb, azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin, Batillus thuringiensis, buprofezin, butocarboxim, carberyl, carbofuran, carbosulfan, cartap, chlorfenapyr, chlorpyrifos, chlorfenvinphos, chlorfluazuron, clothianidin, chromafenozide, chlorpyrifos-methyl, cyanox, cycloprothrin, cyfluthrin, beta-cyfluthrin, cypermethrin, cyromezine, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diecloden, dichlorvos, diflubenzuron, dimethylvinphos, diofenolan, disulfoton, dimethoate, emamectin-benzoate, EPN, esfenvalerate, ethiofencarb, endosulfan, ethiprole, ethylthiometone, etofenprox, etrimfos, fenitrothion, fenobucarb, fenothiocarb, fenthion, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flucythrinate, flufenoxuron, flufenprox, tau-fluvalinate, fonophos, formetenate, formothion, furathiocerb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocerb, isoxathion, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methacrifos, metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide, monocrotophos, muscalure, nicotin-sulfate, nitenpyram, omethoate, oxydemeton-methyl, oxamyl, parathion, parathion-methyl, permethrin, phenthoete, phoxim, phorate, phosalone, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, propafos, prothiofos, pymetrozine, pyraclofos, pyridafenthion, pyriproxyfen, rotenone, sulprofos, silafluofen, spinosad, sulfotep, tebfenozide, teflubenzuron, tefluthorin, terbufos, tetrachlorvinphos, thiodicarb, thiamethoxam, thiocyclam, thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, vamidothion.
The dose of the compounds of the present invention varies depending on an application place, an application time, an application method, cultivation crops, etc. In general, it may be between approximately 0.005 kg and 50 kg per hectare (ba) in terms of the amount of the active ingredient.
Now, formulation examples comprising the compounds of the invention are mentioned below, which, however, are not intended to restrict the scope of the invention. In the following formulation examples, “part” or “parts” are by weight.
[Wettable Powders]
Compound of the invention 5 to 80 parts
Solid carrier 10 to 85 parts
Surfactant 1 to 10 parts
Others 1 to 5 parts
The others include, for example, anti-caking agent, etc.
[Emulsions]
Compound of the invention 1 to 30 parts
Liquid carrier 30 to 95 parts
Surfactant 5 to 15 parts
[Flowables]
Compound of the invention 5 to 70 parts
Liquid carrier 15 to 65 parts
Surfactant 5 to 12 parts
Others 5 to 30 parts
The others include, for example, anti-freezing agent, thickener, etc.
[Dry Flowables (wettable granules)]
Compound of the invention 20 to 90 parts
Solid carrier 10 to 60 parts
Surfactants 1 to 20 parts
[Granules]
Compound of the invention 0.1 to 10 parts
Solid carrier 90 to 99.99 parts
Others 1 to 5 parts
[Dusts]
Compound of the invention 0.01 to 30 parts
Solid carrier 67 to 99.5 parts
Others 0 to 3 parts
Where the compounds of the present invention are used as an agent for preventing the attachment of aquatic organisms, they may be formulated into various preparations of, for example, coating paints, solutions, emulsions, pellets or flakes to be applicable to various objects. Depending on the application place, the object and the form, the preparations can be used in any ordinary manners of, for example, coating, spraying, dipping, adding to water or installing in water. To prepare such coating paints, solutions, emulsions and others, employable are any ordinary methods. Apart from the above-mentioned preparations and modes of using the compounds of the present invention, the compounds may also be used, for example, by incorporating them into ropes or fiber materials for fishing nets in the stage of preparing the ropes or fiber materials to thereby making them have the ability to prevent the attachment of aquatic organisms thereto. The agents for preventing the attachment of aquatic organisms according to the present invention can be used either singly or as combined with any other agents for preventing the attachment of aquatic organisms.
Where the aquatic adhesion inhibitors of the invention are used in the form of antifouling coatings, for example, the compounds of the invention may be mixed with film-forming agents to prepare coatings. The film-forming agents include oil varnishes, synthetic resins, artificial rubbers, etc. If desired, solvents, pigments and others can be added to the coatings. To prepare the paints, the uppermost limit of the concentration of the compounds of the invention to be therein is not specifically limited, provided that the resulting coatings can form film, but may be from 1 to 50% by weight, preferably from 5 to 20% by weight, relative to the weight of the antifouling coatings.
Where the agents for preventing the attachment of aquatic organisms of the present invention are used in the form of solutions, for example, the compounds of the invention may be dissolved in solvents along with film-forming agents to prepare solutions. The film-forming agents include synthetic resins, artificial rubbers, natural resins, etc. The solvents include xylene, toluene, cumene, methyl ethyl ketone, methyl isobutyl ketone, acetone, etc. If desired, additives such as plasticizer may be added to the solutions. To prepare the solutions, the uppermost limit of the concentration of the compounds of the invention to be therein is not specifically limited, provided that the compounds are dissolved to give solutions, but may be from 1 to 50% by weight, preferably from 5 to 30% by weight, relative to the weight of the solutions.
Where the agents for preventing the attachment of aquatic organisms of the present invention are used in the form of emulsions, surfactants are added to the compounds of the invention to prepare the intended emulsions according to ordinary methods of preparing general emulsions. In this, the type of the surfactants to be used is not specifically limited. To prepare the emulsions, the uppermost limit of the concentration of the compounds of the invention to be therein is not specifically limited, provided that the compounds are emulsified to give emulsions, but may be from 1 to 50% by weight, preferably from 5 to 30% by weight, relative to the weight of the emulsions.
Where the agents for preventing the attachment of aquatic organisms of the present invention are used in the form of pellets or flakes, for example, the constitutive components of the compounds of the invention and optionally plasticizers, surfactants and others are added to the base of hydrophilic resins which are solid at room temperature, such as polyethylene glycol in a solid form, and the resulting mixtures are shaped into pellets or flakes through melting molding, compression molding or the like. To prepare the pellets or flakes, the uppermost limit of the concentration of the compounds to be therein is not specifically limited, provided that the compounds can be shaped into pellets or flakes, but may be from 20 to 95% by weight, preferably from 30 to 90% by weight, relative to the weight of the pellets or flakes.
EXAMPLES
The present invention is illustrated specifically by referring to the following Synthesis Examples, Formulation Examples and Test Examples, which, however, are not intended to restrict the scope of the invention.
Synthesis Example 1 Synthesis of 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile (Compound No. I-40)
1) 3.0 g of 3-(2,6-difluorophenyl)pyrazole was dissolved in 20 ml of acetonitrile, and 2.52 g of chloroacetonitrile and 4.61 g of potassium carbonate were added thereto at room temperature, and heated under reflux for 5 hours. After acetonitrile was distilled off under reduced pressure, ethyl acetate was added to the residue, which was then washed with a small amount of water. The organic layer was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was recrystallized from a mixed solvent to isopropylether and diethyl ether to obtain 1.74 g of 1-cyanomethyl-3-(2,6-difluorophenyl) pyrazole.
2) A solution of 0.5 g of 1-cyanomethyl-3-(2,6-difluorophenyl)pyrazole dissolved in 10 ml of THF was dropwise added to a suspension of 0.15 g of 55% sodium hydride in 10 ml of THF, at 50° C. After the resulting product was stirred for 30 minutes, a solution of 0.67 g of 1-(1-methyl-3,5-dichloropyrazole-4-carbonyl)pyrazole dissolved in 10 ml of THF was dropwise added thereto at 50° C. and then stirred overnight at room temperature. The reaction mixture was poured into water, then extracted with ethyl acetate and washed with a small amount of water. The resulting product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was recrystallized from a mixed solvent of isopropyl ether/ethyl acetate=3/1 to obtain 0.52 g of 2-{3-(2,6-diflyuorophenyl)pyrazol-1-yl}-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile.
Synthesis Example 2 Synthesis of 3-(1-methyl-3,5-dichloropyrazol-4-yl)-2-(2-phenylthiazol-4-yl)-3-hydroxyacrylonitrile (Compound No. II-1)
1) 2.33 g of thiobenzamide was dissolved in 20 ml of dry methanol, and 2.16 g of 1,3-dichloroacetone was added thereto at room temperature and then heated under reflux for 1 hour. The solvent was distilled off under reduced pressure, and ice water was added to the remaining product, which was then neutralized with an aqueous solution of sodium hydrogen carbonate. The resulting product was extracted with ethyl acetate, washed with saturated saline, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 2.03 g of 4-chloromethyl-2-phenylthiazole was obtained from the fraction eluted with chloroform/n-hexane=1/2.
2) 1.39 g of 4-chloromethyl-2-phenylthiazole was dissolved in 10 ml of acetonitrile, and 0.65 g of potassium cyanide and 0.05 g of dibenzo-18-crown-6-ether were added thereto at room temperature, and then heated under reflux for 10 hours. After the temperature was returned to room temperature, ethyl acetate was added the resulting mixture, and the insoluble solid was removed through filtration. The resulting ethyl acetate solution was washed with saturated saline and water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 0.98 g of 4-cyanomethyl-2-phenylthiazole from the fraction eluted with chloroform.
3) 0.72 g of 4-cyanomethyl-2-phenylthiazole was dissolved in 10 ml of dry THF, and 4.6 ml of n-butyl lithium (1.56 M hexane solution) was dropwise added thereto at −60° C. or lower in an argon atmosphere. After the resulting product was stirred at −60° C. or lower for 20 minutes, 0.84 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride as dissolved in 3 ml of dry THF was dropwise added thereto at −60° C. or lower. Then, the resulting product was gradually heated, and stirred for 4 hours at room temperature. The reaction mixture was poured into ice water, acidified with diluted hydrochloric acid, extracted with ethyl acetate, and washed with saturated saline. The resulting product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain the intended product from the fraction eluted with chloroform. The resulting product was crystallized and washed with diethyl ether to obtain 0.86 g of 3-(1-methyl-3,5-dichloropyrazol-4-yl)-2-(2-phenylthiazol-4-yl)-3-hydroxyacrylonitrile.
Synthesis Example 3 Synthesis of 3-(1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)-2-(4-tert-butylthiazol-2-yl)-3-pivaloyloxyacrylonitrile (Compound No. III-6, III-15)
0.5 g of 3-(1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)-2-(4-tert-butylthiazol-2-yl)-3-hydroxyacrylonitrile and 0.14 g of triethylamine were added to 15 ml of THF at room temperature and stirred to give a uniform solution. 0.16 g of pivaloyl chloride was dropwise added to the solution with cooling with ice, then gradually heated, and stirred at room temperature for 8 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate, and washed thrice with saturated saline. After having been dried over sodium sulfate, the resulting product was passed through a short column filled with silica gel. The solvent was distilled off under reduced pressure, and the residual product was applied to silica gel thin-layer chromatography (developer solvent: chloroform) to obtain 0.16 g of 3-(1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)-2-(4-tert-butylthiazol-2-yl)-3-pivaloyloxyacrylonitrile (III-6) and 0.35 g of its geometric isomer (III-15).
Compound No. III-6
1H-NMR (CDCl3, δ ppm); 1.18 (9H, s), 1.32 (9H, s), 3.85 (3H, s), 6.88 (1H, s)
Compound No. III-15
1H-NMR (CDCl3, δ ppm); 1.33 (9H, s), 1.39 (9H, s), 3.94 (3H, s), 7.03 (1H, s)
Reference Example Synthesis of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carboxylic acid
1) 21.35 g of phosphorus oxychloride was dropwise added to 4.72 g of DMF at 10° C. or lower. After the temperature of the reaction solution was returned to room temperature, the reaction mixture was stirred for 1 hour, and 10.71 g of 1-methyl-3-trifluoromethyl-5-pyrazolone was added thereto. The resulting mixture was heated up to 110° C., and stirred for 7 hours. After having been left to be at 70° C. the reaction mixture was poured into ice water. After pH of the mixture was made to be about 4 with an aqueous solution of sodium hydroxide added thereto, and precipitated crystals were taken out through filtration and dried to obtain 10.55 g of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carbaldehyde.
2) 8.88 g of 1-methyl-3-2-(tert-trifluoromethyl-5-chloropyrazole-4-carbaldehyde and 7.24 g of potassium permanganate were added to an aqueous solution of 0.23 g of potassium hydroxide in 85 ml of water, at room temperature. After having been heated up to 60° C., the resulting mixture was stirred for 2 hours. Next, the temperature of the mixture was return to room temperature, and the solid was removed through filtration. The resulting filtrate was acidified with an aqueous solution of hydrochloric acid, and precipitated crystals were taken out through filtration, washed with water, and dried. The thus-obtained crystals were added to 150 ml of chloroform, and heated under reflux, and the insoluble solid was removed through filtration at a heating time. Chloroform was distilled off under reduced pressure, and 6.24 g of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carboxylic acid was obtained.
Synthesis Example 4 Synthesis of 2-(2-tert-butylthiazol-4-yl)-3-(2-methyl-4-trifluoromethylthiazol-5-yl)-3-benzoyloxyacrylonitrile (Compound No. II-75)
In the same manner as above, the above-mentioned compound was synthesized (viscous liquid, E-Z mixture).
1H-NMR (CDCl3, δ ppm); 1.09 (9H, s), 2.75 (3H, s), 7.3-7.6 (4H, m), 8.05-8.25 (2H, m): major 1.19 (9H, s), 2.70 (3H, s), 7.3-7.6 (4H, m), 8.05-8.25 (2H, m): minor
Synthesis Example 5 Synthesis of 2-(4-trifluoromethylphenyl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-(1-methyl-3,5-dichloropyrazole-4-carbonyloxy)acrylonitrile (Compound No. IV-5)
1.0 g of 4-(trifluoromethyl)phenylacetonitrile and 2.31 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride were dissolved in 30 ml of dry THF, and 0.61 g of potassium t-butoxide was added thereto at room temperature. After having been heated, the resulting product was kept heated under reflux for 3 hours. 0.61 g of potassium t-butoxide was again added thereto and further heated under reflux for 2 hours. THF was distilled off under reduced pressure, and water was added to the residual product, which was then extracted with ethyl acetate. The resulting organic layer was washed with a dilute aqueous solution of sodium hydroxide and then with water. This was dried with sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography to obtain 1.92 g of 3-(1-methyl-3,5-dichlorophrazol-4-yl)-2-(4-trifluoromethylphenyl)-3-(1-methyl-3,5-dichloropyrazole-4-carbonyloxy)acrylontrile from the fraction eluted with n-hexane:ethyl acetate=2:1.
Synthesis Example 6 Synthesis of 2-(4-tert-butylphenyl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylontrile (Compound No. IV-18)
0.22 g of dibenzo-18-crown-6-ether and 1.57 g of sodium cyanide were suspended in 20 ml of DMSO, and 5.00 g of 4-tert-butylbenzyl bromide was dropwise added thereto with cooling with water. After having been stirred overnight at room temperature, the resulting mixture was further stirred at 50° C. for 5 hours. After this was left to be at room temperature, water was added thereto and extracted with ether. The organic layer was washed with water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 1.19 g of 4-tert-butylphenylacetonitrile was obtained from the fraction eluted with n-hexane:ethyl acetate 5:1.
1.00 g of 4-tert-butylphenylacetonitrile and 1.23 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride were dissolved in 20 ml of THF, and 1.01 g of potassium t-butoxide was added thereto with cooling with ice. After the resulting mixture was stirred overnight at room temperature, water was added thereto, acidified with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and dried with sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was dissolved in a mixed solvent of 10 ml of water and 10 ml of dioxane, and 0.38 g of potassium hydroxide was added thereto and heated under reflux for 4 hours. After having been left to be at room temperature, this was acidified with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 0.64 g of 2-(4-tert-butylphenyl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile from the fraction eluted with n-hexane:ethyl acetate=2:1.
Synthesis Example 7 Synthesis of 2-(4-tert-butylphenyl)-3-(1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)-3-pivaloyloxyacrylonitrile (Compound No. IV-24)
In the same manner as above, the above-mentioned compound was synthesized (viscous liquid).
1H-NMR (CDCl3, δ ppm); 1.13 (9H, s), 1.33 (9H, s), 3.98 (3H, s), 7.48 (4H, brs)
Synthesis Example 8 Synthesis of 2-(4-tert-butylphenyl)-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-methoxycarbonyloxyacrylonitrile (Compound No. IV-36)
In the same manner as above, the above-mentioned compound was synthesized (vitreous, E-Z mixture).
1H-NMR (CDCl3, δ ppm); 1.32 (9H, s), 3.75 (3H, s), 3.87 (3H, s), 7.49 (2H, d, J=8 Hz), 7.58 (2H, d, J=8 Hz): 75% 1.27 (9H, s), 3.88 (3H, s), 3.96 (3H, s), 7.49 (2H, d, J=8 Hz), 7.58(2H, d, J=8 Hz): 25%
Synthesis Example 9 Synthesis of 2-{2-tert-butyloxazol-4-yl}-3-(3,5-dichloro-1-methyl-pyrazol-4-yl)-3-hydroxyacrylonitrile (Compound No. V-40)
1) 25 g of pivalic acid amide and 25 g of 1,3-dichloro-2-propanone were mixed and heated on an oil bath at 135° C. for 2.5 hours. After having been cooled with ice, the mixture was made alkaline with an aqueous solution of sodium hydroxide added thereto. Then, the resulting product was extracted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through column chromatography (silica gel; ethyl acetate n-hexane=1:8) to obtain 17.5 g of 2-tert-butyl-4-chloromethyloxazole.
2) 6.2 g of sodium cyanide was weighed, 50 ml of dimethylsulfoxide was added thereto, and a dimethylsulfoxide solution of 16.9 g of 2-tert-butyl-4-chloromethyloxazole was dropwise added thereto, and heated on an oil bath at 65° C. for 1 hour with stirring. After the resulting product was cooled to room temperature, 150 ml of a dilute aqueous solution of sodium hydroxide was added thereto, and extracted with toluene. The organic layer was fully washed with water, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 14.8 g of 2-tert-butyl-4-cyanomethyloxazole.
3) 2.87 g of potassium tert-butoxide was suspended in 20 ml of THF, and a solution of 2.00 g of 2-tert-butyl-4-cyanomethyloxazole and 2.37 g of 3,5-dichloro-1-methylpyrazole-4-carbonyl chloride as dissolved in 10 ml of THF was dropwise added thereto with cooling with ice, and then stirred overnight at room temperature. The reaction mixture was poured into ice water, extracted with ethyl acetate, and washed with a small amount of water. After the resulting product was dried with anhydrous sodium sulfate, the solvent was evaporated out under reduced pressure. The residual product was purified through column chromatography (silica gel; n-hexane:ethyl acetate=4:1) to obtain 3.26 g of the intended compound.
Synthesis Example 10 Synthesis of 2-(2-tert-butyloxazol-4-yl)-3-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)-3-ethoxymethoxyacrylonitrile (Compound No. V-44)
0.6 g of 2-{2-tert-butyloxazol-4-yl}-3-(5-chloro-3-trifluoromethyl-1-methyl-pyrazol-4-yl)-3-hydroxyacrylonitrile was dissolved in 5 ml of THF, and 0.07 g of 60% sodium hydride was added thereto with cooling with ice, and then stirred for 15 minutes at room temperature. 0.17 g of ethoxymethyl chloride was added thereto and stirred for 6 days at room temperature. The reaction mixture was poured into ice water, extracted with ethyl acetate, and washed with saturated saline. The resulting product was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residual product was purified through silica gel thin-layer chromatography (ethyl acetate:n-hexand=1:4) to obtain 0.1 g of the intended compound in vitreous state.
1H-NMR (CDCl3, δ ppm); 1.17 (3H, t), 1.41 (9H, s), 3.98 (3H, s), 5.03 (2H, s), 8.00 (1H, s)
Synthesis Example 11 Synthesis of ethyl 2-phenyl-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-hydroxyacrylate (Compound No. IV-91)
8.2 g (50 mmols) of ethyl phenylacetate and 10.7 g (50 mmols) of 3,5-dichloro-1-methylpyrazole-4-carboxylic acid chloride were dissolved in 100 ml of dry tetrahydrofuran, and 14 g (125 mmols) of potassium tert-butoxide at room temperature. The reaction mixture was stirred at room temperature for 1 hour, and 300 ml of water was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 17 g of the intended ethyl 2-phenyl-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-hydroxyacrylate.
1H-NMR (CDCl3, δ ppm); 1.1-1.5 (3H, m), 3.59 (1.5H, s), 3.73 (1.5H, s), 3.95-4.45 (2H, m), 5.58 (0.5H, s), 7.0-7.35 (5H, m), 13.21 (0.5H, s)
Synthesis Example 12 Synthesis of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenyl-2-bromoethanone (Compound No. IV-90)
1) 17 g (50 mmols) of ethyl 2-phenyl-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-hydroxyacrylate was dissolved in 50 ml of 6 N HCl and 250 ml of 1,4-dioxane, and heated under reflux for 15 hours. The reaction mixture was poured into 500 ml of ice water, and precipitated crystals were taken out through filtration to obtain 8 g of the intended 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenylethanone as white crystals. m.p.: 94-96° C.
2) 5.38 g (20 mmols) of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenylethane was dissolved in 50 ml of chloroform, and stirred at room temperature for 1 hour, and the solvent was distilled off under reduced pressure to obtain the intended 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenyl-2-bromoethanone as white crystals. m.p.: 74.5-75.5° C.
Synthesis Example 13 Synthesis of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-1-pivaloyloxy-2-phenyl-2-bromoethylene (Compound No. IV-92)
0.55 g (1.58 mmols) of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenyl-bromoethane and 0.18 g (1.74 mmols) of triethylamine were dissolved in 4 ml of dry tetrahydrofuran, and 0.19 g (1.58 mmols) of pivalic acid chloride was added thereto at room temperature. After the reaction mixture was stirred for 16 hours at room temperature, 10 ml of water was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified through silica gel column chromatography to obtain 0.23 g of the intended 1-(3,4-dichloro-1-methylpyrazol-4-yl)-1-pivaloyloxy-2-phenyl-2-bromoethylene as a colorless liquid (E-Z mixture).
1H-NMR (CDCl3, δ ppm); 1.05 (9H, s), 3.81 (3H, s), 7.37 (5H, m): major 1.32 (9H, s), 3.62 (3H, s), 7.24 (5H, m): minor
Synthesis Example 14 Synthesis of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-{2-(1-methylcyclohexan-1-yl}-thiazol-4-yl-2-diethylphosphonoethanone (Compound No. II-156)
1) 4.15 g (18.1 mmols) of 2-(1-methyl-cyclohexan-1-yl)-4-chloromethylthiazole and 3.32 g (20 mmols) of trimethyl phosphate were mixed and heated under reflux for 16 hours. The reaction mixture was cooled to room temperature, and purified through silica gel column chromatography to obtain 4.63 g of the intended diethyl {2-(1-methylcyclohexan-1-yl-thiazol-4-yl}methylphosphonate as a colorless liquid.
1H-NMR (CDCl3, δ ppm); 1.25 (3H, t, J=7.2 Hz), 1.31 (3H, s), 1.1-2.3 (1OH, m), 3.33 (2H, d, J=20.4 Hz), 4.04 (4H, dd, J=7.2, 7.2 Hz), 7.01 (1H, m)
2) 0.85 g (4 mmols) of 3,5-dichloro-1-methylpyrazole-4-carboxylic acid chloride and 1.32 g (4 mmols) of diethyl {2-(1-methylcyclohexan-1-yl-thiazol-4-yl}methylphosphonate were dissolved in 15 ml of dry tetrahydrofuran, and 1.12 g (10 mmols) of potassium t-butoxide was added thereto at room temperature. The reaction mixture was stirred for 1 hour at room temperature, and 20 ml of water was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified through silica gel column chromatography to obtain 0.4 g of the intended 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-{2-(1-methylcyclohexan-1-yl)-thiazol-4-yl}-2-diethylphosphonoethanone.
1H-NMR (CDCl3, δ ppm); 1.23 (3H, t, J=7.2 Hz,), 1.23 (3H, s), 1.1-2.3 (1OH, m), 3.79 (3H, s), 4.09 (2H, dd, J=7.2, 7.2 Hz), 5.90 (1H, d, J=22.8 Hz), 7.43 (1H, m)
Synthesis Example 15 Synthesis of allyl 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)-3-hydroxyacrylate (Compound No. I-133)
1) Potassium carbonate (1.53 g) was added to an acetonitrile (10 mL) solution of 3-(2,6-difluorophenyl)-pyrazole (1 g) and allyl 2-bromoacetate (1.49 g), and refluxed for 3 hours. The resulting product was extracted with acetate and diluted hydrochloric acid added thereto at room temperature. The organic layer was dried over anhydrous magnesium sulfate and concentrated, and the resulting concentrate was purified through silica gel column chromatography (chloroform) to obtain allyl 2-{3-(2,6-difluorophenyl) pyrazol-1-yl}acetate (1.5 g).
1H-NMR (CDCl3, δ ppm); 4.70 (2H, d, J=6.0 Hz), 5.10 (2H, s), 5.30-5.60 (2H, m), 5.70-6.40 (1H, m), 6.50-7.80 (5H, m)
2) Potassium butoxide (0.5 g) was added to a THF (10 mL) solution of allyl 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}acetate (0.5 g) and 5-chloro-1-methyl-3-trifluoromethylpyrazole-4-carbonyl chloride (0.44 g) at 0° C. and stirred for 5 minutes. Water (5 ml) was added thereto, and then extracted with diluted hydrochloric acid and ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, and then concentrated, and the resulting concentrate was purified through silica gel column chromatography (chloroform) to obtain the intended product, Compound No. I-133 (0.89 g).
1H-NMR (CDCl3, δ ppm): 3.95 (3H, s), 4.80 (2H, d, J=6.0 Hz), 5.20-5.60 (2H, m), 5.60-6.40 (1H, m), 6.45-7.90 (6H, m)
Synthesis Example 16 Synthesis of 2-bromo-2-{3-(2,6-difluorophenyl) pyrazol-1-yl}-1-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)-1-hydroxyethylene (Compound No. I-134)
1) Formic acid (60 mg) was added to a THF (1 mL) solution of palladium acetate (7 mg) and triphenylphosphine (17 mg) and stirred for 5 minutes at room temperature in a nitrogen atmosphere. A THF (5 mL) solution of Compound I-133 (0.32 g) was added thereto and refluxed for 1 hour. The reaction mixture was left to be at room temperature, and concentrated, and the resulting concentrate was purified through silica gel column chromatography (chloroform) and recrystallization (chloroform-diisopropyl ether) to obtain 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)ethan-1-one (0.1 g). m.p.: 152-154° C.
2) A THF solution (0.27 mL) of 1M lithium hexamethyldisilazide was added to a THF solution of 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)ethan-1-one (0.1 g) at −78° C. and stirred at the same temperature in a nitrogen atmosphere. To the resulting solution was added a THF (2 mL) solution of carbon tetrabromide (0.098 g), and then gradually heated up to room temperature. Water (1 mL) was added thereto, and then extracted with diluted hydrochloric acid and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized from chloroform-diethyl ether) to obtain the intended product, Compound No. I-134 (0.062 g). m.p.: 123-125° C.
Synthesis Example 17 Synthesis of 2-bromo-2-{3-(2,6-difluorophenyl) pyrazol-1-yl}-1-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)-1-pivaloyloxyethylene (Compound No. I-135)
Triethylamine (0.3 g) and pivalic acid chloride (0.23 g) were added in that order to a chloroform (25 ml) solution of Compound No. I-134 (0.47 g) at 0° C., and stirred at room temperature for 1 hour. The resulting product was extracted with water and chloroform. The organic layer was dried with anhydrous magnesium sulfate, concentrated, and purified through silica gel column chromatography (chloroform) to obtain the intended product, Compound No. I-135 (0.4 g).
1H-NMR (CDCl3, δ ppm); 1.25 (9H, s), 3.90 (3H, s), 6.55-7.80 (5H, m)
In accordance with the above-mentioned reaction schemes or Examples, various compounds of the present invention were produced, of which the structure and the melting point are shown in Table 15 to Table 19 below. Unless otherwise specifically indicated, the compounds shown in these are in the form of a mixture of E-form and Z-form. The abbreviations in these have the same meanings as those mentioned above.
TABLE 15
Figure USRE038188-20030715-C00380
m.p.
No. R1 R2 R3 E B A (° C.)
I-1 Ph H H CN H A1 144-145
I-2 Ph Cl H CN H A1 300<
I-3 Ph H Me CN H A1 300<
I-4 Ph Me H CN H A1 141-143
I-5 Ph H H CN B1 A1 75-77*
I-6 Ph H H CN B2 A1 viscous oil
I-7 Ph CO2Et H CN H A1 202-203
I-8 Ph H H CN H A2 300<
I-9 Ph H H CN H A7 124-125
I-10 Ph H H CN H A8 265-267
I-11 2-pyridyl H H CN H A1 290<
I-12 2-pyridyl H H CN H A2 300<
I-13 2-pyridyl H H CN H A3 260-267
I-14 2-pyridyl H H CN H A4 300<
I-15 2-pyridyl H H CN H A6 297-298
I-16 2-pyridyl H H CN H A7 163-165
I-17 2-pyridyl H H CN H A8 300<
I-18 2-pyridyl H H CN H A9 240-245
I-19 2-pyridyl H H CN H A10 261-266
I-20 2-pyridyl H H CN H A11 232-234
I-21 2-pyridyl H H CN H A12 284-287
I-22 2-pyridyl H H CN H A13 300<
I-23 2-pyridyl H H CN B7 A7 103-110*
I-24 2-pyridyl H H CN B8 A1 viscous oil
I-25 3-pyridyl H H CN H A1 298-300
I-26 3-pyridyl H H CN H A2 158-160
I-27 3-pyridyl H H CN H A7 168-169
I-28 4-pyridyl H H CN H A1 251-253
I-29 2-F—Ph H H CN H A1 125-126
I-30 2-F—Ph H H CN H A2 281-282
I-31 2-F—Ph Cl H CN H A1 281-287
I-32 3-F—Ph H H CN H A2 300<
I-33 4-F—Ph H H CN H A2 169-173
I-34 2-Cl—Ph H H CN H A1 viscous oil
I-35 2-Cl—Ph H H CN H A2 viscous oil
I-36 3-Cl—Ph H H CN H A1 141-149
I-37 3-Cl—Ph H H CN H A7 291-293
I-38 4-Cl—Ph H H CN H A1 186-188
I-39 4-Cl—Ph H H CN H A7 300<
I-40 2,6-F2—Ph H H CN H A1 267-269
I-41 2,6-F2—Ph H H CN H A2 300<
I-42 2,6-F2—Ph H H CN H A7 242-243
I-43 2,6-Cl2—Ph H H CN H A1 147-148
I-44 2,6-Cl2—Ph H H CN H A2 100-102
I-45 tBu H H CN H A1 viscous oil
I-46 tBu H H CN H A2 65-67
I-47 2-MeO—Ph H H CN H A1 300<
I-48 2-MeO—Ph H H CN H A2 300<
I-49 H CO2Et Ph CN H A1 236-237
I-50 Me Ph H CN H A1 viscous oil
I-51 cHex H H CN H A1 204-205
I-52 1-naphthyl H H CN H A1 225-227
I-53 2-thienyl H H CN H A1 146-147
I-54 2-thienyl H H CN H A7 271-273
I-55 Ph H H CN H A34 173.3-174.1
I-56 Ph H H CN B1 A34 viscous oil*
I-57 Ph H H CN B7 A1 140-141*
I-58 Ph H H CN B8 A1 50-51*
I-59 Ph H H CN CO2 tBu A1 viscous oil
I-60 tBu CO2Me H CN H A1 105-106
I-61 tBu CO2Me H CN B7 A1 125-126
I-62 Ph H H CN B7 A2 viscous oil
I-63 2,6-F2—Ph H H CN B8 A2 200-201
I-64 Ph H H CN B6 A2 viscous oil
I-65 2,6-F2—Ph H H CN Na 2,6-(MeO)2—Ph 300<
I-66 2,6-F2—Ph H H CN Na 2-CF3O—Ph 282.8-287.2
I-67 2,6-F2—Ph H H CN Na 2-MeO—Ph 300<
I-68 2,6-F2—Ph H H CN H 2-CF3O—Ph 157.9-160.1
I-69 2-pyridyl H H CN B8 A7 118-119*
I-70 2,6-F2—Ph H H CN B7 A2 viscous oil
I-71 Ph H H CN H 2-Cl—Ph 108-109
I-72 Ph H H CN H 2,6-F2—Ph 167-168
I-73 Ph H H CN H 2,6-Cl2—Ph 170-171
I-74 Ph H H CN H 2-CF3—Ph viscous oil
I-75 Ph H H CN H 1-naphthyl 137-138
I-76 Ph Ph H CN H A2 145-147
I-77 Ph H H CN H 2-Cl-4-F—Ph 94-95
I-78 Ph H H CN B35 A2 164-165
I-79 2,6-F2—Ph H H CN H 2-Me—Ph 113.1-119.8
I-80 2,6-F2—Ph H H CN H 2-Cl-6-F—Ph 144-146
I-81 2,6-F2—Ph H H CN H 2-NO2—Ph 176-179
I-82 2,6-F2—Ph H H CN H 2-AcO—Ph vitreous state
I-83 2,6-F2—Ph H H CN H 2,6-Me—Ph vitreous state
I-84 2-pyridyl H H CN H 2,6-F2—Ph 188-189
I-85 2-pyridyl H H CN H 2,6-Cl2—Ph 278-280
I-86 2-pyridyl H H CN H 2-NO2—Ph 285-287
I-87 2-pyridyl H H CN H 2-MeO—Ph 275-276
I-88 2-pyridyl H H CN H 2-CO2Me—Ph 248-249
I-89 2-pyridyl H H CN B7 2-Cl—Ph 124-125
I-90 2-pyridyl H H CN Na 2-Cl—Ph 278-280
I-91 2-pyridyl H H CN H pyridin-2-yl 216-217
I-92 2-pyridyl H H CN COnC17H35 A7 58-59
I-93 t-Bu CO2Me H CN H 2-Cl-4-F—Ph 114-115
I-94 t-Bu CO2Me H CN B7 A2 105-106
I-95 t-Bu CO2Me H CN H A2 102-103
I-96 t-Bu H H CN B7 A2 viscous oil
I-97 t-Bu H H CN B7 A2 viscous oil#1
I-98 t-Bu NO2 H CN B7 A2 viscous oil
I-99 t-Bu Br H CN B7 A2 viscous oil
I-100 t-Bu CN H CN H A2 178-180
I-101 t-Bu CN H CN CO2 iBu A2 vitreous state
I-102 t-Bu CN H CN CO2 tBu A2 201-202.5#2
I-103 t-Bu CN H CN CO2Ph A2 vitreous state
I-104 t-Bu Cl H CN B7 A2 viscous oil
I-105 t-Bu CO2Me H CN CO2 iBu A2 155.8-156.9
I-106 t-Bu Cl H CN H A2 viscous oil
I-107 t-Bu NO2 H CN H A2 87-88
I-108 t-Bu CO2 nHex H CN H A2 vitreous state
I-109 t-Bu CO2Me H CN B8 A2 152.1-153.5
I-110 t-Bu Me H CN H A2 vitreous state
I-111 t-Bu CO2Me H CN COnC17H35 A14 viscous oil
I-112 t-Bu CO2Me H CN B7 A14 viscous oil
I-113 t-Bu CO2Me H CN H A14 101-102
I-114 t-Bu Me H CN B7 A2 vitreous state
I-115 t-Bu CO2Me H CN B7 A3 131-132
I-116 t-Bu CO2Me H CN Me A2 166-167*
I-117 t-Bu CO2Me H CN B3 A14 viscous oil
I-118 t-Bu CO2Me H CN H A21 152.6-154
I-119 t-Bu CO2Me H CN COnC9H19 A3 viscous oil
I-120 t-Bu CO2Me H CN B7 A15 125-127*
I-121 t-Bu CO2Me H CN H A15 138-139
I-122 t-Bu CO2Me H CN B7 A21 viscous oil
I-123 t-Bu CO2Me H CN COnC5H11 A21 viscous oil
I-124 t-Bu CO2Me H CN COnC5H11 A21 viscous oil#3
I-125 H H 2,6-F2—Ph CN H A2 157.4-162.4
I-126 H Ph H CN H A1 vitreous state
I-127 H t-Bu H CN B7 A2 vitreous state
I-128 H t-Bu H CN H A2 vitreous state
I-129 Ph H H CO2Me H A1 158-160
I-130 Ph H H CO2Me B7 A2 viscous oil
I-131 2,6-F2—Ph H H CO2Me H A2 248-250
I-132 2,6-F2—Ph H H COMe H A2 vitreous state
I-133 2,6-F2—Ph H H CO2CH2CH═CH2 H A2 vitreous state
I-134 2,6-F2—Ph H H Br H A2 123-125
I-135 2,6-F2—Ph H H Br B7 A2 vitreous state
I-136 2-pyridyl H H CN B7 A37 86-94#4
I-137 2-pyridyl H H CN B7 A10 92-93
I-138 2-pyridyl Cl H CN B7 A7 viscous oil*
*E-form or Z-form
#1geometric isomer of I-96
#2geometric isomer of I-101
#3geometric isomer of I-123
#4mixture of E/Z = 2/1
TABLE 16
Figure USRE038188-20030715-C00381
m.p.
No. R E B A (° C.)
II-1 Ph CN H A1 200-205
II-2 2-Cl—Ph CN H A2 137-138
II-3 t-Bu CN H A2 151-153
II-4 t-Bu CN B3 A2 147-150*
II-5 t-Bu CN B7 A2 89.5-92*
II-6 t-Bu CN H A1 viscous oil*
II-7 t-Bu CN B7 A1 viscous oil*
II-8 t-Bu CN H 2,6-F2—Ph 90-92.5
II-9 t-Bu CN H 2-Cl—Ph 96.2-98.6
II-10 t-Bu CN B6 A2 vitreous state*
II-11 t-Bu CN B5 A2 viscous oil
II-12 t-Bu CN B8 A2 viscous oil
II-13 t-Bu CN SO2(4-Cl—Ph) A2 vitreous state*
II-14 t-Bu CN H 2,6-Cl2—Ph 150.3-151.7
II-15 t-Bu CN H 2-CF3—Ph 71.9-79.6
II-16 t-Bu CN H A3 viscous oil
II-17 t-Bu CN B7 A3 viscous oil*
II-18 t-Bu CN CO2Et A2 viscous oil
II-19 t-Bu CN CO2CH2Ph A2 viscous oil
II-20 t-Bu CN CONMe2 A2 136.7-138.2
II-21 t-Bu CN CH2CO2Me A2 viscous oil
II-22 t-Bu CN PO(OEt)2 A2 viscous oil
II-23 2-pyridyl CN H A2 184.5-188.5
II-24 2-pyridyl CN H A7 210.3-218.8
II-25 2-pyridyl CN B7 A7 162.7-167*
II-26 2-pyridyl CN B7 A2 vitreous state*
II-27 2-pyridyl CN H A3 148-151
II-28 2-pyridyl CN B7 A3 vitreous state*
II-29 2-pyridyl CN H A35 188-193
II-30 2-pyridyl CN B7 A35 200.5-202.5*
II-31 2-pyridyl CN H A36 viscous oil
II-32 2-pyridyl CN B7 A36 viscous oil
II-33 c-Hex CN H A2 126.5-128.1
II-34 c-Hex CN H 2,6-F2—Ph 110.9-112.7
II-35 c-Hex CN B7 2,6-F2—Ph 111.2-117.4*
II-36 c-Hex CN B7 A2 viscous oil*
II-37 2,6-F2—Ph CN H A2 176.8-178.2
II-38 2,6-F2—Ph CN B7 A2 95.9-98.0*
II-39 2-Cl—Ph CN H A2 172.9-175.2
II-40 t-Bu CN B35 A2 vitreous state
II-41 t-Bu CN B35 A2 vitreous state#4
II-42 t-Bu CN B36 A2 vitreous state
II-43 t-Bu CN H A13 168-173
II-44 t-Bu CN B28 A2 vitreous state
II-45 t-Bu CN B30 A2 vitreous state
II-46 t-Bu CN B30 A2 vitreous state#5
II-47 t-Bu CN CO(2-Me—Ph) A2 vitreous state
II-48 t-Bu CN B38 A2 vitreous state
II-49 t-Bu CN B37 A2 vitreous state
II-50 t-Bu CN nicotinoyl A2 vitreous state
II-51 t-Bu CN B40 A2 vitreous state
II-52 t-Bu CN CO2 iBu A2 viscous oil
II-53 t-Bu CN CO2Ph A2 viscous oil
II-54 t-Bu CN B41 A2 viscous oil
II-55 t-Bu CN CO2 nHex A2 viscous oil
II-56 t-Bu CN H 3-Cl—Ph 89.7-91.1
II-57 t-Bu CN H 3-F—Ph 63.7-64.4
II-58 t-Bu CN H 2-Br—Ph 86-87
II-59 t-Bu CN H 2-I—Ph vitreous state
II-60 t-Bu CN H 2-Cl-6-F—Ph 109.6-110.6
II-61 t-Bu CN CO(2-MeS—Ph) A2 vitreous state
II-62 t-Bu CN H 2-MeS—Ph 120.6-122.1
II-63 t-Bu CN H A22 113-118
II-64 t-Bu CN B7 A22 98-99.5*
II-65 t-Bu CN B15 A22 viscous oil
II-66 t-Bu CN B38 A13 viscous oil
II-67 t-Bu CN B39 A2 vitreous state
II-68 t-Bu CN CO(4-Cl—Ph) A2 vitreous state
II-69 t-Bu CN CO(3-Cl—Ph) A2 vitreous state
II-70 t-Bu CN B7 2,6-F2—Ph viscous oil
II-71 t-Bu CN B8 2,6-F2—Ph viscous oil
II-72 t-Bu CN B6 2,6-F2—Ph 150.2-151.3
II-73 t-Bu CN CO2 nPr A2 viscous oil
II-74 t-Bu CN CO2 nBu A2 viscous oil
II-75 t-Bu CN B6 A13 viscous oil
II-76 t-Bu CN CO2CH2CCl3 A2 viscous oil
II-77 t-Bu CN CO(2-Cl—Ph) A2 vitreous state
II-78 t-Bu CN CO(3-CF3—Ph) A2 vitreous state
II-79 t-Bu CN CO(4-CF3—Ph) A2 vitreous state
II-80 t-Bu CN CO(3-NO2—Ph) A2 vitreous state
II-81 t-Bu CN CO(2-Cl-6-F—Ph) A2 vitreous state
II-82 t-Bu CN CO2 cPen 2,6-F2—Ph vitreous state
II-83 t-Bu CN 3-Cl-pivaloyl A2 viscous oil*
II-84 t-Bu CN CO2 iPr A2 viscous oil
II-85 t-Bu CN CO2CH2CH2Cl A2 viscous oil
II-86 t-Bu CN CO2CHClCH3 A2 viscous oil
II-87 t-Bu CN COiPr A2 viscous oil
II-88 t-Bu CN isonicotinoyl A2 viscous oil
II-89 t-Bu CN picolinoyl A2 viscous oil
II-90 t-Bu CN CO(4-Me—Ph) A2 viscous oil
II-91 t-Bu CN CO(4-NO2—Ph) A2 viscous oil
II-92 t-Bu CN methacryloyl A2 viscous oil
II-93 t-Bu CN B15 A2 vitreous state
II-94 t-Bu CN PhCH2 A2 viscous oil
II-95 t-Bu CN Me A2 136.5-138
II-96 t-Bu CN CBrF2 A2 84-86.5
II-97 t-Bu CN COnPr A2 viscous oil
II-98 t-Bu CN COiBu A2 viscous oil
II-99 t-Bu CN B43 A2 vitreous state
II-100 t-Bu CN PhCOCH2 A2 148-152*
II-101 t-Bu CN B42 A2 128-129.5*
II-102 t-Bu CN H A14 98-99
II-103 t-Bu CN H A16 viscous oil
II-104 t-Bu CN B7 A16 viscous oil*
II-105 t-Bu CN cinnamoyl A2 vitreous state
II-106 t-Bu CN H A23 109-112
II-107 t-Bu CN B7 A23 120-122.5
II-108 t-Bu CN B7 A14 viscous oil
II-109 t-Bu CN B7 A14 viscous oil#6
II-110 t-Bu CN COnC17H35 A14 viscous oil
II-111 t-Bu CN PhCH2CO A2 viscous oil
II-112 t-Bu CN B7 A17 viscous oil
II-113 t-Bu CN H A17 140-143
II-114 t-Bu CN H A24 115-117
II-115 t-Bu CN CO2 iBu A24 vitreous state
II-116 t-Bu CN B7 A2 69.5-73.5#7
II-117 t-Bu CN H A25 107-109
II-118 t-Bu CN B7 A25 viscous oil
II-119 t-Bu CN H A31 116-117
II-120 t-Bu CN CO2(4-Me—Ph) A31 92-93
II-121 t-Bu CN H A26 133.2-135.4
II-122 t-Bu CN B7 A26 133.9-145
II-123 t-Bu CN H A27 46-47
II-124 t-Bu CN H A28 168-169
II-125 t-Bu CN H A29 94.7-95.4
II-126 t-Bu CN B8 A29 viscous oil
II-127 t-Bu CN B8 A29 viscous oil#8
II-128 t-Bu CN H A32 133.9-134.4
II-129 t-Bu CN H A33 220-230
II-130 2,6-F2—Ph CN H 2-6-F2—Ph 138-143
II-131 2-pyridyl CN B7 A18 115-145
II-132 2-pyridyl CN H A18 176-178
II-133 2-pyridyl CN H A9 191.5-195
II-134 2-pyridyl CN B7 A9 101-103
II-135 2-pyridyl CN H A8 211-216
II-136 2-pyridyl CN H A10 189-193
II-137 2-pyridyl CN CO2(4-F—Ph) A10 137-142
II-138 2-pyridyl CN H A24 188-191.5
II-139 2-pyridyl CN B7 A24 160-163.5
II-140 2-pyridyl CN B7 A30 123-125
II-141 2-pyridyl CN H A30 165-166
II-142 2-pyridyl CN H A13 149.5-151
II-143 NMePh CN H A7 161.5-164
II-144 NMePh CN B7 A7 120-123
II-145 NMePh CN H A2 vitreous state
II-146 NMePh CN B7 A2 vitreous state
II-147 1-piperidyl CN B3 A2 165.5-169
II-148 1-piperidyl CN H A2 151-153
II-149 1-piperidyl CN H A7 187-190
II-150 1-piperidyl CN B8 A7 viscous oil
II-151 1-piperidyl CN B8 A2 120-121.5
II-152 1-piperidyl CN B6 A2 viscous oil
II-153 1-naphthyl CN H A2 161-163
II-154 1-naphthyl CN B7 A2 vitreous state
II-155 t-Bu CO2Me H A2 viscous oil
II-156 1-Me-1-cHex PO(OEt)2 H A1 vitreous state
II-157 t-Bu CO2Et H A1 viscous oil
II-158 t-Bu CO2Et B7 A1 viscous oil
II-159 1-Me-1-cHex CN H A2 vitreous state
II-160 n-Pen CN H A2 73-75
II-161 t-Bu CN B8 A32 108-112
II-162 t-Bu CN H A1 viscous oil
II-163 t-Bu CO2Me H A1 89-92
II-164 t-Bu SO2Ph H A1 145-148
II-165 t-Bu SO2Ph B7 A1 122-123
II-166 t-Bu SO2Ph B7 A1 152-153#14
II-167 t-Bu CO2Me B7 A1 viscous oil
II-168 t-Bu CO2Me B7 A2 76-78
II-169 t-Bu CO2CH2CH═CH2 H A2 viscous oil
II-170 t-Bu CO2CH2CH═CH2 B7 A2 viscous oil
II-171 1-Me-1-cHex CN B7 A2 vitreous state
II-172 n-Pen CN B7 A2 vitreous state
II-173 1-Me-1-cHex CN CH2O(CH2)2OCH3 A2 97-98*
II-174 t-Bu 5-Me-1,3,4- H A1 vitreous state
oxadiazol-2-yl
II-175 t-Bu 5-Me-1,3,4- H A1 vitreous state
oxadiazol-2-yl
II-176 t-Bu Bu H A2 viscous oil
II-177 t-Bu CN B6 A13 104-107*
II-178 t-Bu 5-Me-1,3,4- B7 A1 134-137
oxadiazol-2-yl
II-179 t-Bu 5-Me-1,3,4- B7 A1 114-116#15
oxadiazol-2-yl
II-180 t-Bu 5-Me-1,3,4- B7 A1 86-90*
thiadiazol-2-yl
*E-form or Z-form
#4geometric isomer of II-40
#5geometric isomer of II-45
#6geometric isomer of II-108
#7geometric isomer of II-5
#8geometric isomer of II-126
#14geometric isomer of II-165
#15geometric isomer of II-178
TABLE 17
Figure USRE038188-20030715-C00382
m.p.
No. R E B A (° C.)
III-1 Ph CN B4 A1 viscous oil*
III-2 Ph CN B5 A1 40-41*
III-3 t-Bu CN B1 A1 151-152*
III-4 t-Bu CN B4 A1 77-79*
III-5 t-Bu CN B6 A2 55-61*
III-6 t-Bu CN B7 A2 viscous oil*
III-7 2-pentyl CN B1 A1 viscous oil
III-8 4-tBu—Ph CN B1 A5 viscous oil
III-9 t-Bu CN Na A2 165-174
III-10 t-Bu CN B9 A2 viscous oil
III-11 t-Bu CN B10 A2 185-186*
III-12 t-Bu CN B11 A2 viscous oil
III-13 2-NO2—Ph CN B9 A1 168-171*
III-14 1-naphthyl CN B9 A7 136-138*
III-15 t-Bu CN B7 A2 viscous oil#9
III-16 Ph CN B4 A1 solid#10
III-17 t-Bu CN B4 A1 viscous oil#11
III-18 2-Cl-6-F—Ph CN B7 A2 152-153
III-19 2,6-F2—Ph CN B7 A2 vitreous state*
III-20 Ph CN B5 A1 105-107#12
III-21 Ph CN B7 A2 viscous oil
*E-form or Z-form,
#9geometric isomer of III-6,
#10geometric isomer of III-1,
#11geometric isomer of III-4,
#12geometric isomer of III-2
TABLE 18
Figure USRE038188-20030715-C00383
m.p.
No. G E B A (° C.)
IV-1 2-CF3 CN H A1 viscous oil
IV-2 3-CF3 CN H A1 159-163
IV-3 3-CF3 CN B1 A1 174-175
IV-4 4-CF3 CN H A1 176-179
IV-5 4-CF3 CN B1 A1 viscous oil
IV-6 2-CF3 CN CSNMe2 A1 viscous oil
IV-7 3(1-CN-1-Me)—Et CN H A1 viscous oil
IV-8 3(1-CN-1-Me)—Et CN B1 A1 148-155
IV-9 3-OPh CN H A1 103-110
IV-10 3-OPh CN B7 A1 viscous oil
IV-11 4-OPh CN H A1 148-150
IV-12 4-OPh CN B7 A1 viscous oil
IV-13 4-Et CN H A1 148-149
IV-14 4-Et CN B7 A1 81-82
IV-15 4-Et CN B5 A1 viscous oil
IV-16 4-i-Pr CN H A1 126-127
IV-17 4-i-Pr CN B7 A1 105-106
IV-18 4-t-Bu CN H A1 117-118
IV-19 4-t-Bu CN B1 A1 viscous oil
IV-20 4-OCF3 CN H A1 128-129
IV-21 4-OCF3 CN B7 A1 96-99
IV-22 3,4-methylene- CN H A1 129-131
dioxy
IV-23 3,4-methylene- CN B7 A1 viscous oil
dioxy
IV-24 4-t-Bu CN B7 A2 viscous oil
IV-25 4-t-Bu CN B15 A2 viscous oil
IV-26 4-t-Bu CN H A2 139-140
IV-27 4-t-Bu CN B7 A13 87-88
IV-28 4-t-Bu CN H A13 141-142
IV-29 4-t-Bu CN B8 A2 vitreous state
IV-30 4-t-Bu CN H A19 169.5-173
IV-31 4-t-Bu CN H A20 vitreous state
IV-32 4-t-Bu CN B7 A20 146-148
IV-33 4-t-Bu CN B15 A14 viscous oil
IV-34 4-t-Bu CN B7 A19 vitreous state
IV-35 4-t-Bu CN B7 A1 viscous oil*
IV-36 4-t-Bu CN B8 A1 viscous oil
IV-37 4-t-Bu CN H A24 vitreous state
IV-38 4-t-Bu CN B8 A24 vitreous state
IV-39 4-t-Bu CN CO2Et A1 viscous oil
IV-40 4-t-Bu CN CO2 tBu A1 viscous oil
IV-41 4-t-Bu CN COCO2CH3 A1 viscous oil
IV-42 4-s-Bu CN H A2 107-108
IV-43 4-s-Bu CN B15 A2 77-85
IV-44 4-i-Pr CN B15 A1 100-101
IV-45 4-i-Pr CN B15 A2 viscous oil
IV-46 4-i-Pr CN H A2 98-99
IV-47 4-i-Pr CN B8 A2 viscous oil
IV-48 4-i-Pr CN CO(4-NO2—Ph) A2 vitreous state
IV-49 4-Et CN B15 A1 viscous oil
IV-50 4-Ph CN H A1 vitreous state
IV-51 4-Ph CN H A2 vitreous state
IV-52 4-Ph CN H A12 vitreous state
IV-53 4-Ph CN H A13 167-169
IV-54 3,4-Cl2 CN H A1 vitreous state
IV-55 4-Cl CN H A1 vitreous state
IV-56 2-F-4-CF3 CN H A2 vitreous state
IV-57 2-F-4-CF3 CN B7 A2 vitreous state
IV-58 2-F-4-CF3 CN B15 A2 vitreous state
IV-59 4-NO2 CN H A1 186-188
IV-60 4-MeO CN H A1 108-110
IV-61 4-MeO CN B15 A1 viscous oil*
IV-62 4-i-PrO CN H A1 127-131
IV-63 4-i-PrO CN H A2 141.4-148.3
IV-64 4-i-PrO CN B15 A1 viscous oil
IV-65 4-i-PrO CN B15 A2 viscous oil
IV-66 4-i-PrO CN B6 A2 viscous oil
IV-67 4-n-BuO CN H A1 101-104
IV-68 4-n-BuO CN B15 A1 75-70
IV-69 4-n-BuO CN H A2 104.6-105.4
IV-70 4-n-BuO CN B8 A1 77.1-80.7
IV-71 4-n-BuO CN B15 A2 viscous oil
IV-72 4-t-amyl CN B15 A2 viscous oil
IV-73 4-allyloxy CN H A1 vitreous state
IV-74 4-allyloxy CN B15 A1 vitreous state
IV-75 4-(Cl2C═CHCH2O) CN H A1 vitreous state
IV-76 4-(Cl2C═CHCH2O) CN B15 A1 vitreous state
IV-77 4-(ClCCCH2O) CN H A1 vitreous state
IV-78 4-PhCH2O CN H A1 152.9-154.7
IV-79 4-PhCH2O CN H A2 189-190.5
IV-80 4-PhCH2O CN B15 A2 123-129
IV-81 4-MeOCH2O CN H A1 130.4-131.7
IV-82 4-CF3CH2O CN H A1 100-103
IV-83 4-pivaloyl CN B15 A2 vitreous state
IV-84 4-pivaloyl CN H A2 vitreous state
IV-85 4-Me2NCO2 CN H A2 vitreous state
IV-86 4-Me2NCO2 CN B15 A2 vitreous state
IV-87 4-Me2NCO2 CN B7 A2 vitreous state
IV-88 4-t-Bu PO(OEt)2 H A1 87-88
IV-89 4-t-Bu PO(OEt)2 B1 A1 121-124
IV-90 H Br H A1 74.5-75.5
IV-91 H CO2Et H A1 viscous oil
IV-92 H Br B7 A1 viscous oil
IV-93 4-t-Bu PO(OEt)2 H A2 viscous oil
IV-94 4-t-Bu CN COCO2Et A1 viscous oil
IV-95 4-t-Bu CN CO2 iBu A2 viscous oil
IV-96 4-t-Bu CN CO2 iBu A13 104-105
IV-97 4-t-Bu SO2Ph H A1 143-145
IV-98 H CO2Et B7 A1 viscous oil
IV-99 4-t-Bu CN B3 A1 viscous oil
IV-100 4-t-Bu CN B19 A1 vitreous state
IV-101 4-t-Bu CN CO(4-CO2Me—Ph) A2 vitreous state
IV-102 4-t-Bu CN CO(4-CO2Me—Ph) A13 vitreous state
IV-103 4-t-Bu CO2Me H A2 88-89
IV-104 4-t-Bu CO2Me H A1 123-124
IV-105 4-t-Bu CO2Me B7 A1 77-78
IV-106 4-t-Bu CO2Me B7 A2 viscous oil
IV-107 4-t-Bu SO2Ph B7 A1 98-99
IV-108 4-t-Bu SO2Ph B7 A1 130-131#13
IV-109 4-t-Bu CN B3 A2 71-72*
IV-110 4-CHF2O CN H A2 vitreous state
IV-111 4-CHF2O CN B15 A2 vitreous state
IV-112 4-CHF2O CN B7 A2 vitreous state
IV-113 4-CH3CONH CN H A2 247.9-251.9
IV-114 4-CH3CONH CN B7 A2 82.1-84.3
IV-115 4-CO2Me CN H A2 151-152
IV-116 4-CO2Me CN B7 A2 viscous oil*
IV-117 4-vinyl CN H A2 vitreous state
IV-118 4-t-Bu CN B15 A1 78-82
IV-119 4-t-Bu CN methacryloyl A1 viscous oil*
IV-120 4-t-Bu CN COCH═(CH3)2 A1 viscous oil
IV-121 4-t-Bu CN B33 A1 viscous oil
IV-122 4-t-Bu CN CH2OCH2Ph A1 viscous oil
IV-123 4-t-Bu CN B24 A1 viscous oil
IV-124 H Cl H A1 48-49
IV-125 4-t-Bu 5-Me-1,3,4- H A1 149-151
oxadiazol-
2-yl
IV-126 4-SMe CN H A2 154-156
IV-127 4-SMe CN B7 A2 viscous oil*
IV-128 4-SOMe CN H A2 vitreous state
IV-129 4-t-Bu CN B33 A2 viscous oil
IV-130 4-t-Bu CN B3 A13 111-112*
IV-131 4-t-Bu CN B7 A3 viscous oil
IV-132 4-t-Bu CN B3 A3 viscous oil
IV-133 4-t-Bu CN COCH2(4-OMe—Ph) A1 117-123
IV-134 4-SO2Me CN B7 A2 vitreous state*
IV-135 4-SOMe CN B7 A2 vitreous state*
IV-136 4-OCH2Ph-3-Cl CN H A2 vitreous state
IV-137 4-OPri-3-Cl CN H A2 vitreous state
IV-138 4-OBui-3-Cl CN H A2 vitreous state
IV-139 4-t-Bu CN B8 A3 viscous oil
IV-140 4-t-Bu CN B7 2-Cl-4-CF3- 90-91
thiazol-5-yl
*E-form or Z-form
#13geometric isomer of IV-107
TABLE 19
Figure USRE038188-20030715-C00384
No. Q R E B A m.p. (° C.)
V-1 Q9 1-Ph CN H A1 148.7-151.3
V-2 Q9 1-Ph CN H A2 156-157
V-3 Q9 5-Me-1-iPr CN H A2 78-80
V-4 Q9 5-Me-1-iBu CN B7 A2 84-89*
V-5 Q9 5-Me-1-sBu CN B7 A2 99-105
V-6 Q9 5-Me-1-iBu CN H A2 113-114
V-7 Q9 5-Me-1-sBu CN H A2 75-80
V-8 Q9 1-t-Bu CN B7 A2 vitreous state*
V-9 Q9 1-t-Bu CN H 2,6-F2—Ph 111-113
V-10 Q9 1-t-Bu CN H A2 127-129
V-11 Q9 1-pyridin- CN H A2 156.4-158.1
2-yl
V-12 Q9 1-pyridin- CN B15 A2 vitreous state*
2-yl
V-13 Q9 1-pyridin- CN B7 A2 vitreous state*
2-yl
V-14 Q10 1-Ph CN B7 A2 130-131
V-15 Q10 1-Ph CN H A2 207-208
V-16 Q10 1-t-Bu CN B7 A2 viscous oil
V-17 Q10 1-t-Bu CN H A2 viscous oil
V-18 Q11 1-Me-3-tBu CN H A2 vitreous state
V-19 Q11 1-Me-3-tBu CN B7 A2 119-124
V-20 Q12 Ph CN H A2 247-253
V-21 Q12 Ph CN B7 A2 147.5-148.5*
V-22 Q12 Ph CN SO2(4-tBu—Ph) A2 174-176.5
V-23 2-naphthyl — CN B1 A1 viscous oil
V-24 2-naphthyl — CN H A1 140.1-141.1
V-25 2-naphthyl — CN B7 A1 viscous oil
V-26 Q13 — CN H A2 121-122
V-27 Q1 5-Cl CN H A2 160 (decompo-
sition)
V-28 Q1 5-Cl CN B7 A2 79.5-81
V-29 Q2 4-Ph CN H A1 231-232
V-30 Q2 4-t-Bu CN H A1 218-219
V-31 Q3 3-Ph CN H A1 243-245
V-32 Q4 Ph CN H A1 255.8-256.8
V-33 Q4 Ph CN B1 A1 187-190
V-34 Q5 t-Bu CN H A2 158-160
V-35 Q6 t-Bu CN H A2 215-216
V-36 Q7 5-CF3 CN H A1 184-185
V-37 Q7 5-CF3 CN H A2 211-212
V-38 Q7 5-PhCH2O CN H A1 220-221
V-39 Q8 4,6-(MeO)2 CN H A1 149-155
V-40 Q14 t-Bu CN H A1 137.9-143.7
V-41 Q14 t-Bu CN B7 A1 vitreous state
V-42 Q14 t-Bu CN H A2 127.5-128.9
V-43 Q14 t-Bu CN B7 A2 vitreous state
V-44 Q14 t-Bu CN B33 A2 vitreous state
V-45 Q14 t-Bu CN H 2,6-F2—Ph 105.6-108.1
V-46 Q14 t-Bu CN B7 2,6-F2—Ph viscous oil
V-47 Q14 Ph CN H A2 113.0-114.9
V-48 Q14 Ph CN B7 A2 vitreous state
V-49 Q14 Ph CN B15 A2 vitreous state
V-50 Q14 2-Cl—Ph CN H A1 125.5-127.5
V-51 Q14 2-Cl—Ph CN B7 A1 104.0-107.5
V-52 Q14 2-Cl—Ph CN H A2 142.4-143.6
V-53 Q14 2-Cl—Ph CN B15 A2 vitreous state
V-54 Q14 2-Cl—Ph CN B7 A2 vitreous state
V-55 Q14 2,6-F2—Ph CN H A2 136.3-164.7
V-56 Q14 2,6-F2—Ph CN B15 A2 vitreous state
V-57 Q14 2,6-F2—Ph CN B7 A2 vitreous state
V-58 Q14 PhCH2 CN H A2 113.2-114.3
V-59 Q14 PhCH2 CN B15 A2 vitreous state
V-60 Q14 PhCH2 CN B7 A2 vitreous state
V-61 Q14 2-Cl—Ph CN H 2-MeO—Ph 131.4-132.8
V-62 Q14 2-Cl—Ph CN CO2-2-Oct 2-MeO—Ph viscous oil
V-63 Q14 2-Cl—Ph CN B44 2-MeO—Ph vitreous state
V-64 Q14 2-Cl—Ph CN H 2,6-F2—Ph 155.1-157.9
V-65 Q14 2-Cl—Ph CN B45 2,6-F2—Ph 159.3-160.3
V-66 Q14 2-Cl—Ph CN H A7 150-152
V-67 Q14 2-Cl—Ph CN SO2(3-Cl—Ph) A7 132-133
V-68 Q14 PhMe2C CN H A2 vitreous state
V-69 Q14 PhMe2C CN B7 A2 vitreous state
V-70 Q14 PhMe2C CN COCH2OMe A2 vitreous state
V-71 Q15 Ph CN H A1 151-153
V-72 Q16 3-CN—Ph CN H A1 174-175
V-73 Q17 5-CO2Et CN B7 A2 viscous oil
V-74 Q18 3-pyridin- CN H A2 219 (decompo-
2-yl sition)
V-75 Q19 5-Me-2-Ph CN H A2 181-182
V-76 Q19 5-Me-2-Ph CN B7 A2 viscous oil
V-77 Q18 3-pyridin- CN B7 A2 vitreous state
2-yl
V-78 Q18 3-pyridin- CN B46 A2 vitreous state
2-yl
V-79 Q18 t-Bu CN H A2 110.4-110.8
V-80 Q20 6-I CN H A2 205-208
V-81 Q20 6-I CN B7 A2 137-142
V-82 4-Ph- — CN H A2 165.9-166.7
oxazol-2-yl
V-83 4-Ph- — CN B15 A2 vitreous state
oxazol-2-yl
V-84 4-Ph- — CN B7 A2 vitreous state
oxazol-2-yl
V-85 Q19 5-Me-2-Ph CN H A7 117-118
V-86 3-(2-Cl—Ph) — CN H A2 155-156
imidazolin-
2-on-1-yl
*E-form or Z-form
TABLE 20
Figure USRE038188-20030715-C00385
No. G B Y1 Y2 melting point (° C.)
VI-4 tBu B33 H Me 93.7-96.6
VI-5 tBu Et Me H resinous
VI-6 tBu B33 Me H resinous
VI-7 tBu Me Me Me resinous
VI-8 tBu Et Me Me resinous
VI-9 tBu B3 Me Me resinous
VI-10 tBu B3 Me Me resinous
(isomer of VI-9)
VI-11 tBu CH2OCH2Ph Me Me resinous
VI-12 tBu CH2OCH2Ph Me Me resinous
(isomer of VI-11)
VI-13 tBu B24 Me Me resinous
VI-14 tBu B32 Me Me resinous
VI-15 tBu B32 Me Me resinous
(isomer of VI-14)
VI-16 tBu B33 Cl Me 66.5-67.45
VI-17 tBu B33 Me Br 94.0-95.0
VI-18 tBu Et H Me 133.0-135.5
VI-19 tBu B33 Me Me resinous
(Z-form)
VI-20 tBu B33 Me Me resinous
VI-21 tBu H Me H resinous
VI-22 tBu H H Me resinous
VI-23 tBu H Me Me resinous
VI-24 tBu H Cl Me 68.0-69.0
VI-25 tBu H Me Br resinous
VI-26 sBu H Me Me resinous
VI-27 EtMe2C H Me Me resinous
VI-28 EtMe2C H Cl Me resinous
VI-29 tBu B7 Me Me 102.2-103.8
VI-30 tBu B6 Me Me resinous
VI-31 tBu CO(2-MeO—Ph) Me Me resinous
VI-32 tBu B26 Me Me resinous
VI-33 tBu B7 Cl Me resinous
VI-34 tBu COOiBu Me Me resinous
VI-35 EtMe2C B7 Me Me resinous
VI-36 sBu B7 Me Me resinous
VI-37 tBu CO(2-MeO—Ph) Cl Me 181.5-182.5
VI-38 tBu B7 —(CH2)3— 105.3-106.8
VI-39 tBu B7 MeO Me 68.1-70.6
VI-40 tBu B7 Me H resinous
VI-41 tBu CO(2-Me—Ph) Cl Me 128.0-130.0
VI-42 tBu CO(3-pyridyl) Me Me resinous
VI-43 tBu CO(2-Cl—Ph) Me Me 133.0-134.0
VI-44 tBu CO(2-Cl—Ph) Me Me 150.0-151.0
(Isomer of I-43)
VI-45 tBu B7 Me Br 118.0-119.0
VI-46 tBu CO(3-Cl—Ph) Me Me 143.0-145.0
VI-47 tBu CO(4-Cl—Ph) Me Me 169.0-170.0
VI-48 tBu B5 Me Me resinous
VI-49 tBu B2 Me Me 110.6-111.8
VI-50 tBu CO(2-Me—Ph) Me Me 127.0-128.0
VI-51 tBu CO(3-Me—Ph) Me Me 111.0-112.0
VI-52 tBu CO(4-Me—Ph) Me Me 134.5-136.0
TABLE 21
Figure USRE038188-20030715-C00386
melting point ° C.
No. B Y1 Y2 (ratio of isomer)
VII-1 H H H pale brown
solid
VII-2 H H Me >200
(hydrochloride)
VII-3 H Me H 86.2-88.1
VII-4 H Cl Me resinous
VII-5 H H Cl resinous
VII-6 H Cl Et resinous
VII-7 H Me Me 207-210
VII-8 H —(CH2)3— resinous
VII-9 Me Me Me resinous
VII-10 CH2Ph Me Me resinous
VII-11 B7 Me Me 133.7-134.5
(Z-form)
VII-12 B7 Me Me resinous
(E-form)
VII-13 B7 H Me resinous (3/2)
VII-14 B7 H Cl resinous (20/1)
VII-15 B7 Me H resinous
VII-16 B7 Cl Me resinous (20/1)
VII-17 B7 Cl Et resinous (10/1)
VII-18 B6 Cl Me resinous (=3/1)
VII-19 B36 Cl Me resinous (5/1)
VII-20 B7 —(CH2)3— resinous (5/1)
VII-21 B15 Me Me resinous (10/1)
VII-22 CO-cPen Me Me resinous (10/1)
VII-23 B8 Me Me resinous (10/1)
VII-24 B6 Me Me resinous (10/1)
VII-25 CO(4-Me—Ph) Me Me resinous (10/1)
VII-26 B40 Me Me resinous (10/1)
VII-27 CO(2-MeO—Ph) Me Me resinous (10/1)
VII-29 B38 Me Me resinous (10/1)
VII-30 B36 Me Me resinous (10/1)
VII-31 B35 Me Me resinous (10/1)
VII-32 B37 Me Me resinous (10/1)
VII-33 B5 Me Me resinous (10/1)
VII-34 SO2Ph Me Me resinous (10/1)
VII-35 SO2(4-Me—Ph) Me Me resinous (10/1)
VII-36 SO2(4-CF3—Ph) Me Me resinous (10/1)
VII-37 SO2(2,4,6-Me3—Ph) Me Me resinous (10/1)
VII-38 B23 Me Me resinous (10/1)
VII-39 Et Me Me resinous (7/1)
VII-40 B7 H CF3 resinous
VII-41 B7 H H resinous (2/1)
VII-42 H Cl MeO 149.6-151.2
VII-43 B7 Cl MeO resinous
VII-44 H MeO Me resinous
VII-45 H MeO Me resinous
TABLE 22
Figure USRE038188-20030715-C00387
melting
No. Q R B A point ° C.
VIII-1 Q21 Ph H A2 165.9-166.7
VIII-2 Q21 Ph B15 A2 resinous
VIII-3 4-tBu—Ph — CH2O(4-Cl—Ph) A1 resinous
VIII-4 Q19 5-Me-2-Ph H A7 117.0-118.0
VIII-5 Q7 5-CF3 H A38 74.0-77.0
VIII-6 4-tBu—Ph — B7 A48 145.0-146.0
VIII-7 Q19 5-Me-2-Ph B3 A7 117.0-122.0
VIII-8 Q23 cHex H A13 resinous
VIII-9 Q23 tBu SO2(3-Cl—Ph) A13 resinous
VIII-10 Q23 1-naphtyl H A13 145.0-146.0
VIII-11 Q8 4-Cl—Ph H A2 212.0-214.0
VIII-12 Q24 2-pyridyl B7 A2 182.0-183.0
VIII-13 3-Cl-4-CHF2O—Ph — B7 A2 resinous
VIII-14 Q22 tBu CONMe2 A13 98.0-100.0
VIII-15 Q24 tBu B7 A2 80.0-92.0
VIII-16 Q22 2-pyridyl B7 A2 133.0-134.0
VIII-17 Q19 5-Me-2-Ph B7 A7 85.0-102.0
VIII-18 Q10 5-Me-1-(2-pyridyl) H A2 139.0-142.0
VIII-19 Q22 1-Me-cHex H A13 98.0-99.0
VIII-20 Q14 PhMe2C B6 A13 resinous
VIII-21 Q22 tBu B2 A13 resinous
VIII-22 Q22 nPen H A13 resinous
VIII-23 Q25 4-I H A13 177.5-178.2
VIII-24 Q25 4-I B7 A2 resinous
VIII-25 Q22 tBu B7 A39 resinous
VIII-26 Q22 nNon H A13 resinous
VIII-27 Q22 C17H35 H A13 resinous
VIII-28 Q22 cPr H A13 88.8-89.7
VIII-29 Q22 cPen B6 A13 resinous
VIII-30 Q22 PhMeCH H A13 resinous
VIII-31 Q22 nPrMe2C H A13 resinous
VIII-32 Q25 2-pyridyl H A41 261.0-262.0
VIII-33 Q25 4-COOMe B7 A2 97.0-98.0
VIII-34 Q22 CH2═CHCH2CHMe H A13 resinous
VIII-35 Q22 3-Me-cHex H A13 resinous
VIII-36 Q22 4-Me-CHex H A13 resinous
VIII-37 Q22 2-Me-cPr H A13 resinous
VIII-38 Q22 sBu H A13 resinous
VIII-39 Q26 tBu H A13 134.3-135.7
VIII-40 Q22 Et2CH H A13 74.0-75.0
VIII-41 Q22 nPr2CH H A13 resinous
VIII-42 Q22 2-Me-cHex B6 A13 resinous
VIII-43 Q22 cHep H A13 resinous
VIII-44 Q25 2-pyridyl H A42 270.0-272.0
VIII-45 Q22 2,3-(MeO)2—Ph B7 A13 resinous
VIII-46 Q22 2-EtO—Ph B7 A13 131.3-132.6
VIII-47 Q25 3-(2-pyridyl) H A21 resinous
VIII-48 Q25 3-(2-pyridyl) B7 A14 84.0-85.0
VIII-49 Q25 3-(2-pyridyl) H A43 186.9-188.3
VIII-50 Q25 3-COOEt B7 A2 resinous
VIII-51 Q22 2,4-Cl2—Ph H A13 137.5-138.5
VIII-52 Q22 2-Ph—Ph H A13 112.0-113.0
VIII-53 Q19 2-Ph H A10 232.5-235.6
VIII-54 Q19 2-Ph B7 A10 resinous
VIII-55 Q25 5-(2-pyridyl) B7 A10 resinous
VIII-56 Q25 3-COOiPr H A2 130.0-131.0
VIII-57 Q25 3-(2-pyridyl) H 4-NH2- 114.3-117.5
2-F—Ph HCl
VIII-58 Q25 3-(2-pyridyl) B7 A22 resinous
VIII-59 Q25 3-(2-pyridyl) B7 A44 resinous
VIII-60 Q25 3-(2-pyridyl) H A18 resinous
VIII-61 Q25 3-(2-pyridyl) B7 A7 resinous
VIII-62 Q25 3-CN B7 A45 resinous
VIII-63 Q25 3-(2-pyridyl) B7 A49 resinous
VIII-64 Q25 3-(2-pyridyl) H A50 143.2-147.6
VIII-65 Q25 3-(2-pyridyl) B7 A30 116.0-117.0
VIII-66 Q25 3-COOiPr B7 A45 resinous
VIII-67 Q25 3-(4-pyridyl) H A45 resinous
VIII-68 Q25 3-(2-pyridyl) B7 A46 140.7-144.5
VIII-69 4-tBu—Ph — B7 A42 resinous
VIII-70 Q25 3-(2-thienyl) H A47 resinous
VIII-71 Q22 cHep H A47 resinous
VIII-72 Q22 cHep B7 A47 resinous
VIII-73 4-tBu—Ph — B6 A42 resinous
VIII-74 4-tBu—Ph — B33 A42 62.0-63.0
VIII-75 Q22 tBu B33 A47 resinous
VIII-76 Q27 2-pyridyl B7 A45 144.0-145.0
VIII-77 Q27 2-pyridyl H A45 170.0-171.0
VIII-78 Q27 2-pyridyl B7 A42 180.0-181.0
VIII-79 Q28 2-pyridyl H A45 resinous
VIII-80 Q28 2-pyridyl B7 A45 resinous
VIII-81 Q19 5-Me-2-Ph H A47 resinous
VIII-82 Q19 5-Me-2-Ph B7 A47 139.2-141.6
VIII-83 Q25 3-tBu-4-COOMe B7 A47 115.0-116.0
VIII-84 Q22 EtMe2C B7 A47 resinous
VIII-85 Q27 2-pyridyl H A3 139.0-140.0
VIII-86 4-tBu—Ph — B7 A49 93.6-95.2
VIII-87 Q9 1-(2-pyridyl) H A47 resinous
VIII-88 Q9 5-MeO-1-(2-pyridyl) H A47 resinous
VIII-89 4-tBu—Ph — H A21 123.0-124.0
VIII-90 Q29 tBu B7 A47 resinous
VIII-91 Q22 iBu B7 A2 73.0-74.0
VIII-92 Q22 iBu H A2 62.0-63.0
VIII-93 4-tBu—Ph — B7 A14 98.0-99.0
VIII-94 Q22 tBu B33 A52 92.0-93.0
Formulation Examples
Now, Formulation Examples of pesticides comprising the compounds of the present invention as the active ingredient are shown below, which, however, are not intended to restrict the scope of the invention. In the following Formulation Examples, “part” or “parts” are by weight.
[Formulation Example 1] Wettable Powder:
Compound No. I-1 of the invention 50 parts
Zeeklite PFP (trade name, kaolin-type clay 43 parts
manufactured by Zeeklite Mining Industries,
Co., Ltd.)
Solpol 5050 (trade name, anionic surfactant 2 parts
manufactured by Toho Chemical Co., Ltd.)
Runox 1000C (trade name, anionic surfactant 3 parts
manufactured by Toho Chemical Co., Ltd.)
Carplex #80 (anti-caking agent, trade name, 2 parts
white carbon manufactured by Shionogi
Pharmaceutical Co., Ltd.)
The above-mentioned components were homogeneously mixed and ground to form a wettable powder.
[Formulation Example 2] Emulsion:
Compound No. I-1 of the Invention 3 parts
Methylnaphthalene 76 parts
Isophorone 15 parts
Solpol 3005X (trade name, mixture of 6 parts
nonionic surfactant and anionic surfactant
manufactured by Toho Chemical Co., Ltd.)
The above-mentioned components were homogeneously mixed to form an emulsion.
[Formulation Example 3] Flowable:
Compound No. I-1 of the invention 35 parts
Agrisol S-711 (trade name, nonionic surfactant 8 parts
manufactured by Kao Corp.)
Runox 1000C (trade name, anionic surfactant 0.5 part
manufactured by Toho Chemical Co., Ltd.)
Aqueous solution of 1% Rhodopol (trade name, 20 parts
thickener manufactured by Rhone-Poulenc)
Ethylene glycol (freezing inhibitor) 8 parts
Water 28.5 parts
The above-mentioned components were homogeneously mixed to prepare a flowable.
[Formulation Example 4] Granular wettable powder
(Dry flowable):
Compound No. I-1 of the invention 75 parts
Isoban No. 1 (trade name, anionic surfactant 10 parts
manufactured by Kuraray Isoprene Chemical
Co., Ltd.)
Vanilez N (trade name, anionic surfactant 5 parts
manufactured by Sanyo Kokusaku Pulp
Co., Ltd.)
Carplex #80 (trade name, white carbon 10 parts
manufactured by Shionogi Pharmaceutical
Co., Ltd.)
The above-mentioned components were homogeneously mixed and finely ground to form a dry flowable.
[Formulation Example 5] Granules:
Compound No. I-1 of the invention 0.1 part
Bentonite 55.0 parts
Talc 44.9 parts
The above-mentioned components were homogeneously mixed and ground, to which was added a small amount of water, stirred, mixed and kneaded. The resulting mixture was granulated and dried into granules, using an extrusion granulator.
[Formulation Example 6] Dust:
Compound No. I-1 of the invention 3.0 parts
Carplex #80 (trade name, white carbon 0.5 part
manufactured by Shionogi Pharmaceutical
Co., Ltd.)
Clay 95 parts
Diisopropyl phosphate 1.5 parts
The above-mentioned components were homogeneously mixed and ground to form a dust.
Upon use, the wettable powder, emulsion, flowable and dry flowable are diluted from 50 to 20000 times with water, and applied in an amount of from 0.005 to 50 kg/ha in terms of the active ingredient.
Now, Formulation Examples of agents for preventing the attachment of aquatic organisms of the present invention are shown below, which, however, are not intended to restrict the scope of the invention.
[Formulation Example 7]
Compound No. II-2 of the invention 8 parts
VYHH (vinyl-type synthetic resin 7 parts
manufactured by UCC Co., Ltd.)
Rosin 7 parts
Tricresyl phosphate 3 parts
Talc 20 parts
Barium sulfate 15 parts
Red iron oxide 10 parts
Xylene 20 parts
Methyl isobutyl ketone 10 parts
The above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms of the invention. This agent can be used as a coating paint.
[Formulation Example 8]
Compound No. II-2 of the invention 5 parts
CR-10 (chlorine rubber resin manufactured 13 parts
by Asahi Denka KK)
Zinc flower 20 parts
Talc 20 parts
Plasticizer 2 parts
Red iron oxide 10 parts
Xylene 30 parts
The above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms of the invention. This agent can be used as a coating paint.
[Formulation Example 9]
Compound No. II-2 of the invention 8 parts
VYHH (vinyl-type synthetic resin manufactured 7 parts
by UCC Co., Ltd.)
Rosin 7 parts
Tricresyl phosphate 3 parts
Talc 20 parts
Barium sulfate 15 parts
Red iron oxide 10 parts
Xylene 20 parts
Methyl isobutyl ketone 10 parts
The above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms the invention. This agent can be used as a coating paint.
[Formulation Example 10]
Compound No. II-2 of the invention 5 parts
CR-10 (chlorine rubber resin manufactured 13 parts
by Asahi Denka KK)
Zinc flower 20 parts
Talc 20 parts
Plasticizer 2 parts
Red iron oxide 10 parts
Xylene 30 parts
The above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms of the invention. This agent can be used as a coating paint.
TEST EXAMPLES
Now, the following Test Examples are to demonstrate the usefulness of the compounds of the present invention as pesticides.
Test Example 1
Insecticidal Test for Brown Rice Planthopper (Nilaparvata lugens Stal)
A 5% emulsion (or 25% wettable powder) of a compound of the present invention was diluted with water containing a spreading agent to give a 500 ppm solution of the compound.
The stems and leaves of rice-plants in 1/20,000 are pot were sufficiently applied with the resulting solution. After the thus-applied chemical solution was dried in air, each pot was covered with a cylindrical cover. Ten (10) second instar nymphae of brown rice planthoppers (Nilaparvata lugens) were released in each pot. After having been thus covered, the pots were stored in a thermostatic chamber. After 6 days passed, the insects in each pot were observed, and the mortality thereof was determined according to the following equation. Each compound was tested in that manner for two groups of pots.
Mortality (%)=[number of insect killed/(number of insect killed+number of living insect)]×100
In this test, the following compounds exhibited mortality of 80% or more.
Compounds of the invention: Nos. I-2, I-18, I-19, I-23, I-30, I-31, I-32, I-35, I-39, I-42, I-44, I-58, I-59, I-62, I-63, I-70, I-72, I-80, I-106, I-114, I-123, I-137, II-1, II-2, II-3, II-5, II-6, II-12, II-15, II-23, II-25, II-26, II-28, II-33, II-34, II-36, II-37, II-38, II-39, II-43, II-44, II-46, II-53, II-54, II-55, II-61, II-66, II-73, II-74, II-75, II-76, II-80, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-91, II-92, II-93, II-97, II-98, II-111, II-114, II-116, II-134, II-136, II-137, II-154, II-155, II-159, III-1, III-2, III-4, III-6, III-15, III-16, III-17, III-18, III-19, III-21, IV-48, IV-58, V-2, V-12, V-13, V-28, V-48, V-49, V-51, V-53, V-54, V-55, V-56, V-57, V-59, V-60.
Test Example 2
Insecticidal Test for Green Rice Leafhoppers (Nephotettix cincticeps Uhler)
The stems and leaves of plants was dipped in a 500 ppm emulsion of a compound of the invention for about 10 seconds. The thus-treated stems and leaves were put into glass cylinders, into which were released adults of green rice leafhoppers (Nephotettix cincticeps) that were resistant to organic phosphorous insecticides. Each glass cylinder was covered with a perforated cover, and stored in a thermostatic chamber at 25° C. After 6 days passed, the insects in each cylinder were observed, and the mortality of the insects was determined according ot the sme equation as in Test Example 1. Each compound was tested in that manner for two groups of cylinders. In this test, the following compounds exhibited morality of 80% or more.
Compounds of the invention: Nos. I-1, I-2, I-4, I-5, I-8, I-9, I-10, I-19, I-24, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-36, I-39, I-40, I-41, I-42, I-43, I-44, I-47, I-53, I-54, I-55, I-56, I-57, I-58, I-59, I-62, I-63, I-69, I-70, I-71, I-72, I-74, I-79, I-80, I-81, I-115, I-121, I-125, I-127, I-137, II-1, II-2, II-3, II-5, II-6, II-7, II-9, II-10, II-11, II-12, II-13, II-15, II-23, II-26, II-28, II-33, II-34, II-36, II-38, II-37, II-43, II-46, II-49, II-52, II-54, II-55, II-63, II-64, II-65, II-66, II-67, II-68, II-69, II-73, II-74, II-75, II-76, II-77, II-78, II-79, II-80, II-81, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-91, II-92, II-93, II-97, II-98, II-99, II-107, II-111, II-116, II-117, II-130, II-131, II-132, II-134, II-136, II-137, II-142, II-145, II-153, II-154, II-1, III-2, III-3, III-4, III-5, III-6, III-13, III-15, III-16, III-17, III-18, III-19, III-20, III-21, IV-32, IV-58, V-2, V-12, V-13, V-14, V-38, V-41, V-43, V-48, V-49, V-51, V-53, V-54, V-55, V-56, V-57, V-59, V-60, V-75.
Test Example 3
Insecticidal Test for Green Peach Aphids (Myzus persicae Sulzer)
Moistured filter paper was placed in each laboratory glass dish having an inner diameter of 3 cm, and a leaf cabbage having the same diameter as that of the dish was put on the filter paper. Four female, apterous adults of green peach aphids (Myzus persicae) were put on the cabbage leaf. Following day, a chemical sample (2.5 mg/cm2) was sprayed over the dishes, using a rotary sprinkler. The chemical solution herein was prepared by diluting a 5% emulsion (or 25% wettable powder) of a compound of the invention to 500 ppm with water containing a spreading agent. After 6 days passed, the insects in each cylinder were observed, and mortality of the insects (larvae and adults) was determined according to the following equation. Each compound was tested in that manner for two groups of dishes.
Mortality (%)=[number of insect killed/(number of insect killed+number of living insect)]×100
In this test, the following compounds exhibited mortality of 80% or more.
Compounds of the invention: Nos. I-1, I-2, I-3, I-4, I-5, I-7, I-8, I-10, I-11, I-12, I-13, I-14, I-16, I-17, I-18, I-19, I-21, I-22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30, I-31 I-32, I-33, I-34, I-35, I-36, I-37, I-38, I-40, I-41, I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-51, I-52, I-53, I-54, I-55, I-56, I-57, I-58, I-59, I-62, I-63, I-69, I-70, I-71, I-72, I-73, I-74, I-76, I-77, I-78, I-79, I-80, I-81, I-84, I-85, I-86, I-89, I-90, I-92, I-96, I-97, I-104, I-108, I-125, I-136, I-137, I-138, II-2, II-3, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-15, II-16, II-17, II-23, II-24, II-24, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-43, II-44, II-50, II-52, II-53, II-54, II-55, II-58, II-60, II-63, II-64, II-65, II-66, II-68, II-69, II-70, II-71, II-73, II-74, II-75, II-76, II-78, II-79, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-97, II-98, II-99, II-101, II-102, II-105, II-107, II-111, II-116, II-117, II-118, II-121, II-130, II-131, II-132, II-133, II-134, II-136, II-137, II-138, II-140, II-141, II-142, II-151, II-153, II-154, II-159, II-160, III-1, III-2, III-3, III-4, III-5, III-6, III-15, III-16, III-17, III-18, III-19, III-20, III-21, IV-10, IV-11, IV-21, IV-23, IV-45, V-1, V-2, V-10, V-11, V-12, V-13, V-14, V-28, V-31, V-32, V-41, V-45, V-48, V-49, V-50, V-51, V-52, V-53, V-54, V-55, V-56, V-57, V-59, V-60, V-73, V-75, VII-1, VII-2, VII-3, VII-4, VII-5, VII-6, VII-7, VII-8, VII-9, VII-10, VII-11, VII-12, VII-13, VII-14, VII-15, VII-16, VII-17, VII-18, VII-19, VII-20, VII-21, VII-22, VII-23, VII-24, VII-25, VII-26, VII-27, VII-28, VII-29, VII-30, VII-31, VII-32, VII-33, VII-34, VII-35, VII-36, VII-37, VII-38, VII-39, VII-40, VII-41, VII-42, VII-43, VII-44, VII-45, VIII-12, VIII-32, VIII-42, VIII-47, VIII-49, VIII-55, VIII-57, VIII-58, VIII-61, VIII-64, VIII-65, VIII-67, VIII-85.
Test Example 4
Insecticidal Test for Diamond Back Moth (Plutella xylostella Linne)
The leaves of cabbage were dipped in a 500 ppm aqueous emulsion of a compound of the invention for about 10 seconds. After having been dried in air, the thus-treated leaves were put into laboratory dishes. Ten (10) second larvae of diamond back moth (Plutella xylostella) were released in each dish. Each dish was covered with a perforated cover, and stored in a thermostatic chamber at 25° C. After 6 days passed, the insects in each dish were observed, and mortality of the insects was obtained according to the same equation as in Test Example 1. Each compound was tested in that manner for two groups of dishes. In this test, the following compounds exhibited mortality of 80% or more.
Compounds of the invention: Nos. I-1, I-2, I-4, I-5, I-6, I-8, I-9, I-10, I-13, I-18, I-19, I-29, I-30, I-31, I-33, I-34, I-35, I-36, I-38, I-39, I-40, I-41, I-43, I-44, I-45, I-46, I-47, I-51, I-52, I-53, I-56, I-57, I-58, I-59, I-62, I-63, I-70, I-71, I-72, I-73, I-74, I-76, I-77, I-78, I-79, I-80, I-81, I-84, I-86, I-89, I-96, I-97, I-99, I-104, I-106, I-114, I-125, I-137, II-1, II-2, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-15, II-17, II-23, II-24, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-40, II-41, II-42, II-43, II-54, II-55, II-58, II-60, II-61, II-62, II-63, II-64, II-65, II-66, II-67, II-68, II-69, II-70, II-71, II-72, II-73, II-74, II-75, II-76, II-77, II-78, II-79, II-80, II-81, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-94, II-97, II-98, II-99, II-100, II-101, II-105, II-106, II-107, II-108, II-109, II-110, II-111, II-116, II-117, II-118, II-121, II-122, II-155, II-159, II-161, II-1, III-2, III-3, III-4, III-5, III-6, III-7, III-9, III-10, III-11, III-13, III-14, III-15, III-16, III-17, III-18, III-19, III-20, III-21, IV-7, IV-8, IV-29, IV-47, IV-53, IV-58, V-1, V-2, V-11, V-12, V-13, V-29, V-37, V-41, V-43, V-46, V-48, V-50, V-51, V-52, V-53, V-54, V-55, V-56, V-57, V-58, V-59, V-60, V-64, V-75.
Test Example 5
Insecticidal Test for Cucurbit Leaf Beetles (Aulacophora femoralis Motschulsky)
A 5% emulsion (or 25% wettable powder) of a compound of the present invention was diluted with water containing a spreading agent to give a 500 ppm solution of the compound. The leaves of cucumbers were dipped in this chemical solution for about 10 seconds, dried in air, and put into a laboratory dish. Ten (10) second instar nymphae of cucur-bit leaf beetles (Aulacophora femoralis) were released in each dish. Each dish was covered with a cover, and stored in a thermostatic chamber at 25° C. After 6 days passed, the insects in each dish were observed, and mortality of the insects was determined according to the same equation as in Test Example 1. Each compound was tested in that manner for two groups of dishes.
In this test, the following compounds exhibited mortality of 100%.
Compounds of the invention: Nos. I-1, I-2, I-4, I-6, I-8, I-9, I-10, I-11, I-12, I-13, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-39, I-40, I-41, I-43, I-44, I-46, I-53, I-54, I-55, I-56, I-57, I-58, I-59, I-61, I-62, I-63, I-69, I-70, I-71, I-72, I-74, I-76, IU-77, I-78, I-79, I-80, I-81, I-82, I-83, I-92, I-101, I-103, I-104, I-108, I-109, I-124, I-127, I-128, II-1, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-14, II-15, II-16, II-17, II-23, II-24, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-41, II-42, II-43, II-47, II-50, II-53, II-54, II-55, II-57, II-58, II-61, II-62, II-63, II-65, II-66, II-99, II-101, II-102, II-104, II-105, II-106, II-107, II-108, II-109, II-110, II-114, II-122, II-124, II-125, II-131, II-132, II-133, II-134, II-136, II-137, II-139, II-140, II-141, II-142, II-153, II-154, III-1, III-2, III-3, II-4, III-5, III-6, III-9, III-10, III-11, III-12, III-14, III-15, III-16, III-17, III-20, IV-6, IV-13, IV-33, IV-39, IV-56, IV-60, IV-61, IV-72, IV-82, V-1, V-2, V-11, V-12, V-13, V-17, V-22, V-26, V-27, V-29, V-37, V-40, V-42, V-48, V-49, V-50, V-51, V-52, V-54, V-55, V-57, V-59, V-60, V-61, V-64, V-75.
Test Example 6
Acaricidal Test for Two-spotted Spider Mites (Tetranychus urticae Koch)
The leaves of kidney bean plants were punched into 3 cm-diameter discs, using a leaf punch, and put onto moistured filter paper in a 7 cm-diameter styrol cup. Ten (10) larvae of two-spotted spider mites (Tetranychus urticae) were put to each leaf. A 5% emulsion (or 25% wettable powder) of a compound of the invention was diluted with water containing a spreading agent to give a 500 ppm solution of the compound. The solution was sprayed over each cup in an amount of 2 ml/cup, using a rotary sprinkler, and the cups were stored in a thermostatic chamber at 25° C. After 96 hours passed, the mites in each cup were observed, and mortality of the mites was determined according to the same equation as in Test Example 1. Each compound was tested in that manner for two groups of cups.
In this test, the following compounds exhibited the mites at a percentage of 80% or more.
Compounds of the invention: Nos. I-1, I-2, I-3, I-4, I-5, I-7, I-8, I-9, I-10, I-12, I-13, I-19, I-24, I-25, I-26, I-27, I-28, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-36, I-38, I-40, I-41, I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-50, I-51, I-52, I-55, I-56, I-57, I-58, I-59, I-60, I-61, I-62, I-63, I-70, I-71, I-72, I-74, I-76, I-80, I-94, I-95, I-96, I-97, I-99, I-101, I-102, I-103, I-104, I-105, I-106, I-108, I-109, I-110, I-111, I-112, I-113, I-114, I-115, I-117, I-118, I-119, I-122, I-123, I-124, I-125, I-126, I-127, I-128, I-137, II-2, II-3, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-15, II-16, II-17, II-23, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-40, II-41, II-42, II-43, II-45, II-46, II-47, II-48, II-50, II-52, II-53, II-54, II-55, II-58, II-59, II-60, II-61, II-63, II-64, II-65, II-66, II-67, II-68, II-69, II-70, II-71, II-72, II-73, II-74, II-75, II-76, II-77, II-78, II-79, II-80, II-81, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-95, II-97, II-98, II-99, II-101, II-102, II-103, II-105, II-106, II-107, II-108, II-109, II-110, II-111, II-116, II-117, II-118, II-133, II-134, II-136, II-137, II-151, II-153, II-154, II-155, II-159, II-160, II-161, II-173, III-3, III-4, III-5, III-6, III-7, III-9, III-10, III-11, III-12, III-15, III-17, III-18, III-19, III-21, IV-1, IV-2, IV-3, IV-4, IV-5, IV-7, IV-10, IV-11, IV-12, IV-13, IV-14, IV-16, IV-17, IV-18, IV-19, IV-20, IV-21, IV-22, IV-24, IV-25, IV-26, IV-28, IV-29, IV-33, IV-35, IV-36, IV-39, IV-40, IV-41, IV-42, IV-43, IV-44, IV-45, IV-46, IV-47, IV-48, IV-49, IV-50, IV-51, IV-54, IV-55, IV-56, IV-58, IV-59, IV-60, IV-61, IV-62, IV-63, IV-64, IV-65, IV-66, IV-67, IV-68, IV-69, IV-70, IV-71, IV-72, IV-74, IV-75, IV-76, IV-79, IV-80, IV-82, IV-94, IV-95, IV-96, IV-99, IV-100, IV-101, IV-102, IV-109, IV-110, IV-111, IV-112, V-1, V-2, V-3, V-4, V-5, V-6, V-7, V-8, V-10, V-11, V-12, V-13, V-14, V-15, V-16, V-17, V-19, V-23, V-24, V-25, V-26, V-28, V-31, V-36, V-37, V-38, V-40, V-41, V-42, V-43, V-44, V-46, V-47, V-48, V-59, V-60, V-73, V-75, VI-1, VI-2, VI-3, VI-4, VI-5, VI-6, VI-7, VI-87, VI-9, VI-10, VI-11, VI-12, VI-13, VI-14, VI-15, VI-16, VI-17, VI-18, VI-19, VI-20, VI-21, VI-22, VI-23, VI-24, VI-25, VI-29, VI-30, VI-31, VI-32, VI-33, VI-34, VI-35, VI-36, VI-37, VI-38, VI-39, VI-40, VI-41, VI-42, VI-43, VI-44, VI-45, VI-46, VI-47, VI-48, VI-49, VI-50, VI-51, VI-52, VII-1, VIII-2, VIII-4, VIII-6, VIII-7, VIII-8, VIII-9, VIII-10, VIII-13, VIII-14, VIII-15, VIII-16, VIII-17, VIII-18, VIII-19, VIII-20, VIII-21, VIII-22, VIII-23, VIII-24, VIII-26, VIII-27, VIII-28, VIII-29, VIII-30, VIII-31, VIII-33, VIII-34, VIII-35, VIII-36, VIII-37, VIII-38, VIII-39, VIII-40, VIII-41, VIII-43, VIII-44, VIII-45, VIII-46, VIII-48, VIII-50, VIII-51, VIII-52, VIII-53, VIII-54, VIII-56, VIII-59, VIII-60, VIII-63, VIII-66, VIII-69, VIII-70, VIII-71, VIII-72, VIII-73, VIII-74, VIII-75, VIII-76, VIII-77, VIII-78, VIII-81, VIII-82, VIII-83, VIII-84, VIII-86, VIII-87, VIII-89, VIII-90, VIII-91, VIII-92, VIII-93.
Test Example 7
Test for Preventing Leaf Rust, Brown Rust (Puccinia recondita ex Desmaziére)
A chemical solution obtained by diluting an emulsion of a compound of the invention to 500 ppm with water was sprayed on wheat plants (Norin No. 61) grown to 1.5- to 2.0-leaf in a pot having a diameter of 5.5 cm-diameter at a dose of 20 ml/pot using a spraygun.
The following day, a spore suspension (2×105 spore/ml) of leaf rust (brown rust) (Puccinia recondite) was sprayed over the plant-pots were placed overnight in an inoculation box having a temperature of 25° C. and a humidity of 95% or more. Then, the pots were put in a green house. After 7 days of the inoculation, a ratio of an infected and spored area formed to the leaf inoculated was measured, and a preventive value was calculated according to the following equation.
Preventive value=[1−(infected and spotted area ratio in treated region/infected and spotted area ratio in untreated region)]×100
In this test, the following compounds had an protective value of from 70 to 100.
Compounds of the invention: Nos. I-9, I-108, I-127, I-128, II-14, II-15, IV-2, IV-7, V-15, V-10.
With the long-term use of insecticides and microbicides, recently, some pests have become resistant to chemicals and are often difficult to exterminate with conventional insecticides and microbicides. In addition, some insecticides are highly toxic and are prone to remain long, without being decomposed, to destroy the ecosystem. Accordingly, the present invention provides novel, non-toxic and non-persistent insecticides and fungicides, and provides agents for preventing the attachment of aquatic organisms having few influences on the ecosystem and causing little secondary pollution.

Claims (39)

We claim:
1. Ethylene derivatives of a formula:
Figure USRE038188-20030715-C00388
wherein:
Q represents a 1,2,3-triazolyl group optionally substituted by R;
A represents a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, wherein said heterocyclic group is selected from the group consisting of a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl, and quinazolinyl groups;
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3SCH2, CH3OC2H4OCH2, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C4 alkyl group substituted by a benzoyl group optionally substituted by a halogen or a C1-C4 alkyl group, a tetrahydropyranyl group, (CH3) Si, a C1-C4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C1-C4 alkyl group, —SO2CF3, a C1-C4 monoalkylaminosulfonyl group, a C2-C8 dialkylaminosulfonyl group, a phenylaminosulfonyl group, a C2-C5 monoalkylaminothiocarbonyl group, a C3-C9 dialkylaminothiocarbonyl group, a C2-C5 cyanoalkyl group, a C3-C9 alkoxycarbonylalkyl group, —C(═O)T1, —P(═O)T2T3, —P(═S)T2T3, an alkali metal atom, an alkaline earth metal atom, or NHT4T5T6;
E represents CN;
R is a substituent selected from the group consisting of a halogen atom, a C1-C10 alkyl group, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C6 halocycloalkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, a C1-C6 alkoxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C1-C4 haloalkoxy group, a C2-C6 haloalkenyloxy group, a C2-C6 haloalkynyloxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C2-C6 alkenylsulfenyl group, a C2-C6 alkenylsulfinyl group, a C2-C6 alkenylsulfonyl group, a C2-C6 alkynylsulfenyl group, a C2-C6 alkynylsulfinyl group, a C2-C6 alkynylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, a C2-C6 haloalkenylsulfenyl group, a C2-C6 haloalkenylsulfinyl group, a C2-C6 haloalkenylsulfonyl group, a C2-C6 haloalkynylsulfenyl group, a C2-C6 haloalkynylsulfinyl group, a C2-C6 haloalkynylsulfonyl group, NO2, CN, —NU1U2, a phenoxy group, OH, a naphthyl group, a C2-C7 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a C2-C4 alkylcarbonyl group, a C2-C5 alkylcarbonyloxy group, a C2-C5 haloalkylcarbonyloxy group, a benzoyl group optionally substituted by X, a phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, a thienyl group optionally substituted by X, and —N═CT7T8, provided that when the substituent is two or more, then said substituents may be the same or different, and the number of the substituent, R, is 1 or 2, or R is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring;
Y is a substituent selected from the group consisting of a halogen atom, a C1-C10 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C1-C4 haloalkoxy group, a C2-C6 haloalkenyloxy group, a C2-C6 haloalkynyloxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C2-C6 alkenylsulfenyl group, a C2-C6 alkenylsulfinyl group, a C2-C6 alkenylsulfonyl group, a C2-C6 alkynylsulfenyl group, a C2-C6 alkynylsulfinyl group, a C2-C6 alkynylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, a C2-C6 haloalkenylsulfenyl group, a C2-C6 haloalkenylsulfinyl group, a C2-C6 haloalkenylsulfonyl group, a C2-C6 haloalkynylsulfenyl group, a C2-C6 haloalkynylsulfinyl group, a C2-C6 haloalkynylsulfonyl group, NO2, CN, —NU1U2, OH, a C2-C7 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a C2-C5 alkylcarbonyloxy group, a C2-C5 haloalkylcarbonyloxy group, a C3-C7 dialkylaminocarbonyloxy group, a phenyl group optionally substituted by X, and —N═CT7T8, provided that when the substituent is two or more, then said substituents may be the same or different, and the number of the substituent, Y, is 1, 2, 3 or 4, or Y is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8- membered ring;
W is a substituent selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-Chaloalkylsulfonyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkenyloxy group, a C2-C4 haloalkenyloxy group, a C2-C4 alkenylsulfenyl group, a C2-C4 alkenylsulfinyl group, a C2-C4 alkenylsulfonyl group, a C2-C4 haloalkenylsulfenyl group, a C2-C4 haloalkenylsulfinyl group, a C2-C4 haloalkenylsulfonyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C2-C4 alkynyloxy group, a C2-C4 haloalkynyloxy group, a C2-C4 alkynylsulfenyl group, a C2-C4 alkynylsulfinyl group, a C2-C4 alkylnylsulfonyl group, a C2-C4 haloalkynylsulfenyl group, a C2-C4 haloalkynylsulfinyl group, a C2-C4 haloalkynylsulfonyl group, NO2, CN, a formyl group, a C2-C6 alkoxycarbonyl group, a C2-C6 alkylcarbonyl group, a C2-C6 haloalkylcarbonyl group, a C2-C6 alkylcarbonyloxy group, and —NU1U2, provided that when the substituent is two or more, then said substituents may be the same or different, and the number of the substituent, W, is 1,2, 3 and 4;
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C6 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C3-C6 halocycloalkyl group, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, a cycloalkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a cyclopropyl group substituted by both a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group and a C1-C4 alkyl group, a C3-C4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen or a C1-C4 alkoxy group and a halogen, a cyclopropyl group substituted by both a C2-C4 alkenyl group optionally substituted by a halogen and a C1-C4 alkyl group, a C2-C4 alkenyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a C2-C5 alkenyloxy group, a C3-C6 cycloalkoxy group optionally substituted by a C1-C3 alkyl group, a benzyloxy group, a C2-C5 alkoxycarbonyl group, —NU1U2, a phenylamino group, a phenyl group optionally substituted by Z, a phenoxy group optionally substituted by Z, a phenylthio group optionally substituted by Z, a naphthyl group optionally substituted by Z, or a 5-membered or 6-membered heterocyclic group optionally substituted by Z wherein said heterocyclic group is selected from the group consisting of a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, and 3(2H)-pyridazinone groups;
T2 and T3 each independently represent OH, a phenyl, a C1-C6 alkyl group, a C1-C6 alkoxy group, or a C1-C4 alkylsulfenyl group;
T4, T5 and T6 each independently represent H, a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, or a benzyl group; or any two of T4, T5 and T6 may form, together with the nitrogen atom to which they are bonded, a 5-, 6-, 7- or 8-membered cyclic group optionally containing oxygen, nitrogen and/or sulfur atoms;
X and Z are independently substituents selected from the group consisting of a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylsulfenyl group, a C1-C4 alkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C2-C5 alkenylsulfenyl group, a C2-C5 alkenylsulfinyl group, a C2-C5 alkenylsulfonyl group a C1-C4 haloalkylsulfenyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 haloalkylsulfonyl group, NO2, CN, CHO, OH, —NU1U2, a phenyl group, a phenoxy group, and a C2-C5 alkoxycarbonyl group, provided that when the substituent is two or more, then said substituents may be the same or different, and the number of the substituent, X and Z, is 1,2,3,4 or 5 each;
T7 and T8 each independently represent H, or a phenyl, benzyl, or a C1-C6 alkyl group, or T7 and T8 may, together with the carbon atom to which they are bonded, form a 5-, 6-, 7-, or 8-membered ring;
U1 and U2 each independently represent H, a C1-C6 alkyl, a C2-C5 alkylcarbonyl, phenyl or benzyl group, or U1 and U2 may, together with the nitrogen atom to which they are bonded, form a 5-, 6-, 7-, or 8-membered ring.
2. Ethylene derivatives as claimed in claim 1, wherein:
A represents a phenyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, wherein said heterocyclic group is selected from the group consisting of a thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, and imidazolinyl groups and a naphthyl group optionally substituted by W;
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H4OCH2, a C1-C4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C1-C4 alkyl group, —SO2CF3, a C2-C8 dialkylaminosulfonyl group, a C3-C9 dialkylaminothiocarbonyl group, a C3-C9 alkoxycarbonylalkyl group, —C(═O)T1, —P(═O)T2T3, —P(═S)T2T3, an alkali metal atom, an alkaline earth metal atom, or NHT4T5T6; and
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C6 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C3-C6 halocycloalkyl group, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, a cycloalkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a cyclopropyl group substituted by both a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group and a C1-C4 alkyl group, a C3-C4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen or a C1-C4 alkoxy group and a halogen, a cyclopropyl group substituted by both a C2-C4 alkenyl group optionally substituted by a halogen and a C1-C4 alkyl group, a C2-C4 alkenyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a C2-C5 alkenyloxy group, a C3-C6 cycloalkoxy group optionally substituted by a C1-C3 alkyl group, a benzyloxy group, a C2-C5 alkoxycarbonyl group, a phenyl group optionally substituted by Z, a phenoxy group optionally substituted by Z, a phenylthio group, a naphthyl group, or a 5-membered or 6-membered heterocyclic group optionally substituted by Z wherein said heterocyclic group is selected from the group consisting of a thienyl, furyl, oxazolyl, thiazolyl, pyrazolyl, and pyridinyl groups.
3. Ethylene derivatives as claimed in claim 2, wherein A represents a phenyl group optionally substituted by W, a thiazolyl group optionally substituted by Y, a pyrazolyl group optionally substituted by Y, a pyridinyl group optionally substituted by Y, or a pyrimidinyl group optionally substituted by Y; and
Q is represented by the following formula:
Figure USRE038188-20030715-C00389
4. Ethylene derivatives as claimed in claim 2, wherein:
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H4OCH2, a C1-C4 alkyl sulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C1-C4 alkyl group, or —C(═O)T1; and
Q is represented by the following formula:
Figure USRE038188-20030715-C00390
5. Ethylene derivatives as claimed in claim 4, wherein:
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H40CH2, a C1-C4 alkylsulfonyl group, or —C(═O)T1; and
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a phenyl group optionally substituted by Z, or a pyridinyl group optionally substituted by Z.
6. Ethylene derivatives as claimed in claim 4, wherein R is a substituent selected from the group consisting of a halogen atom, a C1-C10 alkyl group, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, a C1-C6 alkoxy group, CN, a naphthyl group, a C2-C7 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a C2-C4 alkylcarbonyl group, a phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, and a thienyl group optionally substituted by X, and the number of the substituent, R, is 1 or 2.
7. Ethylene derivatives as claimed in claim 6, wherein:
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H4OCH2, a C1-C4 alkylsulfonyl group, or —C(═O)T1; and
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a phenyl group optionally substituted by Z, or a pyridinyl group optionally substituted by Z.
8. Ethylene derivatives as claimed in claim 3, wherein R is a substituent selected from the group consisting of a halogen atom, a C1-C10 alkyl group, a C1-C4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C1-C4 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, a C1-C6 alkoxy group, CN, a naphthyl group, a C2-C7 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a C2-C4 alkylcarbonyl group, a phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, and a thienyl group optionally substituted by X, and the number of the substituent, R, is 1 or 2.
9. Ethylene derivatives as claimed in claim 8, wherein:
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H4OCH2, a C1-C4 alkylsulfonyl group, or —C(═O)T1; and
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a phenyl group optionally substituted by Z, or a pyridinyl group optionally substituted by Z.
10. Ethylene derivatives as claimed in claim 6, wherein R is a substituent selected from the group consisting of a C1-C10 alkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, CN, a naphthyl group, a C2-C7 alkoxycarbonyl group, a C2-C4 alkoxyalkyl group, a phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, and a thienyl group optionally substituted by X, and the number of the substituent, R, is 1 or 2.
11. Ethylene derivatives as claimed in claim 10, wherein:
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H4OCH2, a C1-C4 alkylsulfonyl group, or —C(═O)T1; and
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a phenyl group optionally substituted by Z, or a pyridinyl group optionally substituted by Z.
12. Ethylene derivatives as claimed in claim 10, wherein
A represents a phenyl group optionally substituted by W, a thiazolyl group optionally substituted by Y, a pyrazolyl group optionally substituted by Y, a pyridinyl group optionally substituted by Y, or a pyrimidinyl group optionally substituted by Y.
13. Ethylene derivatives as claimed in claim 12, wherein:
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H4OCH2, a C1-C4 alkylsulfonyl group, or —C(═O)T1; and
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a phenyl group optionally substituted by Z, or a pyridinyl group optionally substituted by Z.
14. Ethylene derivatives as claimed in claim 10, wherein
R is a substituent selected from the group consisting of a C1-C10 alkyl group, a C3-C6 cycloalkyl group optionally substituted by a C1-C3 alkyl group, a C2-C4 alkoxyalkyl group, a phenyl group optionally substituted by X, and a pyridyl group optionally substituted by X, and the number of the substituent, R, is 1 or 2.
15. Ethylene derivatives as claimed in claim 14, wherein:
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H4OCH2, a C1-C4 alkylsulfonyl group, or —C(═O)T1; and
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a phenyl group optionally substituted by Z, or a pyridinyl group optionally substituted by Z.
16. Ethylene derivatives as claimed in claim 14, wherein
A represents a phenyl group optionally substituted by W, a thiazolyl group optionally substituted by Y, a pyrazolyl group optionally substituted by Y, a pyridinyl group optionally substituted by Y, or a pyrimidinyl group optionally substituted by Y.
17. Ethylene derivatives as claimed in claim 16, wherein:
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H4OCH2, a C1-C4 alkylsulfonyl group, or —C(═O)T1; and
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a phenyl group optionally substituted by Z, or a pyridinyl group optionally substituted by Z.
18. Ethylene derivatives as claimed in claim 17, wherein
A represents a pyrazolyl group optionally substituted by Y, or a pyridinyl group optionally substituted by Y.
19. Ethylene derivatives as claimed in claim 14, wherein
R is a substituent selected from the group consisting of a C1-C10 alkyl group, and a phenyl group, and the number of the substituent, R, is 1 or 2.
20. Ethylene derivatives as claimed in claim 19, wherein:
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H4OCH2, a C1-C4 alkylsulfonyl group, or —C(═O)T1; and
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a phenyl group optionally substituted by Z, or a pyridinyl group optionally substituted by Z.
21. Ethylene derivatives as claimed in claim 19, wherein
A represents a phenyl group optionally substituted by W, a thiazolyl group optionally substituted by Y, a pyrazolyl group optionally substituted by Y, a pyridinyl group optionally substituted by Y, or a pyrimidinyl group optionally substituted by Y.
22. Ethylene derivatives as claimed in claim 21, wherein:
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H4OCH2, a C1-C4 alkylsulfonyl group, or —C(═O)T1; and
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C1-C12 alkoxy group, a C1-C4 haloalkoxy group, a phenyl group optionally substituted by Z, or a pyridinyl group optionally substituted by Z.
23. Ethylene derivatives as claimed in claim 21, wherein
A represents a pyrazolyl group optionally substituted by Y or a pyridinyl group optionally substituted by Y.
24. Ethylene derivatives as claimed in claim 23, wherein:
B represents H, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkoxyalkyl group, CH3OC2H4OCH2, a C1-C4 alkylsulfonyl group, or —C(═O)T1; and
T1 represents a C1-C20 alkyl group, a C2-C6 alkenyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy-C1-C4 alkyl group, a C1-C12 alkoxy group, or a C1-C4 haloalkoxy group.
25. Ethylene derivatives as claimed in claim 24, wherein:
A is a heterocyclic group optionally substituted by Y, said heterocyclic group being a pyrazolyl or pyridinyl group;
B is H, a C2-C4 alkoxyalkyl group, or —C(═O)T1;
Y is a substituent selected from the group consisting of a halogen atom, a C1-C10 alkyl group, and a C1-C6 haloalkyl group, and the number of the substituent, Y, is 1, 2, or 3;
T1 is a C1-C20 alkyl group.
26. Ethylene derivatives as claimed in claim 1, wherein Q is represented by the following formula:
Figure USRE038188-20030715-C00391
27. Ethylene derivatives as claimed in claim 26, wherein the ethylene derivative is represented by the following formula:
Figure USRE038188-20030715-C00392
wherein R represents a C1-C6 alkyl group.
28. Ethylene derivatives as claimed in claim 26, wherein
R is selected from the group consisting of 5-methyl-2-phenyl, 5-ethyl-2-phenyl, and 5-isopropyl-2-phenyl.
29. Ethylene derivatives as claimed in claim 1, wherein A is selected from the group consisting of:
Figure USRE038188-20030715-C00393
30. Ethylene derivatives as claimed in claim 1, wherein B is
Figure USRE038188-20030715-C00394
31. Ethylene derivatives as claimed in claim 1, wherein
Q is represented by the following formula:
Figure USRE038188-20030715-C00395
R is 5-methyl-2-phenyl;
A is represented by the following formula:
Figure USRE038188-20030715-C00396
and
B is represented by the following formula:
Figure USRE038188-20030715-C00397
32. Ethylene derivatives as claimed in claim 1, wherein
Q is represented by the following formula:
Figure USRE038188-20030715-C00398
R is 5-ethyl-2-phenyl;
A is represented by the following formula:
Figure USRE038188-20030715-C00399
and
B is represented by the following formula:
Figure USRE038188-20030715-C00400
33. Ethylene derivatives as claimed in claim 1, wherein
Q is represented by the following formula:
Figure USRE038188-20030715-C00401
R is 5-isopropyl-2-phenyl;
A is represented by the following formula:
Figure USRE038188-20030715-C00402
and
B is represented by the following formula:
Figure USRE038188-20030715-C00403
34. An agricultural chemical comprising, as an active ingredient, one or more ethylene derivatives of claim 1.
35. An insecticidal or acarcicidal agent comprising, as an active ingredient, one or more ethylene derivatives of claim 1.
36. An agent for preventing the attachment of aquatic organisms to a substrate, the agent comprising, as an active ingredient, one or more ethylene derivatives of claim 1.
37. A method for controlling insects, acari, nematodes, herbs or fungi, comprising applying an agricultural chemical comprising, as an active ingredient, one or more compounds of claim 1.
38. A method for controlling insects or acari comprising applying an insecticidal or acarcicidal agent comprising, as an active ingredient, one or more compounds of claim 1.
39. A method for preventing the attachment of aquatic organisms to a substrate, comprising applying to said substrate an agent comprising, as an active ingredient, one or more compounds of claim 1.
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