KR900001657A - 피라졸 유도체 및 그를 함유하는 제초제 - Google Patents
피라졸 유도체 및 그를 함유하는 제초제 Download PDFInfo
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- KR900001657A KR900001657A KR1019890010068A KR890010068A KR900001657A KR 900001657 A KR900001657 A KR 900001657A KR 1019890010068 A KR1019890010068 A KR 1019890010068A KR 890010068 A KR890010068 A KR 890010068A KR 900001657 A KR900001657 A KR 900001657A
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- South Korea
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- same
- alkyl group
- alkyl
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- 150000003217 pyrazoles Chemical class 0.000 title claims abstract 6
- 239000004009 herbicide Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 3
- 239000011593 sulfur Substances 0.000 claims abstract 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 15
- 229910004013 NO 2 Inorganic materials 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 4
- -1 cyanomethyl group Chemical group 0.000 claims 4
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 2
- 101150065749 Churc1 gene Proteins 0.000 claims 2
- 102100038239 Protein Churchill Human genes 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000004997 halocarbonyl group Chemical group 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 150000002367 halogens Chemical group 0.000 abstract 6
- 150000002431 hydrogen Chemical group 0.000 abstract 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 abstract 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
Classifications
-
- 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
-
- 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/24—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms having sulfone or sulfonic acid radicals in the molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/65031—Five-membered rings having the nitrogen atoms in the positions 1 and 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- 하기일반식(I)의 피라졸 유도체 및 그의 염.[식중, A는 C1~C4알킬기, C2~C4알케닐기 또는 C2~C4알키닐기이며 ; B는 수소원자, C1~C3알킬기, 할로겐원자, C1~C3할로알킬기, C1~C3알콕시기, C1~C3알킬티오기, C2~C4알콕시 알킬기, C2~C4알킬티오알킬기 또는 C2~C4알콕시카르보닐기이며 ; X는 C1~C6알킬기, C1~C6알콕시기, 할로겐원자, 니트로기, 시아노기, C1~C6할로알킬기, C2~C6알콕시알킬기, C2~C6알킬카르보닐기, C2~C6알콕시카르보닐기, 수소원자 또는 C1~C6알킬기에 의해 각각 치환된 아미노카르보닐기, C1~C6할로알콕시기, C1~C6알킬티오기 또는 C2~C6알킬티오알킬기이며; Y는 -OR1(식중, R1은 C3~C8시클로알킬기, C4~C8시클로알킬알킬기, C3~C6알케닐기, C2~C6알키닐기, C1~C6할로알킬기, C3~C8할로시클로알킬알킬기, C3~C6할로알케닐기, C2~C6할로알키닐기, C2~C6니트로알킬기 또는 C1~C3알킬기, 할로겐원자, 니트로기 또는 C1~C3알콕시기에 의해 치환될 수 있는 페닐기이다.) -O-L-O-R1(식중, L은 C1~C3알킬기에 의해 치환될 수 있는 C1~C6알킬렌기이고, R1은 상기와 동일하다.), -O-L-OH(식중, L은 상기와 동일하다.), -O-L-O-L-O-R2(식중, L은 상기와 동일하고, R2는 수소원자, C1~C6알킬기 또는 C1~C3알킬기, 할로겐원자, 니트로기 또는 C1~C3알콕시기에 의해 치환될 수 있는 페닐기이다.), -O-L-R3(식중, L은 상기와 동일하고, R3는 C1~C3알킬기, 할로겐원자, 니트로기 또는 C1~C3알콕시기에 의해 치환될 수 있는 페닐기이다.), -O-M(식중, M은 2개 이하의 황 또는 산소원자를 함유하며, 1 내지 4개의 탄소원자의 결합에 의해 형성된 3 내지 6원소의 지방족고리기이다)., -O-L-M(식중, L 및 M은 상기와 동일하다.), O-L-NR4R5(식중, L은 상기와 동일하고, 동일 또는 상이할 수 있는 R4및 R5의 각각은 수소원자 또는 C1~C6알킬기이거나, 또는 R4및 R5는 인접한 질소원자와 함께 고리를 형성한다.), -O-L-COOR4(식중, L 및 R4는 상기와 동일하다.), -O-CH=CH-COOR4(식중 R4는 상기와 동일하다.), -O-L-CN(식중, L은 상기와 동일하다.), -O-L-C(O)-R2(식중, L 및 R2는 상기와 동일하다.), -O-L-S(O)n-R4(식중, L 및 R4는 상기와 동일하고, n은 0 내지 2의 정수이다.), -O-COOR4(식중, R4는 상기와 동일하다.), O-CONR4R6(식중, R4및 R5는 상기와 동일하다.), -OP(O)(OR4)2(식중, R4는 상기와 동일하다.), -S(O)nR1(식중, R1및 n은 상기와 동일하다.), 또는 -S(O)n-L-O-R1(식중, L,R1및 n은 상기와 동일하다.)이며 ; Z는 할로겐원자, 니트로기, C1~C3알콕시기, 트리플루오로메틸기, 트리플루오로메톡시기, 시아노기 또는 -S(O)nR6(식중, n은 상기와 동일하고, R6는 C1~C3알킬기 또는 C1~C3할로알칼기이다.)이며 ; V는 수소원자, 할로겐원자, C1~C4알킬기 또는 C1~C4알콕시기이며 ; W는 수소원자, 할로겐원자, C1~C4알킬기, C1~C4할로알킬기, C1~C4알콕시기, C2~C6알콕시알킬기, C2~C5알콕시카르보닐기, C1~C3할로알콕시기, 니트로기, 시아노기 또는 -S(O)nR6(식중, n및 R6은 상기와 동일하다.)이고 ; Q는 수소원자, 할로겐원자에 의해 치환될 수 있는 C1~C6알킬기, 할로겐원자에 의해 치환될 수 있는 C1~C6알케닐기, 할로겐원자에 의해 치환될 수 있는 C1~C6알키닐기, 시아노메틸기, C(O)-R7(식중, R6은 C1~C6알킬기, C1~C6알케닐기, C1~C6알키닐기, C1~C6할로알킬기, C1~C6할로알케닐기, C1~C6할로알키닐기, 할로겐원자, 니트로기 및 트리플루오로메틸기를 포함하는 군으로부터 선택한 동일 또는 상이한 치환체에 의해 치환될 수 있는 페닐기, C1~C6알킬기, C1~C6알콕시기 또는 히드록실기이다.), -S(O)2R7(식중, R7은 상기와 동일하다.), -P(O)(OR7)2(식중, R7은 상기와 동일하다.), -L-C(O)-R7(식중, L 및 R7는 상기와 동일하다.), -L-C(O)-N(R8)(R9)(식중, L은 상기와 동일하고, 동일 또는 상이할 수 있는 R8및 R9의 각각은 수소원자 또는 C1~C6알킬기이다.), -L-R10(식중, L은 상기와 동일하고, R10은 할로겐원자, 니트로기 및 트리플루오로메틸기를 포함하는 군으로부터 선택한 동일 또는 상이한 치환체에 의해 치환될 수 있는 페닐기, C1~C6알킬기, C1~C6알콕시기 또는 히드록실기이다.), -L-N(R8)(R9)(식중, L,R8및 R9는 상기와 동일하다.), -L-OR11(식중, L은 상기와 동일하고, R11은 수소원자, C1~C6알킬기 또는 C1~C6알케닐기이다.), -L-OC(O)R11(식중, L은 상기와 동일하고, R12는 C1~C6알킬기 또는 C1~C6알콕시기이다.), -L-S(O)nR11(식중, L,n 및 R11은 상기와 동일하다.), -L-SC(O)R8(식중, L 및 R8은 상기와 동일하다.),(식중, 동일 또는 상이할 수 있는 L1 및 L2의 각각은 메틸렌기, 산소원자 또는 황원자이며, R12는 수소원자 또는 C1~C3알킬기이고, m은 2 또는 3이다.)이다.]
- 제1항에 있어서, A,B,X,Y,Z 및 O가 A : Me,Et,n-Pr,i-Pr, CH2CH=CH2,CH2C CH,t-BuB : H,Me,Et,n-Pr,i-Pr,Cl,Br,CH2Cl,CF3,OMe,OEt,OPr-i,SMe,CH2OMe,CH2SMe, CO2Me,CO2EtX : Me,Et,n-Pr,i-Pr,n-Bu,i-Bu,s-Bu,t-Bu,OMe,OEt,OPr-n,OPr-i,OBu-n, OBu-i,OBu-s,OBu-t,F,Cl,Br,I,NO2,CN,CH2F,CHF2,CF3,CH2CF3, CH2Cl,CCl3, CHCIMe, CH2CH2Cl,CHClCH2Cl,CH2Br,CHBrMe,CH2CH2Br,CH2OMe,CH2OEt,CH2OPr-n,CH2OPr-i, CH2OBu-i,CH2u-s,CH2OBu-t,CHMeOMe,CHMeOEt,OHMeOPr-n,CHMeOPr-i,CHMeOBu-n,CHMeOBu-i, CHMeOBu-s,CHMeOBu-t,CH2CH2OMe,CH2CH2OEt,CH2CH2OPr-i,Ac,COEt,COPr-n,COPr-i, COOMe,COOEt,COOPr-i,CONHMe,CONHEt,CONMe2,CONET2,CONEtMe,OCHF2,OCF3,OCH2CF3, SMe, SEt,CH2SMe,CH2SEt,CHMeSMe,CHMeSEtOCHMeCH=CH2,OCMe2CH=CH2,OCH2CMe=CH2,OCH2CH=CHMe,OCH2CH=CMe2,OCH2C CH,OCHMeC CH, OCMe2C CH,OCH2C CMe,OCH2CH2F,OCH2CHF2,OCH2CF3,OCH2CH2Cl,OCHM eCH2Cl,OCH2CCl3, OCH2CH2CH2Cl, OCH2CH2BrOCH2CCl=C2,OCH2CH2CH=CH2,OCH2CCl=CHCl,OCH2CH2NO2, OPh,OPh-Me-2OPh-Cl-4, OPh-NO2-4,OCH2CH2OMe,OCH2CH2OEt,OCH2CH2OPr-N,OCH2CH2OPr-i,OCH2CH2OBu-n,OCH2CH2OBu-i,OCH2CH2Bu-s,OCH2CH2OBu-t,OCHMeCH2OMe,OHC2CH2OPh, OCH2CH2OCH2CH2OMe,OCH2CH2OH,OCH2CH2OCHMe CH2OMe,OCH2Ph,OCHMePh,OCH2Ph-4-ME,OCH2Ph-4-Cl,OCH2CH2Ph,OCH2CH2NH2,OCH2CH2NHMe,OCH2CH2NMe2,OCH2CH2NEt2,,OCH2,COOMe,OCH2COOEt,OCH2COOPrn,OCH2COOPri,OCH2COOBut,OCHMeCOOMe,OCHMeCOOEtOCHMeCOOPrn,OCHMeCOOPr-i,OCHMeCOOBut,OCH2CH2CN,OCH2CN,OCHMeCN,OCH2SMe,OCH2C(O)Ph,OCH2C(O)Me,OCH2CH2SMe,OCH2CH2SOMe,OCH2CH2SO2Me,OCH2CH2SEt,OCH2SO2Et,OCOOMe,OCOOEt,OCOOPri,OCONH2,OCONHMe,OCONMe2,OP(O)(OMe)2,OP(O)(OEt)2,SCH2CH=CH2,SCH2C CH,SCH2CF3, SCH2CH2Cl,SCH2CCl,SPh, SCH2CH2OMe, SCH2CH2OEt, SCH2CH2OPr-i, SCH2CH2OPh,S(O)CH2CH=CH2,S(O)CH2CHCH,S(O)CH2CF3,S(O)CH2CH2Cl,S(O)Ph, S(O)CH2CH2OMe,S(O)CH2CH2OEt,S(O)CH2CH2OPr-i, S(O)CH2CH2OPh,SO2CH2CH=CH2SO2CH2CCH, SO2CH2CF3,SO2CH2CHSO2CH2CH2OMe, SO2CH2CH2OEt, SO2CH2CH2OPr-i, Z: F,Cl,Br,I ,NO2,OMe,OEt, OPr-n,OPr-i,CH3,CN,SMe,SOMe,SO2Me,SCF3,SOCF3,SO2CF3 Q: H, Me,Et, N-Pr,i-Pr, n-Bu,i-Bu,s-Bu,t-Bu,CH2CH2Cl, CH2CF3, CHClMe, CH2CH2Br, CHClCH2Cl, CH2CH=CH2, CH2CMe=CH2,CH2CH=CHMe,CH2C CH,CH2CCl=CH2,CH2CN,CH2Ph,CH2Ph-Cl-2, CH2Ph-Cl-3, CH2Ph-Me-2,CH2Ph-Me2-2,4,CH2Ph-Me-4,CHMePh, CHEtPh, CH2Ph-NO2-2,CH2Ph-CF3-3,CH2OMe, CH2OEt, CH2OH,CHMeOH, CH2NHMe,CH2NMe2, CHMeNMe2,CH2COPh, CH2COPh-NO2-4,CH2COPh-Me-4,CH2COPh-Cl-4,CH2COPh-ME2-2,4, CH2COPh-CF3-4,CH2Ac,CH2COEt,CHMeAc,CH2CO2Me,CH2CO2Et,CH2CO2Pr-n,CH2CO2Pr-i, CH2CO2Bu-t,CH2CO2H,CHMeCO2H,CH2CONHMe,CH2CONMe2,CH2CONHEt,CH2CONEt2,CH2CONPr-n2, CH2OCH2CH=CH2,CH2,CH2OAc,CH2COEt,CH2COPr-i,CH2COBu-t,CH2OCO2Me,CH2OCO2Et,CH2OCO2Pr-i, CH2OCO2Bu-t,CH2SMe,CH2SEt,CH2SCH2CH=CH2,CH2SAc,CH2SCOBu-t,CH2SO2Me, CH2SO2Et, CH2SO2CH2CH=CH2,CH2NHCH2CH=CH2,CH2NMeCH2CH=CH2,CH2NHAc,CH2NHCOEt,CH2NHCO2Me, CH2NHCO2Et, CH2NHCO2Me,CH2NHCO2Et, CH2NMeCO2Me,COPh,COPh-Me-4,COPh-NO2-2,COPh-Cl2-2, 4, Ac, COEt,COPr-n,COPr-i,COBu-n,COBu-t,COCH2Cl,COCHCL2,COCCl3,COCF3, COCH2OMe, COCH2OPh,COCH2CH=CHCH3,CO2Me,CO2Et,CO2Bu-t,CO2Pr-i,CONHMe,CONMe2,CONHEt, CONEt2, CONPr-n2,CON(CH2CH=CH2)2,CONMePh,CO2CH2Ph,CO2Ph,SO2Me,SO2Et,SO2CH2CH=CH2,SO2Ph,SO2Ph-Me-4,SO2Ph-Cl-4,SO2Ph-(NO2)2-2,4,SO2CF3,P(=0)(OMe)2,P(O)(OEt)2,P(=O)(OPr-n)2,P(=O)(OPr-i)2,P(=S)(OMe)2,P(=S) (OEt)2,P(=O)OMeOPh,P(=O)(OCH2CH=CH2)2,P(=O)OPhOCH2CH=CH2; 임을 특징으로 하는 일반식(I)의 피라졸 유도체 및 그의 염.
- 제1항에 기재된 일반식(I)의 피라졸 유도체 또는 그의 염의 제초 유효량 및 농업용 담체 또는 희석제를 함유함을 특징으로 하는 선택성 제초 조성물.
- 제1항에 기재된 일반식(I)의 피라졸 유도체 또는 그의 염의 제초 유효량을 방제하려는 구역에 산포함을 특징으로 하는 잡초 방제방법.
- 하기일반식(II)의 치환된 벤젠 유도체 및 그의 염[식중, G는 카르복실기, 할로카르보닐기 또는 시아노카르보닐기이며 ; X는 C1~C6알킬기, C1~C6알콕시기, 할로겐원자, 니트로기, 시아노기, C1~C6할로알킬기, C2~C6알콕시알킬기, C2~C6알킬카르보닐기, C2~C6알콕시카르보닐기, 수소원자 또는 C1~C6알킬기에 의해 각각 치환된 아미노카르보닐기, C1~C6할로알콕시기, C1~C6알킬티오기 또는 C2~C6알킬티오 알킬기이며 ; Y는 -OR1(식중, R1은 C3~C8시클로알킬기, C4~C8시클로알킬알킬기, C3~C6알케닐기, C2~C6알키닐기, C1~C6할로알킬기, C3~C8할로시클로알킬알킬기, C3~C6할로알케닐기, C2~C6할로알키닐기, C2~C6니트로알킬기 또는 C1~C3알킬기, 할로겐원자, 니토로기 또는 C1~C3알콕시기에 의해 치환될 수 있는 페닐기이다.), -O-L-O-R1(식중, L은 C1~C3알킬기에 의해 치환될 수 있는 C1~C6알킬렌기이고, R1은 상기와 동일하다.), -O-L-OH(식중, L은 상기와 동일하다.), -O-L-O-L-O-R2(식중, L은 상기와 동일하고, R2는 수소원자, C1~C6알킬기 또는 C1~C3알킬기, 할로겐원자, 니트로기 또는 C1~C3알콕시기에 의해 치환될 수 있는 페닐기이다.), -O-L-R3(식중, L은 상기와 동일하고, R3는 C1~C3알킬기, 할로겐원자, 니트로기 또는 C1~C3알콕시기에 의해 치환될 수 있는 페닐기이다.),-O-M(식중, M은 2개이하의 황 또는 산소원자를 함유하며, 1 내지 4개의 탄소원자의 결합에 의해 형성된 3 내지 6원소의 지방족 고리기이다.), -O-L-M(식중, L 및 M은 상기와 동일하다.), O-L-NR4NR5(식중, L은 상기와 동일하고, 동일 또는 상이할 수 있는 R4및 R5의 각각의 수소원자 또는 C1~C6알킬기이거나, 또는 R4및 R5는 인접한 질소원자와 함께 고리를 형성한다.), -O-L-COOR4(식중, L 및 R4는 상기와 동일하다.), -O-CH=CH-COOR4(식중, R4는 상기와 동일하다.), -O-L-CN(식중, L은 상기와 동일하다.), -O-L-C(O)-R2(식중, L 및 R2는 상기와 동일하다.), -O-L-S(O)n-R4(식중, L 및 R4는 상기와 동일하고, n은 0 내지 2의 정수이다.), -O-COOR4(식중, R4는 상기와 동일하다.), O-CONR4R6(식중, R4및 R5는 상기와 동일하다.), -OP(O)(OR4)2(식중, R4는 상기와 동일하다.), -S(O)nR1(식중, R1및 n은 상기와 동일하다.), 또는 -S(O)n-L-O-R1(식중, L,R1및 n은 상기와 동일하다.)이며 ; Z는 할로겐원자, 니트로기, C1~C3알콕시기, 트리플루오로메틸기, 트리플루오로메톡시기, 시아노기 또는 -S(O)nR6(식중, n은 상기와 동일하고, R6는 C1~C3알킬기 또는 C1~C3할로알칼기이다.)이며 ; V는 수소원자, 할로겐원자, C1~C4알킬기 또는 C1~C4알콕시기이며 W는 수소원자, 할로겐원자, C1~C4알킬기, C1~C4할로알킬기, C1~C4알콕시기, C2~C6알콕시알킬기, C2~C5알콕시카르보닐기, C1~C3할로알콕시기, 니트로기, 시아노기 또는 -S(O)nR6(식중, n및 R6은 상기와 동일하다.)이다.]※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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Family
ID=26363753
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019890010068A KR0128286B1 (ko) | 1988-07-15 | 1989-07-14 | 피라졸 유도체 및 그를 함유하는 제초제 |
Country Status (13)
Country | Link |
---|---|
US (2) | US4986845A (ko) |
EP (1) | EP0352543B1 (ko) |
KR (1) | KR0128286B1 (ko) |
CN (1) | CN1017240B (ko) |
AT (1) | ATE112271T1 (ko) |
BR (1) | BR8903486A (ko) |
CA (1) | CA1338788C (ko) |
DE (1) | DE68918524T2 (ko) |
DK (1) | DK170439B1 (ko) |
ES (1) | ES2064388T3 (ko) |
HU (1) | HU205912B (ko) |
IL (1) | IL90819A (ko) |
RU (2) | RU1792280C (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100643510B1 (ko) * | 2005-01-20 | 2006-11-10 | 박현문 | 반도체 장비용 대형 오링의 제조장치 및 그 성형장치에의해 제조된 대형 오링 |
Families Citing this family (53)
Publication number | Priority date | Publication date | Assignee | Title |
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DE4008403A1 (de) * | 1990-03-16 | 1991-09-19 | Merck Patent Gmbh | Glykolsaeurederivate |
ES2134257T3 (es) * | 1992-03-03 | 1999-10-01 | Idemitsu Kosan Co | Derivado de pirazol. |
DE4311722C1 (de) * | 1993-04-08 | 1994-04-07 | Basf Ag | Verfahren zur Herstellung von Halogenmethyl-benzoylcyaniden und neue Halogenmethyl-benzoylcyanide |
CA2175675A1 (en) * | 1993-11-09 | 1995-05-18 | Mitsuru Shibata | Pyrazole derivatives and herbicide containing the same |
JP3478412B2 (ja) * | 1994-01-27 | 2003-12-15 | 富士写真フイルム株式会社 | ピラゾール化合物 |
BR9509751A (pt) * | 1994-11-24 | 1998-06-16 | Basf Ag | Processo para preparar cianetos de halometilbenzoíla |
ATE239018T1 (de) * | 1995-02-13 | 2003-05-15 | Idemitsu Kosan Co | Pyrazol-derivate |
CA2210693C (en) | 1995-02-24 | 2008-04-22 | Basf Aktiengesellschaft | Pyrazol-4-yl-benzoyl derivatives and their use as herbicides |
DE19532312A1 (de) * | 1995-09-01 | 1997-03-06 | Basf Ag | Pyrazol-4-yl-benzoylderivate |
CA2278331C (en) * | 1997-01-17 | 2008-11-18 | Basf Aktiengesellschaft | 3-heterocyclyl-substituted benzoyl derivatives |
AR012141A1 (es) * | 1997-03-24 | 2000-09-27 | Dow Agrosciences Llc | PROCESO PARA PREPARAR 1-ALQUILO-4-(2-CLORO-3-ALCOXIBENCENO), COMPUESTOS INTERMEDIARIOS DE APLICACIoN EN DICHO PROCESO Y PROCEDIMIENTO PARA PREPARAR DICHOS COMPUESTOS INTERMEDIARIOS |
US6211403B1 (en) | 1997-03-24 | 2001-04-03 | Dow Agrosciences Llc | Process for preparing 2-chloro-3-alkoxy-4-alkylsulfonyl-benzoic acids and esters |
AR012142A1 (es) | 1997-03-24 | 2000-09-27 | Dow Agrosciences Llc | Compuestos de 1-alquil-4-benzoil-5-hiroxipirazol, composiciones herbicidas que los contienen; metodo para controlar vegetacion no deseada y compuestosintermediarios utiles para preparar dichos compuestos |
CA2289003A1 (en) * | 1997-05-07 | 1998-11-12 | Basf Aktiengesellschaft | Substituted 4-benzoyl-pyrazoles |
AU731305B2 (en) * | 1997-05-23 | 2001-03-29 | Dow Agrosciences Llc | 1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their use as herbicides |
EP1077972A1 (en) * | 1998-05-22 | 2001-02-28 | Dow AgroSciences LLC | 1-alkyl-4-[(3-oxetanyl-)benzoyl]-5-hydroxypyrazole compounds and their use as herbicides |
WO2000003988A1 (fr) * | 1998-07-14 | 2000-01-27 | Nippon Soda Co., Ltd. | Nouveaux derives de l'acide benzoique et procedes de preparation associes |
PL348888A1 (en) | 1998-12-04 | 2002-06-17 | Basf Ag | 3-(heterocyclyl)-substituted benzoylpyrazols |
DE19914140A1 (de) | 1999-03-27 | 2000-09-28 | Bayer Ag | Substituierte Benzoylpyrazole |
DE19946853A1 (de) * | 1999-09-30 | 2001-04-05 | Bayer Ag | Substituierte Arylketone |
RU2299879C2 (ru) * | 2000-01-17 | 2007-05-27 | Байер Акциенгезелльшафт | Замещенные арилкетоны |
DE10037149A1 (de) * | 2000-07-29 | 2002-02-07 | Bayer Ag | Substituierte Arylketone |
DE10043074A1 (de) * | 2000-09-01 | 2002-03-14 | Aventis Cropscience Gmbh | Herbizid wirksame Benzoylcyclohexandione |
DE10136449A1 (de) * | 2001-05-09 | 2002-11-14 | Bayer Ag | Substituierte Arylketone |
BR0209537A (pt) * | 2001-05-09 | 2004-03-09 | Bayer Cropscience Ag | Arilcetonas substituìdas |
DE10138577A1 (de) * | 2001-05-21 | 2002-11-28 | Bayer Ag | Substituierte Benzoylpyrazole |
DE10206792A1 (de) * | 2002-02-19 | 2003-08-28 | Bayer Cropscience Ag | Substituierte Arylketone |
DE10209645A1 (de) * | 2002-03-05 | 2003-09-18 | Bayer Cropscience Ag | Substituierte Arylketone |
DE10235945A1 (de) * | 2002-08-06 | 2004-02-19 | Bayer Cropscience Gmbh | 3-Aminocarbonyl substituierte Benzoylpyrazolone |
WO2005058037A1 (en) * | 2003-12-12 | 2005-06-30 | Syngenta Participations Ag | Picolinylpyrazoles as herbicides |
AR056889A1 (es) * | 2005-12-15 | 2007-10-31 | Ishihara Sangyo Kaisha | Compuestos benzoilpirazol y herbicidas que los contienen |
UA94003C2 (uk) | 2006-11-28 | 2011-03-25 | Ишихара Санджай Кайша, Лтд. | Сполуки бензоїлпіразолу, гербіцид на їх основі та спосіб боротьби з небажаними рослинами |
JP5420169B2 (ja) * | 2006-12-27 | 2014-02-19 | 石原産業株式会社 | ベンゾイルピラゾール系化合物を含有する除草剤 |
JP5416354B2 (ja) * | 2007-02-02 | 2014-02-12 | 石原産業株式会社 | ベンゾイルピラゾール系化合物を含有する除草性組成物 |
EP1980556A1 (de) | 2007-04-12 | 2008-10-15 | Bayer CropScience AG | 4-(4-Trifluormethyl-3-thiobenzoyl)pyrazole und ihre Verwendung als Herbizide |
DE102007026875A1 (de) | 2007-06-11 | 2008-12-24 | Bayer Cropscience Ag | 3-Cyclopropyl-4-(3-thiobenzoyl)pyrazole und ihre Verwendung als Herbizide |
JP5449855B2 (ja) * | 2008-05-20 | 2014-03-19 | 石原産業株式会社 | ピラゾール系化合物、それらの製造方法及びそれらを含有する除草剤 |
EP2127521A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience Aktiengesellschaft | Herbizid wirksame 4-(3-Alkylsulfinylbenzoyl)pyrazole |
JP5584452B2 (ja) | 2008-12-11 | 2014-09-03 | 石原産業株式会社 | ベンゾイルピラゾール系化合物を含有する除草性組成物 |
JP5795314B2 (ja) * | 2009-07-29 | 2015-10-14 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 4−(3−アルキルチオベンゾイル)ピラゾール類及び除草剤としてのそれらの使用 |
BR112012023761A2 (pt) | 2010-03-23 | 2015-10-06 | Basf Se | piridina substituída de fórmula i, composto de fórmula i, composição e método para controle de vegetação indesejada |
WO2011117211A1 (en) | 2010-03-23 | 2011-09-29 | Basf Se | Substituted pyridazines having herbicidal action |
JP2013522339A (ja) | 2010-03-23 | 2013-06-13 | ビーエーエスエフ ソシエタス・ヨーロピア | 除草作用を有する置換されたピリジン |
WO2011117210A1 (en) | 2010-03-23 | 2011-09-29 | Basf Se | Substituted pyridines having herbicidal action |
EP2550279A1 (en) | 2010-03-23 | 2013-01-30 | Basf Se | Pyrazinothiazines having herbicidal action |
AR081526A1 (es) | 2010-03-23 | 2012-10-03 | Basf Se | Piridazinas sustituidas que tienen accion herbicida |
CN103003247B (zh) | 2010-07-21 | 2015-06-10 | 拜耳知识产权有限责任公司 | 4-(4-卤代烷基-3-硫代苯甲酰基)吡唑及其作为除草剂的用途 |
MX2013005694A (es) | 2010-12-23 | 2013-07-05 | Basf Se | Piridinas sustituidas que tienen accion herbicida. |
WO2012168241A1 (en) | 2011-06-09 | 2012-12-13 | Basf Se | Substituted pyrazines having herbicidal activity |
AR086894A1 (es) | 2011-06-09 | 2014-01-29 | Basf Se | Derivados de 2,2-dioxo-oxatiin[3,2-b]piridina, una composicion que los comprende y un metodo para controlar vegetacion indeseada que los emplea |
JP2015523340A (ja) | 2012-06-01 | 2015-08-13 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 除草活性を有する置換ピリジン化合物 |
US20160102103A1 (en) | 2013-05-24 | 2016-04-14 | Basf Se | Substituted pyridine compounds having herbicidal activity |
CN108264484A (zh) * | 2016-12-30 | 2018-07-10 | 浙江省化工研究院有限公司 | 一种带醚结构的取代的苯基酮类化合物、其制备方法及应用 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5436648B2 (ko) * | 1974-03-28 | 1979-11-10 | ||
FR2277826A2 (fr) * | 1974-07-09 | 1976-02-06 | Sandoz Sa | Stabilisation de matieres organiques au moyen de derives de pyrazole |
US4083925A (en) * | 1976-03-22 | 1978-04-11 | Martin Marietta Aluminum, Inc. | Method for removing ferrous iron from alkali metal aluminate liquor |
US4230481A (en) * | 1977-08-12 | 1980-10-28 | Ishihara Sangyo Kaisha Limited | Pyrazole derivatives useful as a herbicidal component |
JPS58185568A (ja) * | 1982-04-24 | 1983-10-29 | Nissan Chem Ind Ltd | ピラゾ−ル誘導体,その製造方法および該誘導体を含有する選択性除草剤 |
US4744815A (en) * | 1985-05-11 | 1988-05-17 | Nissan Chemical Industries, Ltd. | 4-benzoyl-1-alkyl (alkenyl) - pyrazoles, composition containing them, herbicidal method of using them, and intermediate in their preparation |
US4643757A (en) * | 1985-05-20 | 1987-02-17 | Nissan Chemical Industries, Ltd. | Herbicidal 4-benzoyl-1-methyl-5-hydroxypyrazoles |
IL85659A (en) * | 1987-03-17 | 1992-03-29 | Nissan Chemical Ind Ltd | 4-benzoylpyrazole derivatives,method for their preparation and herbicidal compositions containing them |
-
1989
- 1989-06-21 US US07/369,523 patent/US4986845A/en not_active Ceased
- 1989-06-29 CN CN89104508A patent/CN1017240B/zh not_active Expired
- 1989-06-30 IL IL9081989A patent/IL90819A/en not_active IP Right Cessation
- 1989-06-30 CA CA000604603A patent/CA1338788C/en not_active Expired - Fee Related
- 1989-07-11 EP EP89112691A patent/EP0352543B1/en not_active Expired - Lifetime
- 1989-07-11 AT AT89112691T patent/ATE112271T1/de not_active IP Right Cessation
- 1989-07-11 ES ES89112691T patent/ES2064388T3/es not_active Expired - Lifetime
- 1989-07-11 DE DE68918524T patent/DE68918524T2/de not_active Expired - Fee Related
- 1989-07-14 KR KR1019890010068A patent/KR0128286B1/ko not_active IP Right Cessation
- 1989-07-14 DK DK349289A patent/DK170439B1/da not_active IP Right Cessation
- 1989-07-14 RU SU4614419A patent/RU1792280C/ru active
- 1989-07-14 HU HU893573A patent/HU205912B/hu not_active IP Right Cessation
- 1989-07-14 BR BR898903486A patent/BR8903486A/pt not_active Application Discontinuation
-
1991
- 1991-12-03 RU SU915010216A patent/RU2042667C1/ru not_active IP Right Cessation
-
1992
- 1992-09-18 US US07/946,900 patent/USRE34779E/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100643510B1 (ko) * | 2005-01-20 | 2006-11-10 | 박현문 | 반도체 장비용 대형 오링의 제조장치 및 그 성형장치에의해 제조된 대형 오링 |
Also Published As
Publication number | Publication date |
---|---|
ES2064388T3 (es) | 1995-02-01 |
DK349289A (da) | 1990-01-16 |
IL90819A (en) | 1994-06-24 |
HUT51256A (en) | 1990-04-28 |
US4986845A (en) | 1991-01-22 |
BR8903486A (pt) | 1990-03-13 |
HU205912B (en) | 1992-07-28 |
AU618609B2 (en) | 1992-01-02 |
DK349289D0 (da) | 1989-07-14 |
ATE112271T1 (de) | 1994-10-15 |
DE68918524T2 (de) | 1995-05-04 |
CN1039586A (zh) | 1990-02-14 |
RU1792280C (ru) | 1993-01-30 |
EP0352543A1 (en) | 1990-01-31 |
IL90819A0 (en) | 1990-01-18 |
DE68918524D1 (de) | 1994-11-03 |
EP0352543B1 (en) | 1994-09-28 |
CA1338788C (en) | 1996-12-10 |
RU2042667C1 (ru) | 1995-08-27 |
AU3800589A (en) | 1990-01-25 |
USRE34779E (en) | 1994-11-08 |
DK170439B1 (da) | 1995-09-04 |
KR0128286B1 (ko) | 1998-04-02 |
CN1017240B (zh) | 1992-07-01 |
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