KR870006006A - 1-아릴-피라졸의 제조 방법 - Google Patents
1-아릴-피라졸의 제조 방법 Download PDFInfo
- Publication number
- KR870006006A KR870006006A KR860011007A KR860011007A KR870006006A KR 870006006 A KR870006006 A KR 870006006A KR 860011007 A KR860011007 A KR 860011007A KR 860011007 A KR860011007 A KR 860011007A KR 870006006 A KR870006006 A KR 870006006A
- Authority
- KR
- South Korea
- Prior art keywords
- carbon atoms
- straight
- aryl
- nitro
- cyano
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 3
- 125000004961 1-arylpyrazolyl group Chemical group 0.000 title claims 2
- -1 alkali metal azide Chemical class 0.000 claims 32
- 125000004432 carbon atom Chemical group C* 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims 2
- 125000006000 trichloroethyl group Chemical group 0.000 claims 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000005493 Chloridazon (aka pyrazone) Substances 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000005998 bromoethyl group Chemical group 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 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
- C07D231/38—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- (a-1) : 일반식(II)의 5-할로겐-1-아릴-피라졸을, 경우에 따라 희석제의 존재하에 일반식(III)의 알칼리금속 아지드와 반응시키거나; (a-2) : 일반식(IV)의 5-하이드라지노-1-아릴-피라졸을, 촉매산의 존재하 및 경우에 따라, 희석제의 존재하에, 일반식(V)의 알칼리금속 아질산염과 디아조화시키거나; (b) : 방법 (a-1) 또는 (a-2)에 의해 수득 가능한, 일반식(Ia)의 5-아지도-1-아릴-피라졸을 경우에 따라 희석제의 존재하에, 일반식(VI)의 포스핀 또는 포스파이트와 2단계로 반응시킴을 특징으로 하여, 일반식(I)의 1-아릴-피라존을 제조하는 방법.상기식에서, R은 시아노 또는 니트로를 나타내고, Ar은 각각 임의로 치환된 페닐 또는 피리딜을 나타내며, X는 아지도 그룹을 나타내거나, 라디칼를 나타내고, R1,R2및 R3는 서로 독립적으로 각각 알킬, 알케닐, 알키닐, 할로게노알킬, 알콕시, 알콕시알킬, 사이클로알킬 또는 사이클로알킬옥시를 나타내거나, 각각 임의로 치환된 아릴, 아릴옥시, 아르알킬 또는 아르알킬옥시를 나타내는데, 단, R이 시아노를 나타냄과 동시에 X가 아지도그룹을 나타내는 경우, Ar은 비치환된 페닐은 나타내지않고 또한 5-니트로-2-피리딜을 나타내지 않으며, Hal은 할로겐을 나타내며, M+은 알칼리금속 양이온을 나타낸다.
- 제1항에 있어서, 기의 정의가 하기와 같은 일반식(I)이 1-아릴-피라졸을 제조하는 방법.R은 시아노 또는 니트로를 나타내고, Ar은 각각 시아노, 니트로, 할로겐탄소수 1 내지 4의 직쇄 또는 측쇄 알킬, 탄소수 1 내지 4의 직쇄 또는 측쇄 알콕시 또는 탄소수 1 내지 4의 직쇄 또는 측쇄 알콕시카보닐, 탄소원자 1 내지 4개를 가지며 같거나 다른 할로겐원자 1 내지 9개를 갖는 직쇄 또는 측쇄 할로겐알킬, 탄소원자 1 내지 4개를 가지며 같거나 다른 할로겐원자 1 내지 9개를 갖는 직쇄 또는 측쇄 할로겐알콕시 및 라디칼 -S(O)n-R4중에서 선택된 같거나 다른 치환체에 의해 임의로 일치환되거나 다-치환된 페닐, 2-피리딜, 3-피리딜 또는4-피리딜을 나타내고, X는 아지도 그룹을 나타내거나 라디칼을 나타내고 R1,R2및 R3는 서로 독립적으로, 각각 탄소수 8이하의 직쇄 또는 측쇄 알킬, 알케닐 또는 알키닐을 나타내거나, 탄소원자 1 내지 6개를 가지며 같거나 다른 할로겐원자 1 내지 13개를 갖는 직쇄 또는 측쇄 할로겐알킬을 나타내거나; 각각 알킬부분에 탄소원자 1 내지 4개를 갖는 직쇄 또는 측쇄 알콕시알킬을 나타내거나; 탄소수 1 내지 6의 직쇄 또는 측쇄 알콕시를 나타내거나; 각각 탄소원자 3 내지 7개를 갖는 사이클로알킬 또는 사이클로알콕시를 나타내거나; 아릴 부위에 각각 탄소원자 6 내지 10개를 갖고, 경우에 따라 직쇄 또는 측쇄 알킬부위에 탄소원자 1 내지 3개를 가지며 각각 아릴부위에서 할로겐, 시아노, 니트로, 탄소수 1 내지 4의 직쇄 또는 측쇄 알킬, 탄소수 1 내지 4의 직쇄 또는 측쇄 알콕시, 탄소수 1 내지 4의 직쇄 또는 측쇄 알킬티오 및 탄소원자 1 내지 4개와 같거나 다른 할로겐원자 1 내지 9개를 갖는 할로겐알킬)중에서 선택된 같거나 다른 치환체로 임의로 일치환되거나 다치환된 아르알킬, 아르알콕시, 아릴 또는 아릴옥시를 나타내고,R4는 아미노를 나타내거나, 각각 알킬 부위에 탄소원자 4개 이하를 갖는 직쇄 또는 측쇄알킬, 알킬아미노, 디알킬아미노 또는 할로겐알킬(이 할로겐알킬은 같거나 다른 할로겐원자 9개 이하를 갖는다)를 나타내며, n은 0,1 또는 2를 나타내는데, 단, R이 시아노를 나타냄과 동시에 X가 아지도 그룹을 나타내는 경우, Ar은 비치환된 페닐을 나타내지 않고 또한 5-니트로-2-피리딜을 나타내지 않는다.
- 제1항에 있어서, 기의 정의가 하기와 같은 일반식(I)의 1-아릴-피리존을 제조하는 방법: R은 시아노 또는 니트로를 나타내고, Ar은 같거나 다른 치환체에 의해 임의로 일-,이-,삼-,사- 또는 오치환된 페닐을 나타내거나, 같거나 다른 치환체로 임의로, 일-,이-, 삼, 또는 사치환된 2-피리딜을 나타내며, 여기에서 각각의 경우에 가능한 치환체는 시아노, 니트로, 플루오로, 클로로, 브로모, 요오도, 메틸, 에틸, n- 및 i-프로필, n-, 이소-, 2급-, 3급-부틸, 메톡시, 에톡시, 메톡시카보닐, 에톡시카보닐, 트리플루오로메틸, 트리클로로메틸, 디클로로플루오로메틸, 디플루오로클로로메틸, 클로로메틸, 디클로로메틸, 디플루오로메틸, 펜타플루오로에틸, 테트라플루오로에틸, 트리플루오로클로로에틸, 트리플루오로에틸, 디플루오로디클로로에틸, 트리플루오로디클로로에틸, 펜타클로로에틸, 트리플루오로메톡시, 트리클로로메톡시, 디클로로플루오로메톡시, 디플루오로클로로메톡시, 클로로메톡시, 디클로로메톡시, 디플루오로메톡시, 펜타플루오로에톡시, 테트라플루오로에톡시, 트리플루오로클로로에톡시, 트리플루오로에톡시, 디플루오로디클로로에톡시, 트리플루오로의클로로에톡시, 펜타클로로에톡시 및 라디칼 -S(O)m-R4이고, X는 아지도 그룹을 나타내거나 라디칼을 나타내고, R1,R2및 R3는 서로 독립적으로, 각각 메틸, 에틸, n-또는 이소-프로필, n-, 이소-, 2급-, 또는 3급-부틸, 알릴, 프로파길, 클로로메틸, 디클로로메틸, 트리클로로메틸, 플루오로메틸, 디클로로플루오로, 트리플루오로메틸, 디클로로플루오로메틸, 디플루오로클로로메틸, 클로로에틸, 트리클로로에틸, 펜타클로로에틸, 트리플루오로에틸, 펜타플루오로에틸, 브로모에틸, 메톡시메틸, 메톡시에틸, 에톡시메틸, 에톡시에틸, n-프로폭시메틸, 이소-프로폭시메틸, n-프로폭시에틸, 이소-프로폭시에틸, 메톡시, 에톡시, n- 또는 이소-프로폭시, n-, 이소-,2급- 또는 3급-부톡시, 사이클로프로필, 사이클로펜틸, 사이클로헥실 또는 사이클로헥실-옥시를 나타내거나; 각각 불소, 염소, 브롬, 시아노, 니트로, 메틸, 에틸, 메톡시, 메틸티오 및 트리플루오로메틸 중에서 선택된 같거나 다른 치환체로 임의로 일-,이-,삼-, 사- 또는 오치환된 벤질, 벤질옥시, 페닐 또는 페녹시를 나타내고, R4는 아미노, 메틸아미노, 에틸아미노, 디메틸아미노, 디에틸아미노, 플루오로디클로로메틸, 디플루오로메틸, 테트라플루오로에틸, 트리클로로에틸, 트리플루오로메틸, 메틸 또는 에틸을 나타내며, n은 0,1 또는 2를 나타내는데, 단, R이 시아노를 나타냄과 동시에 X가 아지도 그룹을 나타내는 경우, Ar은 비치환된 페닐을 나타내지 않고 또한 5-니트로-2-피리딜을 나타내지 않는다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853545347 DE3545347A1 (de) | 1985-12-20 | 1985-12-20 | 1-aryl-pyrazole |
| DEP3545347.8 | 1985-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR870006006A true KR870006006A (ko) | 1987-07-08 |
Family
ID=6289116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR860011007A KR870006006A (ko) | 1985-12-20 | 1986-12-20 | 1-아릴-피라졸의 제조 방법 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4770688A (ko) |
| EP (1) | EP0226156A3 (ko) |
| JP (1) | JPS62164670A (ko) |
| KR (1) | KR870006006A (ko) |
| AU (1) | AU586307B2 (ko) |
| BR (1) | BR8606321A (ko) |
| DD (1) | DD256640A5 (ko) |
| DE (1) | DE3545347A1 (ko) |
| DK (1) | DK617886A (ko) |
| HU (1) | HU198187B (ko) |
| IL (1) | IL81007A0 (ko) |
| NZ (1) | NZ218684A (ko) |
| ZA (1) | ZA869549B (ko) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3539844A1 (de) * | 1985-11-09 | 1987-05-14 | Bayer Ag | Substituierte 5-amino-1-aryl-pyrazole |
| GB8816915D0 (en) * | 1988-07-15 | 1988-08-17 | May & Baker Ltd | New compositions of matter |
| US5198014A (en) * | 1991-11-20 | 1993-03-30 | Fmc Corporation | Herbicidal beta-pyrazolylacrylic acid compound |
| AU2011349461A1 (en) | 2010-12-21 | 2013-06-27 | Bayer Cropscience Lp | Sandpaper mutants of Bacillus and methods of their use to enhance plant growth, promote plant health and control diseases and pests |
| BR112014005654A2 (pt) | 2011-09-12 | 2017-03-28 | Bayer Cropscience Lp | métodos para melhorar a saúde e promover o crescimento de uma planta e/ou de melhorar o amadurecimento da fruta |
| EP2844651A1 (en) | 2012-05-04 | 2015-03-11 | Basf Se | Substituted pyrazole-containing compounds and their use as pesticides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL38312A (en) * | 1970-12-15 | 1974-10-22 | Agripat Sa | Pyridazone derivatives,their production and their use as herbicides |
| MA19540A1 (fr) * | 1981-07-17 | 1983-04-01 | May & Baker Ltd | Derives du n-phenylpyrazole |
| GB2123420B (en) * | 1982-07-15 | 1986-03-26 | May And Barker Limited | Herbicidal n-phenylpyrazole derivatives |
| EP0111453A1 (de) * | 1982-12-10 | 1984-06-20 | Ciba-Geigy Ag | Amid-Verbindungen |
| GB2136427B (en) * | 1983-03-09 | 1986-07-09 | May & Baker Ltd | Herbicidal n-pyridylpyrazole derivatives |
-
1985
- 1985-12-20 DE DE19853545347 patent/DE3545347A1/de not_active Withdrawn
-
1986
- 1986-12-08 EP EP86117018A patent/EP0226156A3/de not_active Withdrawn
- 1986-12-16 US US06/942,141 patent/US4770688A/en not_active Expired - Fee Related
- 1986-12-17 IL IL81007A patent/IL81007A0/xx unknown
- 1986-12-17 NZ NZ218684A patent/NZ218684A/xx unknown
- 1986-12-18 DD DD86297905A patent/DD256640A5/de not_active IP Right Cessation
- 1986-12-19 JP JP61301823A patent/JPS62164670A/ja active Pending
- 1986-12-19 DK DK617886A patent/DK617886A/da not_active Application Discontinuation
- 1986-12-19 ZA ZA869549A patent/ZA869549B/xx unknown
- 1986-12-19 BR BR8606321A patent/BR8606321A/pt unknown
- 1986-12-19 HU HU865348A patent/HU198187B/hu not_active IP Right Cessation
- 1986-12-20 KR KR860011007A patent/KR870006006A/ko not_active Application Discontinuation
- 1986-12-22 AU AU66867/86A patent/AU586307B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ZA869549B (en) | 1988-04-27 |
| EP0226156A2 (de) | 1987-06-24 |
| EP0226156A3 (de) | 1987-08-26 |
| HU198187B (en) | 1989-08-28 |
| DK617886D0 (da) | 1986-12-19 |
| IL81007A0 (en) | 1987-03-31 |
| AU6686786A (en) | 1987-06-25 |
| HUT43044A (en) | 1987-09-28 |
| AU586307B2 (en) | 1989-07-06 |
| JPS62164670A (ja) | 1987-07-21 |
| DD256640A5 (de) | 1988-05-18 |
| NZ218684A (en) | 1989-08-29 |
| DE3545347A1 (de) | 1987-07-02 |
| BR8606321A (pt) | 1987-10-06 |
| DK617886A (da) | 1987-06-21 |
| US4770688A (en) | 1988-09-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR870007134A (ko) | 5-아실아미도-1-아릴-피라졸의 제조방법 | |
| KR870007133A (ko) | 1-아릴피라졸의 제조방법 | |
| KR870001192A (ko) | 신규한(4-치환-피페라진일) 피리다진류의 제조방법 | |
| KR870007891A (ko) | 1-아릴피라졸의 제조방법 | |
| CA2138452A1 (en) | Substituted 1-arylpyrazoles | |
| KR870006006A (ko) | 1-아릴-피라졸의 제조 방법 | |
| DE69526453D1 (de) | 8-alkoxychinoloncarbonsäurehydrat mit ausgezeichneter stabilität und ein verfahren zu seiner herstellung | |
| KR960701018A (ko) | 제초성의 헤테로사이클릭-치환된 피리딘(Herbicidal heterocyclic-substituted pyridines) | |
| KR870003993A (ko) | 1-아릴-4-니트로-피라졸의 제조방법 | |
| KR840004748A (ko) | 2-페닐이미다조[4,5-c]피리딘의 제조방법 | |
| KR890000432A (ko) | 치환된 5-메틸아미노-1-아릴피라졸 | |
| HUT36347A (en) | Herbicides consisting of - as reagent - substituted 5-/acil-amino/-1-phenil-pirozol and process for production of 5-/acil-amino/of derivatives consisting of 5-/acil-amino/-1-phenil pirasol | |
| KR870003984A (ko) | N-치환 디페닐피페리딘의 제조방법 | |
| KR870006003A (ko) | 5-퍼플루오로아실아미노-4-니트로-1-아릴피라졸 염의 제조방법 | |
| KR870002082A (ko) | 1-아릴- 피라졸의 제조 방법 | |
| KR850003716A (ko) | 치환 및 미치환된 2-카바모일니코틴산과 3-퀴놀린카르복실산의 제조방법 | |
| ATE47843T1 (de) | Heteroaromatische ether als herbizide. | |
| KR900003161A (ko) | 치환된 디옥솔란, 이의 제조방법 및 살균제로서의 이의 용도 | |
| KR870004963A (ko) | 1-아릴- 피라졸의 제조방법 | |
| KR920702357A (ko) | 퀴놀린 유도체의 제조방법 | |
| KR910000656A (ko) | N-페닐피라졸 유도체 | |
| KR850000397A (ko) | 1,4-디하이드로 피리딘의 제조방법 | |
| KR890002207A (ko) | I- 아릴피라졸 | |
| GB1527807A (en) | Thiazolines | |
| KR870002079A (ko) | 1-아릴-5 하이드라지노- 피라졸의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |