KR830006896A - 페닐피리딘의 제조방법과 살초제의 식물독 - Google Patents
페닐피리딘의 제조방법과 살초제의 식물독 Download PDFInfo
- Publication number
- KR830006896A KR830006896A KR1019810005105A KR810005105A KR830006896A KR 830006896 A KR830006896 A KR 830006896A KR 1019810005105 A KR1019810005105 A KR 1019810005105A KR 810005105 A KR810005105 A KR 810005105A KR 830006896 A KR830006896 A KR 830006896A
- Authority
- KR
- South Korea
- Prior art keywords
- halogen
- alkyl
- formula
- hydrogen
- phenyl
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims abstract 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 title 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 title 1
- 230000002363 herbicidal effect Effects 0.000 title 1
- 239000003123 plant toxin Substances 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims abstract 10
- 150000002367 halogens Chemical class 0.000 claims abstract 10
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 claims abstract 3
- -1 nitroanilides Chemical class 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 231100000674 Phytotoxicity Toxicity 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract 2
- 239000000729 antidote Substances 0.000 abstract 2
- 229940075522 antidotes Drugs 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 abstract 1
- 230000000885 phytotoxic effect Effects 0.000 abstract 1
- 239000002689 soil Substances 0.000 abstract 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 abstract 1
- 150000003918 triazines Chemical class 0.000 abstract 1
Classifications
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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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- 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
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Peptides Or Proteins (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Catching Or Destruction (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Liquid Crystal Substances (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (2)
- 하기 구조식(Ⅱ)의 페닐아미딘을 염기존재하의 알콜 용액에서 하기 구조식(Ⅲ)의 디에틸 말로네이트로 축합한 다음, 필요하다면, 형성된 하기 구조식(Ⅳ)의 2-페닐-4,6-디하이드록시피리미딘의 히드록실기를 할로겐원자(할로겐화제 이용)로 치환한 다음, 필요하다면, 이들 할로겐원자를 다시 자디몰 R1및 R3로 치환하는 것을 특징으로 하여 상기 구조식(Ⅰ)의 페닐피리미딘의 제조방법 :상기 식에서n은 1-5이고,R은 수소, 할로겐, 니트로, 시아노, -XR5, -NR6R7, -CO-A, -CS-NR6R7, -SO2-NR6R7,-PO(OR402, -SO3H, -N=CR8R9, C1-C6알킬, 할로겐, -XR5, -NR6R7, PO(OR4)2, -CO-A 또는 시아노, 또는 C2-C6알케닐로 치환된거나 치환된지 않은 C3-C6알킬 또는 C3-C6시클로알킬기, 할로겐 또는 -XR5로 치환되거나 치환되지 않은 C3-C6시클로알케닐 또는 C2-C6알키닐기이며,R1및 R3는 서로 다르며, 수소, 할로겐, C1-C6알킬, 시아노, -CO-A, -NR6R7, -XR5페닐 또는 할로겐, C1-C4알킬, 니트로 또는 -XR5로 치환된 페닐이며,R2는 수소, 할로겐, 페닐 또는 할로겐, C1-C4알킬, 트르플루오로메틸, 니트로 또는 -XR5- 로 치환된 페닐, 또는 할로겐 또는 -XR5로 치환되거나 치환되지 않은 C1-C6알킬, C3-C6시클로알킬, C2-C6알케닐 또는 C2-C6알키닐이고,R4는 수소 또는 할로겐, -CO-A, 히드록시, C1-C6알콕시 또는 -NR6R7으로 치환되거나 치환되지 않은 C1-C6알킬, C3-C6알케닐 또는 C3-C6알키닐기이며R5는 R4에서와 같고, 부가적으로 C1-C3알킬카르보닐, C3-C6알케닐카르보닐 또는 C3-C6알키닐카르보닐이며,R6및 R7은 각각 서로 다르며, 수소, C3-C6알케닐, C3-C6알키닐, C3-C6시클로 알킬 : 또는 -CO-A 로 치환되거나 치환되지 않은 C1-C6알킬이며 : R6및 R7중 하나는 -CO-A 또는 -OR4기 이거나, 또는 R4및 R7이 모두 산소, 황, 아미노 또는 C1-C4알킬이미노기로 차단될 수 있는 4- 내지 6- 멤버의 알킬렌 쇄이며,B는 직쇄 또는 측쇄의 C1-C6알킬렌이고,X는 산소, 황, -SO- 도는 -SO2-이며,A는 R5에서와 같거나, -OR5또는 NR6R7이며,R8은 C1-C6알콕시로 치환되거나 치환되지 않은 C1-C6알킬이며,R9는 수소 또는 R8에서와 같고,R8과 R9는 함께 4- 내지 5-멤버의 알킬렌 쇄이다.
- 상기 청구범위 1에 따른 구조식 I의 페닐피리미딘 0.1-0.5%, 고체 또는 액체 보조제 1-99%와 계면활성제 0.1-25%로 구성된 것을 특징으로 하는 살초제의 식물독성으로부터 작물을 보호하기 위한 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH952280 | 1980-12-23 | ||
CH9522 | 1980-12-23 | ||
CH9522/80-3 | 1980-12-23 | ||
CH2363 | 1981-04-08 | ||
CH2363/81-3 | 1981-04-08 | ||
CH236381 | 1981-04-08 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR830006896A true KR830006896A (ko) | 1983-10-12 |
KR890001062B1 KR890001062B1 (ko) | 1989-04-22 |
Family
ID=25690262
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019810005105A KR890001062B1 (ko) | 1980-12-23 | 1981-12-23 | 페닐피리딘의 제조방법 및 제초제의 식물독성으로부터 작물을 보호하기 위한 조성물 |
Country Status (30)
Country | Link |
---|---|
US (2) | US4493726A (ko) |
EP (1) | EP0055693B1 (ko) |
KR (1) | KR890001062B1 (ko) |
AT (1) | ATE32065T1 (ko) |
AU (1) | AU558710B2 (ko) |
BG (1) | BG37221A3 (ko) |
BR (1) | BR8108383A (ko) |
CA (1) | CA1220953A (ko) |
CS (1) | CS243465B2 (ko) |
DD (1) | DD202798A5 (ko) |
DE (1) | DE3176621D1 (ko) |
DK (1) | DK156687C (ko) |
DO (1) | DOP1981004033A (ko) |
ES (1) | ES8300322A1 (ko) |
GR (1) | GR76379B (ko) |
HU (1) | HU191339B (ko) |
IL (1) | IL64612A (ko) |
IN (1) | IN159209B (ko) |
MA (1) | MA19355A1 (ko) |
MX (1) | MX6720E (ko) |
MY (1) | MY101392A (ko) |
NZ (1) | NZ199360A (ko) |
OA (1) | OA06972A (ko) |
PH (1) | PH19369A (ko) |
PL (1) | PL130575B1 (ko) |
PT (1) | PT74181B (ko) |
RO (1) | RO83451B (ko) |
SU (1) | SU1482505A3 (ko) |
YU (1) | YU43250B (ko) |
ZW (1) | ZW30681A1 (ko) |
Families Citing this family (104)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3379544D1 (en) * | 1982-06-08 | 1989-05-11 | Ciba Geigy Ag | 2-phenyl-2-naphthyl and 2-heterocyclic pyrimidines as antidotes for protecting cultured plants before phytotoxic damages caused by herbicides |
US4648896A (en) * | 1982-11-15 | 1987-03-10 | Ciba-Geigy Corporation | 2-aryl-4,6-dihalopyrimidines as antidote for protecting cultivated plants from phytotoxic damage caused by herbicides |
DE3315295A1 (de) * | 1983-04-27 | 1984-10-31 | Merck Patent Gmbh, 6100 Darmstadt | Fluorhaltige pyrimidinderivate |
EP0136976A3 (de) * | 1983-08-23 | 1985-05-15 | Ciba-Geigy Ag | Verwendung von Phenylpyrimidinen als Pflanzenregulatoren |
CH659815A5 (de) * | 1984-03-15 | 1987-02-27 | Ciba Geigy Ag | 2-(4'-hydroxymethylphenyl)-pyrimidine. |
US4900813A (en) * | 1987-07-02 | 1990-02-13 | Ciba-Geigy Corporation | Fiber-reactive azo dyes having a 4,6-diaminopyridine coupling component |
US4927826A (en) * | 1987-07-10 | 1990-05-22 | Hoffman-La Roche Inc. | Cycloproylpropenamides useful as platelet activing factor (PAF) antagonists |
US4963676A (en) * | 1988-02-09 | 1990-10-16 | Georgia State University Foundation, Inc. | Di-substituted phthalazines |
US4929726A (en) * | 1988-02-09 | 1990-05-29 | Georgia State University Foundation, Inc. | Novel diazines and their method of preparation |
MX16687A (es) * | 1988-07-07 | 1994-01-31 | Ciba Geigy Ag | Compuestos de biarilo y procedimiento para su preparacion. |
US5201933A (en) * | 1988-08-01 | 1993-04-13 | Monsanto Company | Safening herbicidal benzoic acid derivatives |
GB8909560D0 (en) * | 1989-04-26 | 1989-06-14 | Smith Kline French Lab | Chemical compounds |
WO1992004333A1 (en) * | 1990-08-31 | 1992-03-19 | Nippon Shinyaku Co., Ltd. | Pyrimidine derivative and medicine |
US5395816A (en) * | 1990-12-12 | 1995-03-07 | Imperial Chemical Industries Plc | Antidoting herbicidal 3-ixoxazolidinone compounds |
US5527762A (en) * | 1990-12-12 | 1996-06-18 | Zeneca Limited | Antidoting herbicidal 3-isoxazolidinone compounds |
EP0495749A1 (de) * | 1991-01-14 | 1992-07-22 | Ciba-Geigy Ag | Bipyridyle |
BR9200508A (pt) * | 1991-02-15 | 1992-10-20 | Kumiai Chemical Industry Co | Composicao herbicida na forma de solucao estavel ou concentrado emulsificavel de propanil |
US5541148A (en) * | 1992-07-08 | 1996-07-30 | Ciba-Geigy Corporation | Selective safened herbicidal composition comprising 2-ethoxycarbonyl-3-(4,6-dimethoxypyrimidine-2-yl) oxy-pyridine and an acylsulfamoylphenyl-urea safener |
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