KR840007578A - 치환된 니트로 및 시아노구아니딘류의 제조방법 - Google Patents

치환된 니트로 및 시아노구아니딘류의 제조방법 Download PDF

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KR840007578A
KR840007578A KR1019830006000A KR830006000A KR840007578A KR 840007578 A KR840007578 A KR 840007578A KR 1019830006000 A KR1019830006000 A KR 1019830006000A KR 830006000 A KR830006000 A KR 830006000A KR 840007578 A KR840007578 A KR 840007578A
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och
halogen
hydrogen
alkyl
reaction mixture
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KR1019830006000A
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메리 스펠츠 로라인 (외 2)
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죤 제이 헤이간
아메리칸 사이아나밋드 캄파니
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Publication of KR840007578A publication Critical patent/KR840007578A/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
    • 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
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Luminescent Compositions (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Pyrane Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

내용 없음.

Description

치환된 니트로 및 시아노구아니딘류의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 N6-벤질아데닌 및 본 발명의 화합물인 1-니트로-3-(p,α,α,4-테트라플루오로-m-톨릴)구아니딘의 투여에 반응하여 얻어진 엽록소 생합성율의 증가를 나타내는 그래프(663nm에서 침출액을 흡수).
제2도는 M6-벤질아데닌 및 1-니트로-3-(α,α,α,4-테트라플루오로-m-톨릴]구아니딘의 투여에 반응하여 얻어진 떡잎면적의 증가를 나타내는 그래프.

Claims (13)

  1. 다음 구조식(A)의 적절히 치환된 아닐린과 다음 구조식(B)의 N-알킬-N-니트로소-N′-니트로구아니딘의 대략 등몰량을 알코올 수용액내에서 반응시키고, 이 반응혼합물을 40℃로 가열하고, 이와같이 가열된 반응혼합물을 강염기로 처리하고, 이 반응혼합물로부터 알코올을 제거하고, 나머지 잔류물을 산성화시키고, 그후 임의로는 이 화합물을 요오드화메틸 및 산화은으로 처리하여서 R이 CH3인 대응 화합물을 얻는 것을 특징으로 하는, 다음 구조식(I)의 화합물의 제조방법.
  3. 상기 식에서, X1은 COCH3, 할로겐, CN, CH2CN, C(OH)2CF3, OCHF2, OCF3, CH3, SCH3, CF3, NO2, OCF2CHF2, OCH|3, N(CH)2, COOCH3, 혹은 CH2OR3(여기서 R3은 H 혹은 CH3임)이고; Y1은 H, 할로겐, 혹은 CH3이며; Z1은 H, CH3, 할로겐 OCH3, 혹은 CF3이고; R1은 H 혹은 CH3이다.(단, X1이 CH3, OCH3, F, Cl 혹은 Br이고 R이 H인 경우에는 Y1과 Z) 모두가 수소일 수 없으며; X1이 Cl이고 Z1과 R이 각각 수소인 경우에는 Y1이 CH3일 수 없다.) R′는 C1-C알킬이다.
  4. 다음 구조식(C)의 화합물을 물과 같은 용매내에서 니트로구아니딘과 반응시키고, 이 반응혼합물을 1시간동안 50℃-75℃로 가열함을 특징으로 하는, 다음 구조식(II)의 화합물의 제조방법.
  6. 상기식에서, X2는 H, OH, 직쇄 혹은 측쇄의 C1-C4알콕시, SCH3, 할로겐, OCF3, CF3, 직쇄 혹은 측쇄의 C1-C4알킬, 또는, 테트라하이드로-2H-피란-2-일이고; Y2는 H 혹은 F이며; Z2는 F, H, CH3, 혹은 OCH3이고; W2는 H 혹은 F이며; m은 0, 1, 혹은 2의 정소이고; R2는 H, CH3, H5, 혹은 CF3이다.(단, m이 0이고 R2가 H 혹은 CH3인 경우에는 W2, X2, Y2, Z2가 모두 수소일 수는 없으며; m이 1일 경우에는 R2, W2, X2, Y2, Z2가 모두 수소일 수는 없다).
  7. 다음 구조식(D)의 적절히 치환된 아닐린을 강한 무기산에 분산시키고, 이와같이 형성된 반응혹합물을 적어도 등몰량의 나트륨디시안아아미드와 물속에서 혼합함을 특징으로 하는, 다음 구조식(III)의 화합물의 제조방법.
  9. 상기 식에서, X3은 OCH3, CH3, 할로겐, 혹은 CF3이고; Y3은 H, OH, 혹은 할로겐이며; Z2는 H 혹은 Cl이다.(단, Y3및 Z3은 X3이 OCH3인 경우에 한하여 모두 수소일 수 있으며; X3과 Y3이 각각 Cr, Cr3, 혹은 I인 경우에는 Z3이 수소일 수 없고; X3가 CH3이고 Z3이 H인 경우에는 Y3이 Cl일 수 없다).
  10. 다음 구조식(E)의 적절히 치환된 벤질아민을 강한 무기산에 분산시키고, 이와 같이 형. 된 반응혼합물을 적어도 등몰량의 나트륨디시안아미드와 물속에서 혼합함을 특징으로 하는, 다음 구조식(IV)의 화합물의 제조방법.
  12. 상기 식에서, W4는 H 혹은 F이고; X4는 직쇄 혹은 측쇄의 C1-C4알콕시, 직쇄 혹은 측쇄의 C1-C4알킬, 혹은 F이다.(단, W4가 H이면 W4가 H이고, W4가 H이면 X4가 C1-C4알콕시, C1-C4알킬, 혹은 F이다).
  13. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019830006000A 1982-12-20 1983-12-19 치환된 니트로 및 시아노구아니딘류의 제조방법 KR840007578A (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US45169882A 1982-12-20 1982-12-20
US45169 1982-12-20

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KR840007578A true KR840007578A (ko) 1984-12-08

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EP (2) EP0113070B1 (ko)
JP (1) JPS59118757A (ko)
KR (1) KR840007578A (ko)
AT (1) ATE31920T1 (ko)
AU (2) AU565227B2 (ko)
BR (1) BR8306966A (ko)
DD (1) DD225988A5 (ko)
DE (1) DE3345281A1 (ko)
DK (1) DK585083A (ko)
ES (3) ES528171A0 (ko)
FI (1) FI834676A (ko)
HU (1) HU195637B (ko)
IL (1) IL70432A0 (ko)
NZ (1) NZ206556A (ko)
PH (1) PH21256A (ko)
ZA (1) ZA839399B (ko)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4822408A (en) * 1985-07-29 1989-04-18 American Cyanamid Company Alkyl-, alkenyl- and alkynylnitroguanidines as cytokinin plant growth regulants
US4995903A (en) * 1985-07-29 1991-02-26 American Cyanamid Company Alkyl-, Alkenyl- and alkynylnitroguanidines as cytokinin plant growth regulants
US4639268A (en) * 1985-07-29 1987-01-27 American Cyanamid Company Nitro- and cyanoguanidines as selective preemergence herbicides and plant defoliants
US4677226A (en) * 1985-07-29 1987-06-30 American Cyanamid Company Alkyl-, alkenyl- and alkynylnitroguanidines as cytokinin plant growth regulants
IE960441L (en) * 1988-12-27 1990-06-27 Takeda Chemical Industries Ltd Guanidine derivatives, their production and insecticides
JP2749639B2 (ja) * 1989-06-28 1998-05-13 鐘紡株式会社 シアノグアニジン誘導体
DE3929582A1 (de) * 1989-09-06 1991-03-07 Hoechst Ag Benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltendes medikament
CO5231151A1 (es) 1999-10-13 2002-12-27 Novartis Ag Metodo para mejorar el crecimiento de las plantas

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB978855A (en) * 1960-04-18 1964-12-23 Sterling Drug Inc 1,1-(alkylene)bis(5-arylbiguanides), acid-addition salts thereof, and disinfecting oranitizing compositions containing same
DE1568581C3 (de) * 1966-09-08 1974-08-15 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung substituierter Cyano-Guanidine
DE3014353A1 (de) * 1980-04-15 1982-01-21 Bayer Ag, 5090 Leverkusen Trisubstituierte cyanguanidine, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide

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ES8601115A1 (es) 1985-11-16
FI834676A0 (fi) 1983-12-19
HU195637B (en) 1988-06-28
AU565227B2 (en) 1987-09-10
ES528171A0 (es) 1985-11-16
DK585083A (da) 1984-06-21
ES543758A0 (es) 1986-01-16
ATE31920T1 (de) 1988-01-15
DE3345281A1 (de) 1984-06-20
BR8306966A (pt) 1984-07-24
ZA839399B (en) 1984-08-29
ES8604120A1 (es) 1986-01-16
DD225988A5 (de) 1985-08-14
AU7556787A (en) 1987-10-22
NZ206556A (en) 1988-02-12
ES543756A0 (es) 1986-10-16
EP0113070B1 (en) 1988-01-13
PH21256A (en) 1987-08-31
AU2251583A (en) 1984-06-28
EP0189579A1 (en) 1986-08-06
IL70432A0 (en) 1984-03-30
DK585083D0 (da) 1983-12-19
ES8700229A1 (es) 1986-10-16
JPS59118757A (ja) 1984-07-09
EP0113070A1 (en) 1984-07-11
FI834676A (fi) 1984-06-03

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