PL138343B1 - Process for preparing novel derivatives of 5-methylthiopyrimidine and fungicide containg those derivatives as an active substances - Google Patents

Process for preparing novel derivatives of 5-methylthiopyrimidine and fungicide containg those derivatives as an active substances Download PDF

Info

Publication number: PL138343B1
Authority: PL; Poland
Prior art keywords: group; formula; compound; methyl; phenyl
Prior art date: 1982-01-20

Application number

PL1983240209A

Other languages

English (en)

Polish (pl)

Other versions

PL240209A1 (en

Inventor

Katsutoshi Ishikawa

Hitoshi Shimotori

Noboru Iida

Kazuno Akihiro

Shuji Ozawa

Original Assignee

Mitsui Toatsu Kagaku Kk

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-01-20

Filing date

1983-01-18

Publication date

1986-09-30

1983-01-18 Application filed by Mitsui Toatsu Kagaku Kk filed Critical Mitsui Toatsu Kagaku Kk

1984-06-18 Publication of PL240209A1 publication Critical patent/PL240209A1/xx

1986-09-30 Publication of PL138343B1 publication Critical patent/PL138343B1/pl

Links

239000013543 active substance Substances 0.000 title claims description 39
239000000417 fungicide Substances 0.000 title claims description 13
230000000855 fungicidal effect Effects 0.000 title claims description 11
IBMKUYMVNFUNOW-UHFFFAOYSA-N 5-methylsulfanylpyrimidine Chemical class CSC1=CN=CN=C1 IBMKUYMVNFUNOW-UHFFFAOYSA-N 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 90
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
238000000034 method Methods 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 15
-1 aminocarbonylalkyyl Chemical group 0.000 claims description 15
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000004103 aminoalkyl group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 6
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000004615 ingredient Substances 0.000 claims description 5
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125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 claims description 3
229910052736 halogen Chemical group 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
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125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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229910021641 deionized water Inorganic materials 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000002316 fumigant Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004571 lime Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000005445 natural material Substances 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
244000144977 poultry Species 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000008719 thickening Effects 0.000 description 1
QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
150000003752 zinc compounds Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- 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
- C07D239/60—Three or more oxygen or sulfur atoms
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

PL1983240209A 1982-01-20 1983-01-18 Process for preparing novel derivatives of 5-methylthiopyrimidine and fungicide containg those derivatives as an active substances PL138343B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57006142A JPS58124773A (ja)	1982-01-20	1982-01-20	５−メチルチオピリミジン誘導体とその製造法と農園芸用殺菌剤

Publications (2)

Publication Number	Publication Date
PL240209A1 PL240209A1 (en)	1984-06-18
PL138343B1 true PL138343B1 (en)	1986-09-30

Family

ID=11630260

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL1983240209A PL138343B1 (en)	1982-01-20	1983-01-18	Process for preparing novel derivatives of 5-methylthiopyrimidine and fungicide containg those derivatives as an active substances

Country Status (11)

Country	Link
US (1)	US4540698A (2)
JP (1)	JPS58124773A (2)
DD (2)	DD219654A5 (2)
DE (1)	DE3301106A1 (2)
FR (1)	FR2519983B1 (2)
GB (1)	GB2113216B (2)
IN (1)	IN157931B (2)
IT (1)	IT1163039B (2)
NL (1)	NL8300193A (2)
PL (1)	PL138343B1 (2)
RO (4)	RO89714A (2)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59227867A (ja) *	1983-06-09	1984-12-21	Mitsui Toatsu Chem Inc	５―メチルチオピリミジン誘導体とその製造法と農園芸用殺菌剤
JPH0635450B2 (ja) *	1984-03-16	1994-05-11	三井東圧化学株式会社	チオシアノピリミジン誘導体、その製造法および農園芸用殺菌剤
JPS6345269A (ja) *	1986-04-28	1988-02-26	Mitsui Toatsu Chem Inc	ジハロゲン置換チオシアノピリミジン誘導体、その製造法および農園芸用殺菌剤
JPS63112566A (ja) *	1986-10-28	1988-05-17	Nissan Chem Ind Ltd	ピリミジノン誘導体、その製法および殺虫・殺ダニ・殺菌剤
JPH0827122A (ja) *	1994-07-15	1996-01-30	Kureha Chem Ind Co Ltd	２−（ベンジルオキシ）（フェノキシ）ピリミジン誘導体、その製造方法及び除草剤
CN1129584C (zh) *	1996-10-31	2003-12-03	组合化学工业株式会社	嘧啶氧基链烷酰胺衍生物及农业和园艺用杀菌剂
EP1317450B1 (en) *	2000-09-15	2006-11-22	Vertex Pharmaceuticals Incorporated	Pyrazole compounds useful as protein kinase inhibitors
US6660731B2 (en) *	2000-09-15	2003-12-09	Vertex Pharmaceuticals Incorporated	Pyrazole compounds useful as protein kinase inhibitors
US7473691B2 (en) *	2000-09-15	2009-01-06	Vertex Pharmaceuticals Incorporated	Pyrazole compounds useful as protein kinase inhibitors
NZ526472A (en) *	2000-12-21	2004-04-30	Vertex Pharma	Pyrazole compounds useful as protein kinase inhibitors
EP1472245A2 (en) *	2002-02-06	2004-11-03	Vertex Pharmaceuticals Incorporated	Heteroaryl compounds useful as inhibitors of gsk-3
AU2003218215A1 (en) *	2002-03-15	2003-09-29	Vertex Pharmaceuticals, Inc.	Azolylaminoazines as inhibitors of protein kinases
MY141867A (en) *	2002-06-20	2010-07-16	Vertex Pharma	Substituted pyrimidines useful as protein kinase inhibitors
DK1532145T3 (da) *	2002-08-02	2007-01-15	Vertex Pharma	Pyrazolpræparater der er anvendelige som inhibitorer af GSK-3
WO2004072029A2 (en) *	2003-02-06	2004-08-26	Vertex Pharmaceuticals Incorporated	Pyrazolopyridazines useful as inhibitors of protein kinases
AU2004297235A1 (en) *	2003-12-04	2005-06-23	Vertex Pharmaceuticals Incorporated	Quinoxalines useful as inhibitors of protein kinases
AU2006279376B2 (en) *	2005-08-18	2011-04-14	Vertex Pharmaceuticals Incoporated	Pyrazine kinase inhibitors
EP1954277B1 (en) *	2005-11-03	2017-01-18	Vertex Pharmaceuticals Incorporated	Aminopyrimidines useful as kinase inhibitors
MX2009004807A (es) *	2006-11-02	2009-06-15	Vertex Pharma	Aminopiridinas y aminopirimidinas utiles como inhibidores de proteina cinasa.
NZ577768A (en) *	2006-12-19	2012-01-12	Vertex Pharma	Aminopyrimidines useful as inhibitors of protein kinases
ATE526328T1 (de) *	2007-03-09	2011-10-15	Vertex Pharma	Als inhibitoren von proteinkinasen geeignete aminopyrimidine
MX2009009590A (es) *	2007-03-09	2009-11-10	Vertex Pharma	Aminopirimidinas utiles como inhibidores de proteinas cinasas.
MX2009009592A (es) *	2007-03-09	2009-11-10	Vertex Pharma	Aminopiridinas utiles como inhibidores de proteinas cinasas.
AU2008240313A1 (en)	2007-04-13	2008-10-23	Aj Park	Aminopyrimidines useful as kinase inhibitors
JP5389786B2 (ja) *	2007-05-02	2014-01-15	バーテックスファーマシューティカルズインコーポレイテッド	キナーゼ阻害として有用なアミノピリミジン
CN101679387A (zh) *	2007-05-02	2010-03-24	沃泰克斯药物股份有限公司	可用作激酶抑制剂的氨基嘧啶类化合物
AU2008247592A1 (en)	2007-05-02	2008-11-13	Vertex Pharmaceuticals Incorporated	Thiazoles and pyrazoles useful as kinase inhibitors
MX2009012719A (es) *	2007-05-24	2010-02-04	Vertex Pharma	Tiazoles y pirazoles utiles como inhibidores de cinasa.
CN101790532B (zh) *	2007-07-31	2013-11-20	沃泰克斯药物股份有限公司	5-氟-1H-吡唑并[3，4-b]吡啶-3-胺及其衍生物的制备方法
WO2010027921A1 (en) *	2008-09-03	2010-03-11	Vertex Pharmaceuticals Incorporated	Co-crystals and pharmaceutical formulations comprising the same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4199583A (en) *	1970-07-13	1980-04-22	The Upjohn Company	Antifungal method, formulations and compounds
US4126459A (en) *	1976-05-14	1978-11-21	Polaroid Corporation	Thioether substituted silver halide solvents
US4211559A (en) *	1976-09-30	1980-07-08	Texas Instruments Incorporated	Photographic processes and compositions employing thioether containing silver halide solvents

1982
- 1982-01-20 JP JP57006142A patent/JPS58124773A/ja active Granted
1983
- 1983-01-04 IN IN14/CAL/83A patent/IN157931B/en unknown
- 1983-01-07 GB GB08300400A patent/GB2113216B/en not_active Expired
- 1983-01-14 US US06/457,917 patent/US4540698A/en not_active Expired - Fee Related
- 1983-01-14 DE DE19833301106 patent/DE3301106A1/de not_active Withdrawn
- 1983-01-17 RO RO83116655A patent/RO89714A/ro unknown
- 1983-01-17 RO RO109750A patent/RO86363B/ro unknown
- 1983-01-17 RO RO83116657A patent/RO89716A/ro unknown
- 1983-01-17 RO RO83116656A patent/RO89715A/ro unknown
- 1983-01-18 IT IT19164/83A patent/IT1163039B/it active
- 1983-01-18 PL PL1983240209A patent/PL138343B1/pl unknown
- 1983-01-19 NL NL8300193A patent/NL8300193A/nl not_active Application Discontinuation
- 1983-01-19 DD DD83260099A patent/DD219654A5/de unknown
- 1983-01-19 DD DD83247352A patent/DD209447A5/de unknown
- 1983-01-20 FR FR8300880A patent/FR2519983B1/fr not_active Expired

Also Published As

Publication number	Publication date
JPH0378383B2 (2)	1991-12-13
GB8300400D0 (en)	1983-02-09
FR2519983B1 (fr)	1985-12-06
RO89714A (ro)	1986-07-30
RO86363A (ro)	1985-03-15
FR2519983A1 (fr)	1983-07-22
RO89716A (ro)	1986-07-30
GB2113216B (en)	1985-12-04
RO86363B (ro)	1985-03-31
RO89715A (ro)	1986-07-30
US4540698A (en)	1985-09-10
DE3301106A1 (de)	1983-07-28
PL240209A1 (en)	1984-06-18
IT1163039B (it)	1987-04-08
DD209447A5 (de)	1984-05-09
GB2113216A (en)	1983-08-03
JPS58124773A (ja)	1983-07-25
IT8319164A0 (it)	1983-01-18
NL8300193A (nl)	1983-08-16
DD219654A5 (de)	1985-03-13
IN157931B (2)	1986-07-26

Publication	Publication Date	Title
PL138343B1 (en)	1986-09-30	Process for preparing novel derivatives of 5-methylthiopyrimidine and fungicide containg those derivatives as an active substances
US3856814A (en)	1974-12-24	Olan-2-ylidenemalonates
CS21592A3 (en)	1992-08-12	Novel sulfonyl ureas
NZ188440A (en)	1984-07-06	1,2-dichloro-cyanovinyl sulphides and fungicidal compositions
KR900006835B1 (ko)	1990-09-22	피리다지논 유도체의 제조방법
US4741768A (en)	1988-05-03	Herbicidal substituted 2-[1-(3-trans-chloro-allyloxyamino)alkylidene]-cyclohexane dione salts
EP0224842A2 (en)	1987-06-10	Pyrazolesulfonamide derivative, process for its production and herbicide containing it
US4482740A (en)	1984-11-13	5-Phenylcyclohexenone derivatives
PL120535B1 (en)	1982-03-31	Pesticide or plant growth regulator and process for manufacturing sulfonanilidesenijj i sposob poluchenija sul'fonanilidov
US4626273A (en)	1986-12-02	Herbicidal novel 2-alkoxyaminosulfonyl-benzene-sulfonylureas
EP0272855A1 (en)	1988-06-29	Herbicidal pyridine sulfonamides
EP0007020B1 (de)	1981-10-14	Organische Phosphorsäureester, Verfahren zu ihrer Herstellung, ihre Verwendung, Schädlingsbekämpfungsmittel und ihre Herstellung
CA2684944A1 (en)	2008-11-27	Pesticidal diazene oxide carboxylates
SU1355125A3 (ru)	1987-11-23	Способ получени производных тиоцианопиримидина
CA2042660A1 (en)	1991-11-18	Herbicidal sulfonylurea derivatives
US4113724A (en)	1978-09-12	Arylthiodicyanopyrazines as plant disease control agents
DE69009679T2 (de)	1995-02-02	Benzylidenaminooxyalkan(thio)carbonsäureamidderivate, Verfahren zu deren Herstellung und Herbizide.
JPH07504173A (ja)	1995-05-11	除草剤としてのスルホニル尿素
PL82655B1 (2)	1975-10-31
EP0097270B1 (de)	1985-08-28	Organophosphat-Derivate
JPH0495077A (ja)	1992-03-27	２―ヨードプロパルギルオキシピリミジン誘導体及び農園芸用殺菌剤
JPS6160659A (ja)	1986-03-28	置換フエニルスルホニルアゾ−ル、その製法及び農園芸用殺菌剤
US3711580A (en)	1973-01-16	O-chloro-substituted alkyl-s-alkyl-s-benzyl-phosphoro-dithiolates
US4431659A (en)	1984-02-14	1-(Aryl)thiocarbamoyl-2-(aryl)-3-pyrazolidinones and their nematicidal use
JPS59222492A (ja)	1984-12-14	ピラノピラゾ−ル誘導体