WO1996022980A1 - Nouveaux derives de pyrimidine, bactericide et insecticide - Google Patents

Nouveaux derives de pyrimidine, bactericide et insecticide Download PDF

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Publication number
WO1996022980A1
WO1996022980A1 PCT/JP1996/000129 JP9600129W WO9622980A1 WO 1996022980 A1 WO1996022980 A1 WO 1996022980A1 JP 9600129 W JP9600129 W JP 9600129W WO 9622980 A1 WO9622980 A1 WO 9622980A1
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WO
WIPO (PCT)
Prior art keywords
nhch
group
eny
heny
iso
Prior art date
Application number
PCT/JP1996/000129
Other languages
English (en)
Japanese (ja)
Inventor
Jun Satow
Yasuo Kondo
Yoshihiro Kudo
Takumi Mikashima
Junichi Watanabe
Hiroshi Ohya
Masanori Nishioka
Shigeru Sasabe
Takashi Furusato
Original Assignee
Nissan Chemical Industries, Ltd.
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.)
Filing date
Publication date
Application filed by Nissan Chemical Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to AU44960/96A priority Critical patent/AU4496096A/en
Publication of WO1996022980A1 publication Critical patent/WO1996022980A1/fr

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Classifications

    • 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
    • C07D239/26—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Definitions

  • the present invention relates to a novel pyrimidine derivative and a bactericidal or insecticide containing the derivative as an active ingredient.
  • fungicides have been put into practical use to protect important crops such as rice, fruit trees, vegetables, wheat, corn, soybeans, cotton, beets, etc. from pathogenic bacteria and to increase the productivity of these important crops.
  • These agents can be broadly classified into non-selective and selective fungicides depending on the specific mechanism of action. Further, each of them can be classified into seed treatment type, water surface application type, soil application (soil admixture treatment, soil injection treatment) type, stem vegetable application type, etc. according to the method of applying the medicine.
  • X is a chlorine atom, bromine atom or iodine atom
  • R1 is a hydrogen atom, formyl group, Ci-C 6 alkyl group, Ci-C 6 haloalkyl group, C 3 -C 8 alkenyl group, phenylene group, and display the benzyl group, c 3 -c 8 alkynyl or c 3 -c 6 cycloalkyl group
  • R2 is a hydrogen atom, Ci -C 6 Arukinore group, an optionally substituted phenyl group [location substituent halogen atoms, S0 2 CH 3, SCH 3 , Ci -C 8 alkyl group, Ci -C 8 alkoxy group, Ci -C 8 alkoxy (Ci -C 8) alkoxy groups, Ci -C 4 haloalkoxy groups, Ci - C 4 haloalkyl group, N (CH 3) 2, phenoxy group, phenyl group, benzyl
  • (d-alkyl) is selected from the group optionally), -Q- substituted Hetero ring (Q represents a saturated or unsaturated carbon chain of Ci-C 6 which may be branched, and a hetero ring is a pyridine ring, thiophene ring, thiazole ring, pyridazine ring, pyrazine ring, pyrimidine ring, pyra Tetrazole ring, represents Isookisazoru ring or an imidazole ring, the substituents of heterocycle halogen atom, Ci-C 8 alkyl group, Ci-C 8 alkoxy groups, Ci-C 4 Haroaru kill group, phenyl group, phenoxy group, N 02, CN, C02- (Ci-C 4 alkyl) group, SCH 3, N (CH 3 ) is selected from 2, S0 2 CH 3 optionally.
  • Q represents a saturated or unsaturated carbon chain of Ci-C 6 which may be branched,
  • -Q-0-substituted phenyl group (Q may be Ci-C 6 , which may be branched or saturated or unsaturated carbon chain, and the substituent of the phenyl group may be a hydrogen atom, a halogen atom, S0 2 CH 3, SCH 3, Ci-C 8 alkyl group, Ci-C 8 haloalkoxy group, d-Cs alkoxy group, Ci-C 8 alkoxy (Ci-C 8) alkoxy groups, Ci-C 4 haloalkyl group, N (CH 3) 2, ⁇ 2, phenoxy group, phenyl group, Baie Njiru group, Benjiruokishi group, Benzoiru group, benzenesulfonyl group, CN, C0 2 - (Ci -C4 alkyl) is selected from the group optionally,), -Q- 0-substituted hetero ring (Q represents an optionally branched saturated or unsaturated carbon chain of Ci
  • Group is a halogen atom, Ci-C 8 alkyl group, Ci-C 8 alkoxy groups, Ci-C 4 C port alkyl group, phenyl group, phenoxy group, N0 2, CN, C02- ( Ci-C4 alkyl Le) group, SCH 3 , N (CH 3 ) 2 or (optionally selected from 0 2 CH 3 ;;), C 3 -C 8 alkenyl group, -QN (R8) -substituted phenyl group (Q is Ci-C It represents 6 which may be branched saturated or unsaturated carbon chain of the substituents phenyl groups are selected from hydrogen atom, halogen atom, Ci-C 6 alkyl group, a Ci-C 6 alkoxy group optionally, R8 is was or hydrogen atom represents a Ci-C 4 alkyl group.), C 3 -C 8 haloalkynyl group or
  • R4 and R5 each independently represent a saturated or unsaturated Ci-C 6 alkyl group which may be branched
  • R6 and R7 each independently represent a> _logen atom
  • Ci - C 4 haloalkyl group Ci-C 4 haloalkoxy group
  • R1 and R2 may form a 3- to 8-membered ring which may contain a carbon atom, an oxygen atom, a hydrogen atom, a sulfur atom and a nitrogen atom.
  • R3 is Ci -Cio alkyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 cycloalkyl (C1 -C4) alkyl group, C 3 -C 6 halocycloalkyl group, Ci -C 4 alkyl (C 3 -C 8) cycloalkyl group, C 3 -Cio Arukeninore group, Ci -C 6 haloalkyl group, C 3 -Ci 0 alkynyl, Ci -C 2 scan Ruhoniru (Ci -C4) alkyl, Ci -C 6 alkoxy ( Represents a C 6 -C 6 ) alkynole group or a d -C 4 alkylthio (C 3 -C 6) cycloalkynole group.
  • the salts thereof (however, when these compounds have optical isomers, diastereomers, and geometric isomers, the respective mixtures and the
  • the compounds of the present invention also exhibit excellent insecticidal activity in addition to bactericidal activity.
  • insecticide having such a chemical structure has been known at all, and the compound of the present invention is very useful as a novel insecticide.
  • the compound of the present invention exhibits excellent microbicidal activity and can be used as a bactericidal biocide in plant protection and substance storage. It has preventive, curative or systemic control effects on many plant diseases.
  • the plant diseases targeted by the compound of the present invention include rice blast
  • ampelopsidis ⁇ Anthracnose of iki (Gloeosporium kaki), Pest control (Cercospora kaki. Mvcos Dhaerella nawae), Pest rot (Pseudoperenospora cubensis), Anthracnose (Colletotrichum lagenarium), Sickness (Sphaerotheca) fuliginea), vine blight ⁇ Mycosphaerella melonis), Tomato epidemic 3Ph (Phvtophthora infestans), Leaf blight (Fusarium oxvsporum), Ring blight (Alternaria solani), Leaf blight (Cladosoorium fulvam), Eggplant Disease (Phomopsis vexans), powdery mildew (ErysiDhe
  • White scab (Elsinoe leucospila), Tobacco scab (Alternaria lon3 ⁇ 4 pes), Powdery mildew (Ervsiphe cichoracearum), Anthracnose (Colletotrichum tabacum), Tensai scab (Cercospora beticola), , Scab of Diqlocarpon rosae, powdery mildew (Sphaerotheca pannosa), plum blight of chrysanthemum (Septoria
  • chrvsanthemiindici white rust (Puccinia horiana), vent-class Fraun notch (Phizoctonia solani), biscumber blight MPythium spp.), tara spot (Sclerotinia homoeocarpa ⁇ ., and each snow rot (Typhula spp, Fusarium nivale,
  • sorokinianum H. ervthrospilum
  • Noshiba various rice vegetation diseases
  • P. graminicol P. vanterpoolii
  • leaf rot lhizoctonia solani gray mold on various crops
  • Botrvtis cinerea sclerotium (clerotinia sclerotiorum), etc.
  • the compound of the present invention can be used as an active ingredient of a fungicide for agricultural and horticultural use in fields, paddy fields, turf, orchards, pastures, greenhouses and other non-cultivated lands.
  • the compound of the present invention is effective against various harmful insects at a low drug concentration.
  • the insect pests include, for example, black-tailed maggots, flying beetles, peach aphids, mosquito aphids, mosquitos, tossed mosses, kobunomeiga, konaga, kotoga, montoshirocho, ikiburaga, cyanokokakumonhamaki, tobacco, tobacco, tobacco Agricultural pests such as Chinese bite corn cone bollers, fall army worms, corn worms, southern corn root worms, northern corn root worms, western corn root worms; Sanitary pests such as power, housefly, house cockroach, cockroach, flea, flea, lice, etc., grain storage pests, such as bollworms, skulls, pests, house pests, such as termites, danii, fleas, lice, etc.
  • the compounds of the present invention can effectively control pests of Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Termites and Mite and Lice at low concentrations.
  • the compounds of the present invention exhibit excellent effects as fungicides and insecticides.
  • the compound of the present invention can be synthesized, for example, by the methods shown in Schemes 1 to 3. OO
  • the synthetic route (VI ⁇ Vm ⁇ IX) is to react the alcohol (VI) with an appropriate halogenating agent, such as phosphorus oxychloride, 5-phosphorous chloride, thionyl chloride, concentrated hydrochloric acid, etc., to form the corresponding halogen compound (VIII). Is shown. A method for producing a compound (IX) by reacting VIII with a nucleophile Nu: will be described.
  • Table 2-1 shows the compounds of the present invention synthesized according to the above schemes or examples, including the compounds synthesized in the above examples, but the present invention is not limited thereto.
  • NHCH 2 1 4 Me— Ph eny l NHCH a -4-Et-Ph eny 1 NHCH 2-4 -P r n 1 Ph eny 1 NHCH 2-4 -P r iso 1 Ph eny l NHCH 2 --Bu n -Ph eny 1 NHCH 2-4 -Bu sec -Ph eny] NHCH 2-4 1 Bu is .
  • Ph eny ⁇ NHCH 2 -4 -Bu tert -P heny 1 NHCH 2 --Me 0-P heny 1 NHCH 2 one 4— EtO— Ph eny 1 NHCH 2 one four one Pr is ° ⁇ ⁇ Ph eny l NHCH 2 --P r n OP h eny 1 NHCH 2 -4 -Bu n ⁇ 1 Ph eny 1 NHCH 2-4 -Bu sec OP heny 1 NHCH a- 1 4-1 Bu is ° ⁇ 1 Ph eny l NHCH 2 -4- Bu tert OP heny 1 R 1 1 ( N (R 1) R 2)
  • N (Me) CH (Me) -4 -P r is .
  • ⁇ - Ph eny IN (Me) CH ( Me) one 4- P r n OP heny 1 N (e) CH (Me) - -B u n OP heny 1 N (Me) CH (Me) - one B u sec OP he ⁇ y 1 N (Me) CH (Me) 1 4 1 Bu is ° ⁇ —P he Ti y] N (Me) CH (Me)-4 -B u tert ⁇ 1 P heny ⁇ N (Me) CH (Me) 1 4 1 CF 3 -Ph eny l
  • NHCH a CH 0-2, 6 -C 1 2 -4 -CF 3 -P henyl NHCH2 CH 2 0-2 -F-4. 6 -C 1 2 -P henyl NHCH a CH 2 0-2, 3, 4. 5, 6 -F 5 -Pheny 1 NHCH 2 CH 2 CH 2 1 2— F— P heny l
  • NHCH 2 one (2 C 1 - 6 one P H_ ⁇ one P he ⁇ y 1)
  • NHCH 2 one (3 (e) 2 NP he ⁇ y 1)
  • NHCH 2 - (4 P h CH 2 0- P heny 1)
  • NHCH 2 CH 2 (2 -B r -P heny 1)
  • NHCH 2 CH 2 (3-B r-Ph eny 1)
  • NHCH (Me)-(3 -Et OP heny 1) NHCH (Me)-(2 -iso -Pr OP hen 1) NHCH (Me)-(3 -iso -Pr OP hen y.1) NHCH ( Me) Ichi (2 -Pr OP heny 1) NHCH (Me) Ichi (3 -Pr OP heny 1) NHCH (Me) Ichi (2 -BuO-P heny 1) NHCH (Me)-(3 -BuO- P heny 1) NHCH (Me)-(2-sec -BuO-P heny 1) NHCH (Me) ichi (3 -sec -BuO-P heny 1) NHCH (Me) ⁇ (2 -iso -BuO-P heny 1) NHCH (Me) 1 (3—iso — BuO—Pheny l) NHCH (e) 1 (2 -tert-Bu
  • NHC (e) 2 one (2, 6 -C 1 a -P heny 1) NHC (e) 2 one (3, -C 12 -P heny 1 ) NHC (e) a one (3, 5- C 1 2 -P henyl) NHC (e) 2 - (2, 3 -F 2 -P heny 1 NHC (Me) 2 one (2, 4 -F 2 -Ph enyl NHC (Me) 2 one (2, 5- F 2 -P heny 1 NHC (e) 2-(2, 6 -F 2 -P he Ti y 1 NHC (Me) 2 I (3, 4 -F 2 I Ph eny 1 NHC (Me) 2 I (3, 5 — F a i Ph phenyl NHCH (E t) P h

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  • 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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Bactéricide et insecticide comprenant, en tant qu'ingrédient actif, un composé de formule générale (I), dans laquelle X est chloro, etc.; R1 est hydrogène, alkyle C¿1-6?, etc.; R?2¿ est hydrogène, alkyle C¿1-6?, phényle éventuellement substitué, etc. ou R?1 et R2¿ peuvent former ensemble un cycle de 3 à 8 éléments contenant éventuellement carbone, oxygène, hydrogène, soufre et azote; et R3 représente alkyle C¿1-8?, cycloalkyle C3-6, etc.
PCT/JP1996/000129 1995-01-27 1996-01-25 Nouveaux derives de pyrimidine, bactericide et insecticide WO1996022980A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU44960/96A AU4496096A (en) 1995-01-27 1996-01-25 Novel pyrimidine derivatives, bactericide and insecticide

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP1189495 1995-01-27
JP7/11894 1995-01-27
JP22813095 1995-09-05
JP7/228130 1995-09-05
JP8/4039 1996-01-12
JP403996A JPH11228545A (ja) 1995-01-27 1996-01-12 新規ピリミジン誘導体及び殺菌、殺虫剤

Publications (1)

Publication Number Publication Date
WO1996022980A1 true WO1996022980A1 (fr) 1996-08-01

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Application Number Title Priority Date Filing Date
PCT/JP1996/000129 WO1996022980A1 (fr) 1995-01-27 1996-01-25 Nouveaux derives de pyrimidine, bactericide et insecticide

Country Status (3)

Country Link
JP (1) JPH11228545A (fr)
AU (1) AU4496096A (fr)
WO (1) WO1996022980A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999044997A1 (fr) * 1998-03-06 1999-09-10 Ube Industries, Ltd. 6-(α-FLUOROALKYL)-4-PYRIMIDONES ET LEUR PROCEDE DE PRODUCTION
WO2001017975A1 (fr) * 1999-09-09 2001-03-15 Kumiai Chemical Industry Co., Ltd. Derives de pyrimidine et herbicides les contenant

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0632784A (ja) * 1992-05-15 1994-02-08 Hoechst Ag ４−アルキル−置換ピリミジン−５−カルボキシアニリド、それらの製造方法、それらを含有する組成物およびそれらの殺菌剤としての用途
WO1995012582A1 (fr) * 1993-11-01 1995-05-11 Nissan Chemical Industries, Ltd. Nouveau derive de pyrimidine disubstitue en positions 4 et 5 et herbicide

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0632784A (ja) * 1992-05-15 1994-02-08 Hoechst Ag ４−アルキル−置換ピリミジン−５−カルボキシアニリド、それらの製造方法、それらを含有する組成物およびそれらの殺菌剤としての用途
WO1995012582A1 (fr) * 1993-11-01 1995-05-11 Nissan Chemical Industries, Ltd. Nouveau derive de pyrimidine disubstitue en positions 4 et 5 et herbicide

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999044997A1 (fr) * 1998-03-06 1999-09-10 Ube Industries, Ltd. 6-(α-FLUOROALKYL)-4-PYRIMIDONES ET LEUR PROCEDE DE PRODUCTION
US6340757B1 (en) 1998-03-06 2002-01-22 Ube Industries, Ltd. 6-(1-fluoroalkyl)-4-pyrimidones and processes for producing the same
WO2001017975A1 (fr) * 1999-09-09 2001-03-15 Kumiai Chemical Industry Co., Ltd. Derives de pyrimidine et herbicides les contenant
EP1211246A1 (fr) * 1999-09-09 2002-06-05 Kumiai Chemical Industry Co., Ltd. Derives de pyrimidine et herbicides les contenant
EP1211246A4 (fr) * 1999-09-09 2002-10-09 Kumiai Chemical Industry Co Derives de pyrimidine et herbicides les contenant
US6806230B1 (en) 1999-09-09 2004-10-19 Kumiai Chemical Industry Co., Ltd. Pyrimidine derivatives and herbicides containing them
JP4703077B2 (ja) * 1999-09-09 2011-06-15 クミアイ化学工業株式会社 ピリミジン誘導体及びそれを含有する除草剤

Also Published As

Publication number Publication date
AU4496096A (en) 1996-08-14
JPH11228545A (ja) 1999-08-24

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