CA1204784A - Derives de substitution de benzylcycloalcenyluree; methode de preparation; utilisation comme fongicides en agriculture et en horticulture - Google Patents

Derives de substitution de benzylcycloalcenyluree; methode de preparation; utilisation comme fongicides en agriculture et en horticulture

Info

Publication number: CA1204784A
Authority: CA; Canada
Prior art keywords: formula; compound; cyclohexen; butyl; substituted benzyl
Prior art date: 1982-12-03
Legal status (The legal status 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 status listed.): Expired

Application number

CA000479655A

Other languages

English (en)

Inventor

Yasuo Yamada

Junichi Saito

Tatsuo Tamura

Shinji Sakawa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer CropScience KK

Original Assignee

Nihon Tokushu Noyaku Seizo 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.)

1982-12-03

Filing date

1985-04-19

Publication date

1986-05-20

1982-12-03 Priority claimed from JP57211241A external-priority patent/JPS59101443A/ja

1985-04-19 Application filed by Nihon Tokushu Noyaku Seizo KK filed Critical Nihon Tokushu Noyaku Seizo KK

1985-04-19 Priority to CA000479655A priority Critical patent/CA1204784A/fr

1986-05-20 Application granted granted Critical

1986-05-20 Publication of CA1204784A publication Critical patent/CA1204784A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 41
239000000417 fungicide Substances 0.000 title abstract description 10
239000000543 intermediate Substances 0.000 title abstract description 6
238000002360 preparation method Methods 0.000 title description 21
238000003898 horticulture Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 64
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
125000005843 halogen group Chemical group 0.000 claims abstract description 10
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 7
238000004519 manufacturing process Methods 0.000 claims abstract description 5
-1 sec.-butyl Chemical group 0.000 claims description 51
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000001309 chloro group Chemical group Cl* 0.000 claims description 14
239000007858 starting material Substances 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 8
239000011230 binding agent Substances 0.000 claims description 7
239000000460 chlorine Chemical group 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
238000009835 boiling Methods 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
DYQXLNFFXFNAOA-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]cyclohex-2-en-1-amine Chemical compound C1=CC(Cl)=CC=C1CNC1C=CCCC1 DYQXLNFFXFNAOA-UHFFFAOYSA-N 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
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QDXGHDGUSWHPKM-UHFFFAOYSA-N n-[(4-bromophenyl)methyl]cyclohex-2-en-1-amine Chemical compound C1=CC(Br)=CC=C1CNC1C=CCCC1 QDXGHDGUSWHPKM-UHFFFAOYSA-N 0.000 claims description 2
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UFKSTOGBFHOXER-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]cyclohex-2-en-1-amine Chemical compound C1=CC(C)=CC=C1CNC1C=CCCC1 UFKSTOGBFHOXER-UHFFFAOYSA-N 0.000 claims description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 2
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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125000001246 bromo group Chemical group Br* 0.000 description 8
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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230000001488 breeding effect Effects 0.000 description 6
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238000001816 cooling Methods 0.000 description 6
239000008187 granular material Substances 0.000 description 6
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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230000001276 controlling effect Effects 0.000 description 5
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000945 filler Substances 0.000 description 4
230000000855 fungicidal effect Effects 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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241001617088 Thanatephorus sasakii Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
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125000000753 cycloalkyl group Chemical group 0.000 description 3
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 3
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BIOZOXVVHYZFIH-UHFFFAOYSA-N n-[(4-bromophenyl)methyl]-n-cyclopent-2-en-1-ylcarbamoyl chloride Chemical compound C1CC=CC1N(C(=O)Cl)CC1=CC=C(Br)C=C1 BIOZOXVVHYZFIH-UHFFFAOYSA-N 0.000 description 3
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239000011734 sodium Substances 0.000 description 3
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 2
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235000019333 sodium laurylsulphate Nutrition 0.000 description 1
YFGAFXCSLUUJRG-WCCKRBBISA-M sodium;(2s)-2-amino-5-(diaminomethylideneamino)pentanoate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCCN=C(N)N YFGAFXCSLUUJRG-WCCKRBBISA-M 0.000 description 1
241000894007 species Species 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
229960002415 trichloroethylene Drugs 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
235000015099 wheat brans Nutrition 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000479655A 1982-12-03 1985-04-19 Derives de substitution de benzylcycloalcenyluree; methode de preparation; utilisation comme fongicides en agriculture et en horticulture Expired CA1204784A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000479655A CA1204784A (fr)	1982-12-03	1985-04-19	Derives de substitution de benzylcycloalcenyluree; methode de preparation; utilisation comme fongicides en agriculture et en horticulture

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP57211241A JPS59101443A (ja)	1982-12-03	1982-12-03	置換ベンジルシクロアルケニルウレア誘導体その製法及び農園芸用殺菌剤
JP57-211241		1982-12-03
CA000442342A CA1203249A (fr)	1982-12-03	1983-12-01	Derives substitues de la benzyl-cycloalkenyl uree leurs intermediaires, les procedes utilises pour leur preparation et utilisation comme fongicides en agriculture et en horticulture
CA000479655A CA1204784A (fr)	1982-12-03	1985-04-19	Derives de substitution de benzylcycloalcenyluree; methode de preparation; utilisation comme fongicides en agriculture et en horticulture

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000442342A Division CA1203249A (fr)	1982-12-03	1983-12-01	Derives substitues de la benzyl-cycloalkenyl uree leurs intermediaires, les procedes utilises pour leur preparation et utilisation comme fongicides en agriculture et en horticulture

Publications (1)

Publication Number	Publication Date
CA1204784A true CA1204784A (fr)	1986-05-20

Family

ID=25670229

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000479655A Expired CA1204784A (fr)	1982-12-03	1985-04-19	Derives de substitution de benzylcycloalcenyluree; methode de preparation; utilisation comme fongicides en agriculture et en horticulture

Country Status (1)

Country	Link
CA (1)	CA1204784A (fr)

1985
- 1985-04-19 CA CA000479655A patent/CA1204784A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2003-12-01	MKEX	Expiry

Publication	Publication Date	Title
JPH03120265A (ja)	1991-05-22	５ｈ―フラン―２―オン誘導体
JP2007031395A (ja)	2007-02-08	殺虫性３−アシルアミノベンズアニリド類
RU2535674C2 (ru)	2014-12-20	Новые иминопроизводные, способы их получения и инсектициды, содержащие такие иминопроизводные
JP3159859B2 (ja)	2001-04-23	殺虫性ニトロ化合物
CA1203249A (fr)	1986-04-15	Derives substitues de la benzyl-cycloalkenyl uree leurs intermediaires, les procedes utilises pour leur preparation et utilisation comme fongicides en agriculture et en horticulture
JP2009516647A (ja)	2009-04-23	殺虫性２−アシルアミノチアゾール−４−カルボキサミド類
PL130861B1 (en)	1984-09-29	Herbicide and method of manufacture of novel substituted derivatives of phenylsulfonylurea
CA1204784A (fr)	1986-05-20	Derives de substitution de benzylcycloalcenyluree; methode de preparation; utilisation comme fongicides en agriculture et en horticulture
US5237100A (en)	1993-08-17	Substituted benzylcycloalkenylamines and carbamoylhalide intermediates therefor
CA1166250A (fr)	1984-04-24	Derives substitues de la tetrahydropyrimidinone, procede de preparation et utilisation comme herbicides
HU207039B (en)	1993-03-01	Process for producing anilinophenyl thiourea, -isothiourea and -carbodiimide derivatives, as well as compositions for exterminating insect and acarus pests of plants comprising such compounds as active ingredient and their application
US4906650A (en)	1990-03-06	N-sulphenylated 2-amino-4-chloro-thiazole-sulphonamides, their use, process for their preparation, and the intermediates 2,4-dichlorothiazole-sulphonyl chloride and 2-amino-4-chloro-thiazole-sulphonamides
CA1180334A (fr)	1985-01-02	Biurets sulfenyles en n; preparation et emploi comme fongicides
JPS6160665A (ja)	1986-03-28	１‐（２‐トリフルオルメトキシ‐フエニルスルホニル）‐３‐ヘテロアリール尿素又はチオ尿素類
US4564638A (en)	1986-01-14	Fungicidal novel N-benzyl-N-(2-norbornyl)-ureas
CA1185989A (fr)	1985-04-23	Urees n-sulfenylees; preparation fongicides qui en renferment, et utilisation
CA1181067A (fr)	1985-01-15	Methode de preparation de 1-amino-1,3,5-triazine-2,4 (1h, 3h)-diones
EP0250744A2 (fr)	1988-01-07	Dérivés de cyanoacétamide à activité fongicide
US5721192A (en)	1998-02-24	Aminosulfonyl ureas
US4581365A (en)	1986-04-08	Trichloroacryloyl oxime fungicides
JPH0149344B2 (fr)	1989-10-24
US3996275A (en)	1976-12-07	Dithiocarbamate hydrochloride salts and their manufacture
JPS58140078A (ja)	1983-08-19	メチル置換テトラヒドロ−２−ピリミジノン誘導体、その製法、その中間体及び該中間体の製法、並びに除草剤
KR820000055B1 (ko)	1982-02-06	우레아 또는 티오우레아 화합물의 제조방법
KR820000176B1 (ko)	1982-02-24	우레아 유도체의 제조 방법