CA1053148A - Derives de n-3 phenylcarbamoyl hydroxy-4 coumarin comme insecticides - Google Patents

Derives de n-3 phenylcarbamoyl hydroxy-4 coumarin comme insecticides

Info

Publication number: CA1053148A
Authority: CA; Canada
Prior art keywords: parts; active substance; compound; formula; phenylcarbamoyl
Prior art date: 1975-09-29
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

CA262,082A

Other languages

English (en)

Inventor

Ernst Beriger

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.)

Novartis AG

Original Assignee

Ciba Geigy AG

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.)

1975-09-29

Filing date

1976-09-27

Publication date

1979-04-24

1975-09-29 Priority claimed from CH1258975A external-priority patent/CH617569A5/de

1975-09-29 Priority claimed from CH1259075A external-priority patent/CH617319A5/de

1976-09-27 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1979-04-24 Application granted granted Critical

1979-04-24 Publication of CA1053148A publication Critical patent/CA1053148A/fr

Status Expired legal-status Critical Current

Links

241000238631 Hexapoda Species 0.000 title claims abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 16
241000607479 Yersinia pestis Species 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 10
229920000742 Cotton Polymers 0.000 claims description 2
235000013311 vegetables Nutrition 0.000 claims description 2
239000013543 active substance Substances 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
238000012360 testing method Methods 0.000 description 11
239000000203 mixture Substances 0.000 description 9
239000000126 substance Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000008187 granular material Substances 0.000 description 6
241000196324 Embryophyta Species 0.000 description 5
241000258916 Leptinotarsa decemlineata Species 0.000 description 5
229940125782 compound 2 Drugs 0.000 description 5
239000000758 substrate Substances 0.000 description 5
-1 triethylamine Chemical class 0.000 description 5
VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical compound C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 description 4
239000005995 Aluminium silicate Substances 0.000 description 4
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
241000736227 Lucilia sericata Species 0.000 description 4
241000257159 Musca domestica Species 0.000 description 4
244000061456 Solanum tuberosum Species 0.000 description 4
235000012211 aluminium silicate Nutrition 0.000 description 4
239000000969 carrier Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
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 4
239000002904 solvent Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
230000000749 insecticidal effect Effects 0.000 description 3
235000015097 nutrients Nutrition 0.000 description 3
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
238000005507 spraying Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 2
241000254173 Coleoptera Species 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
235000019993 champagne Nutrition 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
229920005610 lignin Polymers 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
QFBDCSDDHUBEGG-UHFFFAOYSA-N 1,2-dibutylnaphthalene;sodium Chemical compound [Na].C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 QFBDCSDDHUBEGG-UHFFFAOYSA-N 0.000 description 1
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
BKVXLJAGUKAXTN-UHFFFAOYSA-N 4-chlorobenzoyl azide Chemical compound ClC1=CC=C(C(=O)N=[N+]=[N-])C=C1 BKVXLJAGUKAXTN-UHFFFAOYSA-N 0.000 description 1
241000256111 Aedes <genus> Species 0.000 description 1
241000256118 Aedes aegypti Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
241000255925 Diptera Species 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
240000002024 Gossypium herbaceum Species 0.000 description 1
235000004341 Gossypium herbaceum Nutrition 0.000 description 1
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 1
239000005909 Kieselgur Substances 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
101100172132 Mus musculus Eif3a gene Proteins 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
241000256250 Spodoptera littoralis Species 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229940115440 aluminum sodium silicate Drugs 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000000507 anthelmentic effect Effects 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229960000956 coumarin Drugs 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000000266 injurious effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
230000029052 metamorphosis Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000000429 sodium aluminium silicate Substances 0.000 description 1
235000012217 sodium aluminium silicate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/56—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 without hydrogen atoms in position 3
- 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
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA262,082A 1975-09-29 1976-09-27 Derives de n-3 phenylcarbamoyl hydroxy-4 coumarin comme insecticides Expired CA1053148A (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
CH1258975A CH617569A5 (en)	1975-09-29	1975-09-29	Pesticides containing, as active ingredient, a 3-N-phenyl-carbamoyl-4-hydroxy-1,2-(benzo)pyrone derivative.
CH1259075A CH617319A5 (en)	1975-09-29	1975-09-29	Use of 3-N-phenylcarbamoyl-4-hydroxycoumarin derivatives for controlling insects.
CH512976		1976-04-23
CH513076		1976-04-23
CH577476		1976-05-06
CH789076		1976-06-21

Publications (1)

Publication Number	Publication Date
CA1053148A true CA1053148A (fr)	1979-04-24

Family

ID=27543763

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA262,082A Expired CA1053148A (fr)	1975-09-29	1976-09-27	Derives de n-3 phenylcarbamoyl hydroxy-4 coumarin comme insecticides

Country Status (6)

Country	Link
JP (1)	JPS5244236A (fr)
CA (1)	CA1053148A (fr)
DE (1)	DE2643428A1 (fr)
FR (1)	FR2325324A1 (fr)
GB (1)	GB1536295A (fr)
IL (1)	IL50558A (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5999351A (ja) *	1982-11-30	1984-06-08	Shimadzu Corp	不活性ガス中の微量酸素の分析方法
DE3586542T2 (de) *	1985-08-06	1993-04-08	Earth Chemical Co	Akarizide.
ES2077867T3 (es) *	1990-09-28	1995-12-01	Upjohn Co	3-carbamoil-4-hidroxicumarinas antihelminticas y anticoccidiales, procedimiento de uso y composiciones.
US5624951A (en) *	1992-09-01	1997-04-29	Pfizer Inc.	4-hydroxy coumarin derivatives with antibacterial activity
US5985912A (en) *	1996-12-20	1999-11-16	Pfizer Inc.	4-hydroxy coumarin derivatives

1976
- 1976-09-22 FR FR7628489A patent/FR2325324A1/fr active Granted
- 1976-09-27 CA CA262,082A patent/CA1053148A/fr not_active Expired
- 1976-09-27 DE DE19762643428 patent/DE2643428A1/de not_active Withdrawn
- 1976-09-28 GB GB40214/76A patent/GB1536295A/en not_active Expired
- 1976-09-28 IL IL50558A patent/IL50558A/xx unknown
- 1976-09-29 JP JP51117065A patent/JPS5244236A/ja active Pending

Also Published As

Publication number	Publication date
FR2325324A1 (fr)	1977-04-22
GB1536295A (en)	1978-12-20
JPS5244236A (en)	1977-04-07
DE2643428A1 (de)	1977-04-07
FR2325324B1 (fr)	1979-09-28
IL50558A0 (en)	1976-11-30
IL50558A (en)	1979-11-30

Publication	Publication Date	Title
US4162330A (en)	1979-07-24	Acylurea insecticides
DE2418295A1 (de)	1974-11-07	Diphenylaether, verfahren zu ihrer herstellung und ihre verwendung
US4262020A (en)	1981-04-14	Acylurea insecticides
US4342778A (en)	1982-08-03	Insecticidal (2,3-dihydro-2,2-dimethylbenzofuran-7-yloxy-N-methylcarbamoyl)-(N'-alkoxycarbamoyl)-sulphides
US4310548A (en)	1982-01-12	Pesticidal N-tetrafluorophenyl-N'-benzoyl ureas
US4229454A (en)	1980-10-21	Insecticidal 5-phenylcarbamoyl-barbituric acid
US4321276A (en)	1982-03-23	Phenylureas
CA1053148A (fr)	1979-04-24	Derives de n-3 phenylcarbamoyl hydroxy-4 coumarin comme insecticides
CA1088079A (fr)	1980-10-21	Derives de 3-n-phenyl-carbamoyl-4-hydroxy-1,2-(benzo)- pyrone a activite insecticide
US4418066A (en)	1983-11-29	Phenylbenzoylureas
US4078075A (en)	1978-03-07	Insecticidally active 3-N-(4-trifluoromethylphenyl)-carbamoyl-4-hydroxy-coumarin
CA1074316A (fr)	1980-03-25	Acides 5-phenylcarbamoyl-barbituriques
DE2516382A1 (de)	1975-11-06	Phenyl-aralkyl-aether, -thioaether und -amine
US4123551A (en)	1978-10-31	2,2-Disubstituted-phenylcarbamoyl-6-hydroxy-m-dioxin-4-one derivatives having insecticidal properties
JPS6293268A (ja)	1987-04-28	置換ｎ−ベンゾイル−ｎ′−３，５−ジクロロ−４−ヘキサフルオロプロピルオキシフエニル尿素及びその製造方法
US4339460A (en)	1982-07-13	Pesticidal N-[4-(3'-bromoallyloxy)-phenyl]-N'-benzoyl ureas
US4073932A (en)	1978-02-14	Method of controlling insects using 1,3-dioxin-4-ones
US4072752A (en)	1978-02-07	Pesticidal benzaspiro carboxylates
US4560770A (en)	1985-12-24	Pesticidal compositions based on N-pyrrolylphenyl-N'-benzoylurea compounds
CA1139784A (fr)	1983-01-18	Phenylurees
GB1579635A (en)	1980-11-19	Sulphenamides and their use in pesticidal compositions
GB1600803A (en)	1981-10-21	Furylmethyloxime ethers and pesticidal compositions containing them
CH643563A5 (en)	1984-06-15	1,3-Diaza-2-phosphacyclohexane derivatives
DE3133009A1 (de)	1982-04-08	N-pyridinyl-n'-benzoylharnstoffe
DE2616755A1 (de)	1976-10-28	Diaether, verfahren zu ihrer herstellung und ihre verwendung