BG62196B1 - Нови тетразинови производни с акарицидна активност - Google Patents

Нови тетразинови производни с акарицидна активност Download PDF

Info

Publication number: BG62196B1
Authority: BG; Bulgaria
Prior art keywords: formula; tetrazine; hydrazine; eggs; difluorophenyl
Prior art date: 1993-07-21

Application number

BG98920A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG98920A (en

Inventor

Janis Hajimichel

Sandor Botar

Edit Bleicher

Laszlo Pap

Istvan Szekely

Katalin Marmarosi Geb. Kellner

Janos Oeri

Original Assignee

Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.

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.)

1993-07-21

Filing date

1994-07-20

Publication date

1999-05-31

1994-07-20 Application filed by Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. filed Critical Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.

1995-03-31 Publication of BG98920A publication Critical patent/BG98920A/bg

1999-05-31 Publication of BG62196B1 publication Critical patent/BG62196B1/bg

Links

150000004905 tetrazines Chemical class 0.000 title claims abstract description 9
230000000895 acaricidal effect Effects 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims abstract description 49
238000002360 preparation method Methods 0.000 claims abstract description 16
238000000034 method Methods 0.000 claims abstract description 10
230000000694 effects Effects 0.000 claims abstract description 8
230000003151 ovacidal effect Effects 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
230000000974 larvacidal effect Effects 0.000 claims abstract 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 41
235000013601 eggs Nutrition 0.000 claims description 24
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 20
125000001246 bromo group Chemical group Br* 0.000 claims description 19
-1 3,6-disubstituted-1,2,4,5-tetrazine Chemical class 0.000 claims description 18
241000238876 Acari Species 0.000 claims description 18
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 10
239000004094 surface-active agent Substances 0.000 claims description 6
231100000194 ovacidal Toxicity 0.000 claims description 5
KHAZAQVGODYYJZ-UHFFFAOYSA-N 3-(2-bromophenyl)-6-(2,6-difluorophenyl)-1,2,4,5-tetrazine Chemical compound FC1=CC=CC(F)=C1C1=NN=C(C=2C(=CC=CC=2)Br)N=N1 KHAZAQVGODYYJZ-UHFFFAOYSA-N 0.000 claims description 3
SWBHWUYHHJCADA-UHFFFAOYSA-N 3-(2-chlorophenyl)-6-(2,6-difluorophenyl)-1,2,4,5-tetrazine Chemical compound FC1=CC=CC(F)=C1C1=NN=C(C=2C(=CC=CC=2)Cl)N=N1 SWBHWUYHHJCADA-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
ITQQWDCXHUCUSJ-UHFFFAOYSA-N 3,6-bis(2,6-difluorophenyl)-1,2,4,5-tetrazine Chemical compound FC1=CC=CC(F)=C1C1=NN=C(C=2C(=CC=CC=2F)F)N=N1 ITQQWDCXHUCUSJ-UHFFFAOYSA-N 0.000 claims description 2
150000008051 alkyl sulfates Chemical class 0.000 claims description 2
150000004891 diazines Chemical class 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
239000000945 filler Substances 0.000 claims 1
239000000460 chlorine Substances 0.000 abstract description 8
229910052801 chlorine Inorganic materials 0.000 abstract description 2
229910052731 fluorine Inorganic materials 0.000 abstract description 2
241000934067 Acarus Species 0.000 abstract 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
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238000005160 1H NMR spectroscopy Methods 0.000 description 4
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239000012085 test solution Substances 0.000 description 4
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238000004440 column chromatography Methods 0.000 description 3
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JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 3
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OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
235000013305 food Nutrition 0.000 description 1
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
238000007654 immersion Methods 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
235000009973 maize Nutrition 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
RDGDYWZFJRKWQR-UHFFFAOYSA-N n,n-diethylethanamine;2,3-dihydroxybutanedioic acid Chemical compound CCN(CC)CC.OC(=O)C(O)C(O)C(O)=O RDGDYWZFJRKWQR-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
244000045947 parasite Species 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
244000062645 predators Species 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
238000011160 research Methods 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
235000021012 strawberries Nutrition 0.000 description 1
230000001502 supplementing effect Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
230000005945 translocation Effects 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/08—Six-membered rings
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

BG98920A 1993-07-21 1994-07-20 Нови тетразинови производни с акарицидна активност BG62196B1 (bg)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU9302098A HU212613B (en)	1993-07-21	1993-07-21	Tetrazine-derivatives, process for production of the compounds, acaricidal,larvicidal and ovicidal compositions containing the compounds as active ingredient and process for their production and their use

Publications (2)

Publication Number	Publication Date
BG98920A BG98920A (en)	1995-03-31
BG62196B1 true BG62196B1 (bg)	1999-05-31

Family

ID=10983812

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG98920A BG62196B1 (bg)	1993-07-21	1994-07-20	Нови тетразинови производни с акарицидна активност

Country Status (28)

Country	Link
US (2)	US5455237A (pt)
EP (1)	EP0635499B1 (pt)
JP (1)	JP3662952B2 (pt)
KR (1)	KR100373689B1 (pt)
CN (1)	CN1066722C (pt)
AT (1)	ATE177087T1 (pt)
AU (1)	AU682366B2 (pt)
BG (1)	BG62196B1 (pt)
BR (2)	BR9402868A (pt)
CA (1)	CA2128378C (pt)
CZ (1)	CZ286600B6 (pt)
DE (1)	DE69416739T2 (pt)
DK (1)	DK0635499T3 (pt)
DZ (1)	DZ1801A1 (pt)
EG (1)	EG20427A (pt)
ES (1)	ES2130312T3 (pt)
GR (1)	GR3029999T3 (pt)
HU (1)	HU212613B (pt)
LV (1)	LV10950B (pt)
MA (1)	MA23274A1 (pt)
MY (1)	MY111282A (pt)
PL (1)	PL178152B1 (pt)
RO (1)	RO113988B1 (pt)
RU (1)	RU2142949C1 (pt)
SK (1)	SK281778B6 (pt)
TW (1)	TW326386B (pt)
UA (1)	UA27871C2 (pt)
ZA (1)	ZA945345B (pt)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU212613B (en) *	1993-07-21	1996-09-30	Chinoin Gyogyszer Es Vegyeszet	Tetrazine-derivatives, process for production of the compounds, acaricidal,larvicidal and ovicidal compositions containing the compounds as active ingredient and process for their production and their use
CO5160333A1 (es) *	1999-06-21	2002-05-30	Novartis Ag	Derivados de tetrazina pesticidamente activos y composicion que los contine
US6458227B1 (en) *	2000-04-28	2002-10-01	The Regents Of The University Of California	Propellant containing 3;6-BIS(1H-1,2,3,4-Tetrazol-5-ylamino)-1,2,4,5-tetrazine or salts thereof
DE102007045922A1 (de)	2007-09-26	2009-04-02	Bayer Cropscience Ag	Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
CN105104407B (zh) *	2012-03-10	2017-06-16	陕西韦尔奇作物保护有限公司	一种高效杀虫组合物
CN103300020B (zh) *	2012-03-12	2016-06-08	陕西韦尔奇作物保护有限公司	一种农药组合物
CN105557707B (zh) *	2012-03-13	2018-04-03	陕西韦尔奇作物保护有限公司	一种含有氟螨嗪的杀虫组合物
CN102960353A (zh) *	2012-10-27	2013-03-13	海利尔药业集团股份有限公司	一种含有氰氟虫腙与氟螨嗪的杀虫杀螨组合物
CN103416409A (zh) *	2012-12-15	2013-12-04	海利尔药业集团股份有限公司	一种含有氟螨嗪与甲氧虫酰肼的杀虫组合物
CN103039467A (zh) *	2012-12-28	2013-04-17	海利尔药业集团股份有限公司	一种含有氟螨嗪与螺虫乙酯的杀虫组合物
CN103444726A (zh) *	2013-09-06	2013-12-18	刘波	一种含氟螨嗪的农药杀螨剂
CN103719145B (zh) *	2013-12-30	2016-03-30	青岛崂乡茶制品有限公司	一种茶树用杀虫剂
CN106305732B (zh) *	2015-06-18	2019-03-19	沈阳中化农药化工研发有限公司	一种含有氟螨嗪的杀虫杀螨组合物
CN105130962B (zh) *	2015-09-06	2017-09-26	浙江博仕达作物科技有限公司	一种四嗪吡唑类杀螨剂
CN105061399B (zh) *	2015-09-06	2017-03-22	青岛科技大学	一种含氟四嗪吡啶类化合物及其用途
CN105123710B (zh) *	2015-09-28	2017-11-10	陕西先农生物科技有限公司	一种含氟螨嗪的农药组合物及其制备方法
US20200262799A1 (en) *	2015-11-30	2020-08-20	Universite De Bourgogne	Process for preparing functionalized 1,2,4,5-tetrazine compounds
CN108863838A (zh) *	2018-06-09	2018-11-23	石家庄市绿丰化工有限公司	一种合成双(α:2-氯苯亚甲基)肼的方法
CN110965143B (zh) *	2019-12-17	2022-04-01	上海茂腾针织有限公司	一种具有抗菌除臭性能的纤维及其制备方法
CN114163392B (zh) *	2020-09-11	2024-03-12	江苏优嘉植物保护有限公司	一种四螨嗪的制备方法
JP2024516912A (ja)	2021-05-14	2024-04-17	シンジェンタクロッププロテクションアクチェンゲゼルシャフト	昆虫、ダニ目及び線虫有害生物の防除

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU498300A1 (ru) *	1973-11-27	1976-01-05	Институт Органической Химии Ан Украинской Сср	Способ получени производных 3,6-диарил-симм-тетразина
DE2963331D1 (en) *	1978-05-25	1982-09-02	Fbc Ltd	Acaricidal, larvicidal and ovicidal tetrazine derivatives and compositions, processes for their preparation and methods of using them
EP0029657A3 (en) *	1979-11-16	1981-08-26	Fbc Limited	Pesticidal tetrazines, their use and compositions, processes for their preparation and preparation intermediates
SU1292667A3 (ru) *	1979-11-20	1987-02-23	Физонз Лимитед (Фирма)	Способ получени замещенных тетразинов
ES2018817B3 (es) *	1986-06-05	1991-05-16	Shell Int Research	Derivados de tetrazina plaguicidas.
IL100574A0 (en) *	1991-01-09	1992-09-06	Ciba Geigy Ag	Acaricidal compositions
HU212613B (en) *	1993-07-21	1996-09-30	Chinoin Gyogyszer Es Vegyeszet	Tetrazine-derivatives, process for production of the compounds, acaricidal,larvicidal and ovicidal compositions containing the compounds as active ingredient and process for their production and their use

1993
- 1993-07-21 HU HU9302098A patent/HU212613B/hu not_active IP Right Cessation
1994
- 1994-07-15 SK SK858-94A patent/SK281778B6/sk unknown
- 1994-07-15 CZ CZ19941725A patent/CZ286600B6/cs not_active IP Right Cessation
- 1994-07-18 MA MA23588A patent/MA23274A1/fr unknown
- 1994-07-19 KR KR1019940017412A patent/KR100373689B1/ko not_active Expired - Fee Related
- 1994-07-19 AU AU67578/94A patent/AU682366B2/en not_active Ceased
- 1994-07-19 UA UA94075643A patent/UA27871C2/uk unknown
- 1994-07-19 CA CA002128378A patent/CA2128378C/en not_active Expired - Fee Related
- 1994-07-19 DZ DZ940084A patent/DZ1801A1/fr active
- 1994-07-20 EP EP94111308A patent/EP0635499B1/en not_active Expired - Lifetime
- 1994-07-20 LV LVP-94-144A patent/LV10950B/en unknown
- 1994-07-20 ES ES94111308T patent/ES2130312T3/es not_active Expired - Lifetime
- 1994-07-20 BG BG98920A patent/BG62196B1/bg unknown
- 1994-07-20 DE DE69416739T patent/DE69416739T2/de not_active Expired - Fee Related
- 1994-07-20 PL PL94304288A patent/PL178152B1/pl not_active IP Right Cessation
- 1994-07-20 TW TW083106624A patent/TW326386B/zh active
- 1994-07-20 BR BR9402868A patent/BR9402868A/pt not_active Application Discontinuation
- 1994-07-20 ZA ZA945345A patent/ZA945345B/xx unknown
- 1994-07-20 US US08/277,800 patent/US5455237A/en not_active Expired - Fee Related
- 1994-07-20 EG EG43694A patent/EG20427A/xx active
- 1994-07-20 AT AT94111308T patent/ATE177087T1/de not_active IP Right Cessation
- 1994-07-20 RO RO94-01230A patent/RO113988B1/ro unknown
- 1994-07-20 DK DK94111308T patent/DK0635499T3/da active
- 1994-07-20 RU RU94026078A patent/RU2142949C1/ru not_active IP Right Cessation
- 1994-07-21 MY MYPI94001897A patent/MY111282A/en unknown
- 1994-07-21 JP JP16955094A patent/JP3662952B2/ja not_active Expired - Fee Related
- 1994-07-21 CN CN94116152A patent/CN1066722C/zh not_active Expired - Fee Related
1995
- 1995-08-30 US US08/521,253 patent/US5587370A/en not_active Expired - Fee Related
1997
- 1997-02-28 BR BR1100149-6A patent/BR1100149A/pt active IP Right Grant
1999
- 1999-04-20 GR GR990401078T patent/GR3029999T3/el unknown

Also Published As

Publication number	Publication date
AU682366B2 (en)	1997-10-02
LV10950B (en)	1996-06-20
SK281778B6 (sk)	2001-07-10
PL178152B1 (pl)	2000-03-31
CZ286600B6 (cs)	2000-05-17
HU212613B (en)	1996-09-30
LV10950A (lv)	1995-12-20
CN1066722C (zh)	2001-06-06
KR950003277A (ko)	1995-02-16
EP0635499B1 (en)	1999-03-03
CA2128378A1 (en)	1995-01-22
RU94026078A (ru)	1996-05-27
HU9302098D0 (en)	1993-11-29
ATE177087T1 (de)	1999-03-15
BR9402868A (pt)	1995-04-04
DZ1801A1 (fr)	2002-02-17
SK85894A3 (en)	1995-03-08
CA2128378C (en)	2005-07-12
MY111282A (en)	1999-10-30
KR100373689B1 (ko)	2003-04-23
EP0635499A2 (en)	1995-01-25
GR3029999T3 (en)	1999-07-30
CZ172594A3 (en)	1995-02-15
DE69416739D1 (de)	1999-04-08
US5455237A (en)	1995-10-03
RO113988B1 (ro)	1998-12-30
DE69416739T2 (de)	1999-07-22
JP3662952B2 (ja)	2005-06-22
EG20427A (en)	1999-04-30
BG98920A (en)	1995-03-31
BR1100149A (pt)	1999-10-05
PL304288A1 (en)	1995-01-23
RU2142949C1 (ru)	1999-12-20
ES2130312T3 (es)	1999-07-01
EP0635499A3 (en)	1995-03-22
ZA945345B (en)	1995-04-25
HUT68547A (en)	1995-06-28
JPH07309848A (ja)	1995-11-28
UA27871C2 (uk)	2000-10-16
TW326386B (en)	1998-02-11
AU6757894A (en)	1995-02-02
CN1105025A (zh)	1995-07-12
MA23274A1 (fr)	1995-04-01
US5587370A (en)	1996-12-24
DK0635499T3 (da)	1999-09-27

Publication	Publication Date	Title
BG62196B1 (bg)	1999-05-31	Нови тетразинови производни с акарицидна активност
JP2552811B2 (ja)	1996-11-13	殺虫作用のあるフェニルヒドラジン誘導体
RU2109730C1 (ru)	1998-04-27	Фенилгидразиновые производные, способ борьбы с вредителями и инсектоакарицидонематоцидная композиция
KR100229087B1 (ko)	1999-11-01	제초제로서의 카복스아미드 유도체,그들의 제법 및 이를 함유하는 제초 조성물
JP2022536757A (ja)	2022-08-18	縮合複素環式化合物及び害虫駆除剤としてのその使用
SU1501911A3 (ru)	1989-08-15	Инсектицидна композици (ее варианты)
KR900008839B1 (ko)	1990-11-30	1,3-디티안류의 제조방법
CA1181403A (en)	1985-01-22	1-phenoxy(phenylthio)-4-arylalkynyloxy-benzene derivatives endowed with a juvenil hormonic and an acaricide activity
EP0003430B1 (en)	1982-01-06	Novel 2,6-dinitrobenzenamines, their preparation, composition containing them and their use as fungicides
EP0101288A2 (en)	1984-02-22	Aryl(aryloxy or arylthio)azolomethanes, their preparation and their use
JP4796594B2 (ja)	2011-10-19	殺虫、殺ダニ、及び殺菌ニトロメチレン化合物
CN112624993A (zh)	2021-04-09	含氮杂环结构的噁唑啉类衍生物及其制备和在防治植食性螨中的应用
JP2502561B2 (ja)	1996-05-29	ピリジニウム内部塩及びイリド
KR830002348B1 (ko)	1983-10-24	1-벤조일-3-피리디닐 우레아화합물의 제조방법
EP1364951B1 (en)	2012-05-02	Triazoquinolone derivatives as pest controllers
WO2026041112A1 (zh)	2026-02-26	一种含硫取代的间二酰胺类化合物、其制备方法、组合物和应用
MXPA94005572A (en)	2000-08-01	Active derivatives of tetrazine acaricidically novedo
JPS5823872B2 (ja)	1983-05-18	Ｎ↓−ベンゾイル↓−ｎ′↓−ピリジルオキシフエニルウレア系化合物、それらの製造方法及びそれらを含有する殺虫剤
JPH02279662A (ja)	1990-11-15	オキシムエーテルおよびこれを含有する有害生物防除剤
WO2026081989A1 (zh)	2026-04-23	一种含芳环或芳杂环取代的间二酰胺类化合物、其制备方法、组合物和应用
JPH03176479A (ja)	1991-07-31	キノキザリン類及び害虫防除剤
CS208686B2 (en)	1981-09-15	Insecticide and acaride means
JPH02152943A (ja)	1990-06-12	ナフトキノン系化合物、それを含む殺ダニ剤およびダニ類を防除する方法
JPS6225143B2 (pt)	1987-06-01
IE47002B1 (en)	1983-11-30	Novel 1-(mono-o-substituted benzoyl)-3-(substituted pyrazinyl) ureas and their preparation