前苏联专利SU1748628A3 Acaricidal composition

专利PDF首页>>前苏联专利

专利附录

专利说明

权利要求

类似技术

同族专利

引用文献

法律状态

优先权

专利摘要:
Novel pyridazinone derivatives of the general formula (I): …<CHEM>… wherein R represents a straight or branched chain alkyl group having 2 to 6 carbon atoms, A represents halogen atom, alkoxy group having 1 to 4 carbon atoms or alkylthio group having 1 to 4 carbon atoms, X represents oxygen atom or sulfur atom,… B represents …<CHEM>… Y represents oxygen atom, sulfur atom, …<CHEM>… V represents oxygen atom or sulfur atom,… R<1> and R<2> represent independently hydrogen atom or alkyl having 1 to 4 carbon atoms,… R<3> and R<6> represent independently hydrogen atom, halogen atom, alkyl having 1 to 4 carbon atoms, cyano group, haloalkyl group having 1 to 4 carbon atom or alkoxycarbonyl group having 1 to 4 carbon atoms, R<7> represents alkyl group having 1 to 4 carbon atoms or alkylcarbonyl group having 1 to 4 carbon atoms and Z represents various specific organic groups. A process for preparation of said derivatives is also provided. These derivatives are useful as an active ingredient of insecticidal, acaricidal, nematicidal and/or fungicidal compositions for agricultural and horticultural uses as well as of expellent compositions for ticks parasitic on animals.
公开号:SU1748628A3
申请号:SU874028993
申请日:1987-02-06
公开日:1992-07-15
发明作者:Накадзима Ясуюки；Кавамура Ясуо；Огура Томоюки；Макабе Такахиро；Хирата Киминори；Кудо Масаки；Отиаи Есинори；Хиросе Масаеси
申请人:Ниссан Кемикал Индастриз Лтд (Фирма)；
IPC主号:

专利说明:

The invention relates to chemical plant protection products, namely, an acaricidal composition based on pyridazinone derivatives. Acaricidal compositions based on 2-tert-butyl-4-chloro-3 (2H) pyridazin-3-one are known.
However, they have insufficient activity.
The aim of the invention is to enhance the acaricidal activity.
This goal is achieved by using a composition- containing the active ingredient, a derivative of 3 (2H) -pyridazinone of the general formula l
I c.
tertgStsN9-}
R H2
Ñсн2сиг-о-С
3
where R is methyl or chlorine;
R- is methyl or chlorine;
C-C-alkyl, ethoxy, chlorine,
benoxy, benzoyl,
surfactant — Sorpol 2680 based on polyoxyethylene alkylaryl ether and sodium alkyl benzenesulfonate or a mixture of Sorpol 5039 based on polyoxyethylene alkyl aryl ether, sulfate and white carbon black and calcium ligninsulfonate in a 4: 2 mass ratio or a mixture of Sorpol 3353 on a basis polyoxyethylene styrylphenyl ether and polyoxyethylene polyoxypropylene block copolymer and Runox-1000 C based on naphthylmethanesulfonate sodium at a mass ratio of 10: 0.5, carrier - Zeklit PFR based on kaolinite and sericite or cc ilo00
and you
00
la and K, N-dimethylformamide at a mass ratio of 55: 20 with the following content of ingredients, wt.h:
Active ingredient 20 - 25 Surfactant 5 - 10 MediaOther
The composition may additionally contain a 1% aqueous solution of Santan gum in an amount of 20 May.
The compounds used as active1 of the ingredient of the composition can be prepared by reacting a compound of the general formula:
1 About Tpei-c Hg-N vtt (P)
with a compound of the general formula:
Rl
and
x -sn2sn2-o
am
thirty
de X and X is a halogen atom, -SM, de M is a hydrogen atom or a jaw metal atom.
In the general case, it is preferable to use - SM as X in the general formula (ill), when X in the general Formula (II) is a halogen atom, and to use a talone-35 atom as X in the general formula (ill), when X in total l (II) is SM (where M is a hydrogen or alkali metal atom), provided that when X is a halogen atom, X is SH, and when X is SM, then X is a halogen atom.
It is also preferred to prepare the compounds of the invention in the presence of suitable bases and in solvents that do not adversely affect the course of the reaction. When M is an alkali metal atom, the presence of a base is optional.
As solvents, lower alcohols such as methanol, ethanol and the like can be used; ketones, such as acetone, methyl ethyl ketone and the like; hydrocarbons, such as benzene, toluene and the like; ethers such as propyl ether, tetrahydroirene, 1, 4-dioxane and the like;
,
five
0
five
0
35

amides, such as And, K-dimethylprmide, -hexamethylphosphoric triamides, etc., halogenated hydrocarbons, such as dichloromethane, dichloroethane, etc. If necessary, mixtures of these solvents or mixtures of these solvents and water can also be used.
Inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, acid sodium carbonate, and the like, and organic bases such as sodium methyl acetate, sodium ethoxide, tristilamine, pyridine, and the like. If necessary, tetraammonium salts, for example, triethylbenzylammonium chloride and the like can be added to the reaction system as a catalyst.
The reaction temperature may range from -20 ° C to the boiling point of the solvent used in the reaction. The reaction temperature is preferably from -5 ° C to the boiling point of the solvent used in the reaction.
A certain choice of the ratio of raw materials is optional, but it is preferable to conduct the reaction using an equimolar or no 4 jn equimolar amount of materials.
Example. Getting connected and k,
tert-with Nd-Y-Ch-01 SЈ
S-CH2CH2-0- -C5H7
CH3
To a mixture of 2, 2-tert-butyl-4-chloro-5-mercapto-3 (2H) -pyridazinone,% 2.9 g of 2- (2-chloro-6-methyl-V-propylphenoxy) -ethyl bromide and 50 ml of DMF (dimethylformamide), cooled in an ice bath, add k, 2 g of anhydrous potassium carbonate and stir for 5 h. The reaction mixture is mixed with ice water, extracted with chloroform, washed with water and dried. Then, chloroform is distilled off to obtain the crude product of the intended substance. The crude product thus obtained is purified by column chromatography with
obtaining 3.0 g of substance № in the form of oil.
NMR (CDCI-., Y): 0.92 (t., ZN); 1.5-1.9 (m, 2H); 1.62 (s., 9H), 2, 2 (s., 3N); 2.5 (t, 2H); 3.2 (t; 2H); k, I (t, 2H); 6.8 - 7.0 (m, 2H), 7.72 (s., 1H).
PRI mme R 2. Getting connection 6
v5L "CU
tert -StsN9- 5 sn SNg 0 sh (SNe C1
I
To a mixture of 1 g of 2-tert-butyl-1-chloro-5-mercapto-3 (2H) -pyridazinone, 1, g of 2- (2 g, 6-dichloro-isopropylphenoxy) ethyl bromide and 20 ml of DMF cooled in an ice bath, 1.9 g of anhydrous potassium carbonate is added and stirred for 5 hours. The reaction mixture is mixed with ice water, extracted with chloroform, washed with water and dried. Then, chloroform is distilled off to obtain a crude product / intended substance. The crude product thus obtained is purified by column chromatography to obtain 1, t g of substance 6 as an oil. l
NMR (AHSC, ff): 1.20 (d, 6H); f, 62 (s. 9H); 2.80 (q.c., 1H); 3.8 (TV, 2H); A, 22 (t, 2H); 7.08 (s, 2H); 7.68 (s, 1H).
Example 3. Preparation of Compound 7
About Tper-C Hg-N-Jyci
C1 N S-CHjCfy-O-, -0-С4Н9-ter
- To a mixture of 1 g of 2-tert-butyl-chloro-5-mercapto-3- (2H) -pyridazinone, 1.5 g of 2- (2, 6-dichloro-4-tert-butylphenoxy} ethyl bromide and 20 ml of DMF cooled in an ice bath add 1.9 g of anhydrous potassium carbonate and mix for 5 hours.
In 50 ml of M, M-dimethylformamide, 6.6 g of 2-tert-butyl-chloro-5-mercapto-3 (2H) -pyridazinone and 10 2- (2f, 6-dimethyl-4-benzoylphenoxy) ethyl bromide and to 5 g of anhydrous sodium carbonate is added thereto. The solution is stirred at room temperature for 17 hours. The resulting solution is poured into water and extracted with diethyl ether. The organic layer is dried over anhydrous.
The reaction mixture was mixed with ice-cold sodium sulfate and the solvent was removed by extraction, extracted with chloroform, washed with water and dried. Then chloroform is distilled off to obtain the crude product of the proposed substance.
chase under reduced pressure. The crude product thus obtained is purified by column chromatography (on silica gel, eluting
The crude product thus obtained was purified by column chromatography to obtain 1.3 g of substance 7 as an oil.
NMR (CDC1 c. #): 1.26 (s, 9H); 1.65 (s, 9H); 3.6 (t, 2H); , 25 (t, 2H); 7.27 (s, 2H); 7.70 (s.,
1H).
N p 1
and me b b. Getting connection tert-C Nd-KC
N S-CH2CH2-015
five
0
five
To a mixture of 65 g of 2-tert-butyl-4-chloro-5-mercapto-3- (2H) -pyridaine, 96 g of 2- (2,6-dimethyl-phenoxy-5 phenoxy) ethyl bromide and 350 ml DMF, cooled in an ice bath, was added 123 g of anhydrous potassium carbonate with stirring for 5 hours. The reaction mixture was mixed with ice water, extracted with chloroform, washed with water and dried. Then chlorolorm is distilled off to obtain the crude product of the proposed substance. The crude product / thus obtained is recrystallized from acetonitrile to obtain 92 g of substance and 1 as pale yellow crystals „
M.p. 119.3-120.4 s.
Example 5 Preparation of 2-tert-butyl-chloro-5- (2) -2, b -Dimethyl-4-benzoyl-phenoxy (ethylthio) -3- (2H1-pyridazinone (compound 15 ).
In 50 ml of M, M-dimethylformamide, 6.6 g of 2-tert-butyl-chloro-5-mercapto-H (2H) -pyridazinone and 10 g of 2- (2f, 6-dimethyl-4-benzoylphenoxy) - ethyl bromide and to it 5 g of anhydrous sodium carbonate is added. The solution is stirred at room temperature for 17 hours. The resulting solution is poured into water and extracted with diethyl ether. The organic layer is dried over anhydrous.
sodium sulfate and the solvent is distilled off under reduced pressure. The crude product thus obtained is purified by column chromatography (on silica gel, eluting
benzene) and crystallization (from 50 m of n-hexane) diethyl ether (k: 1 to obtain 13.3 g of the target compound, mp. 9.6 - 96.2 C.
Similarly, the compounds shown in Table 1 were prepared. EXAMPLE 6 Emulsifiable concentrates. The composition contains, as: Active ingredient 20 Xylene 55
M, M-dimethylformamide 20 Sorpol-2680 (mixture of polyoxyethylene alkyl-aryl ether and sodium alkyl benzene sulfonate) 5
These components are thoroughly mixed with the formation of emulsifiable concentrate. When consumed, the emulsifiable concentrate is diluted with water.
Example. Wettable powders, hours:
The active ingredient 25 Zeklit-PPK (a mixture of kaolinite and sericite) 66 Sorpol-5039 (a mixture of polyoxyethylene alkyl aryl ether, sulfate and white soot) Кар Karplex-80 (trade mark, white carbon black) 3 Calcium lignone sulfonate 2 These components are thoroughly mixed to form homogeneous mixture and grind to form a wettable powder. When consumed, the wettable powder is diluted with water to a concentration.

and m h .:
eight
e p. 8. Spreading
five
0
five
0
five
Yes
The active ingredient is 25 Sorpol-3353 (a mixture of polyoxyethylenethyrylphenyl ether and polyoxyethylenepolyoxypropylene block copolymer Runox-UOOC (naphthylmethanesulfonate sodium) 0.5 1% aqueous solution of xanthan gum (natural high molecular weight - i liter connection) 20 Water ЦЦ9 $
| TO
PRI me R 9. Acaricidal test against spider mite Kanzawa (oT.Kanzawai).
The leaf of an ordinary bean is cut with a shock leaf bur in a round area 1.5 cm in diameter and then smeared on a moistened filter paper on a 7 cm diameter polystyrene dish. Each piece of leaf is inoculated with ten spider kanchik nymphs. After 0.5 days after inoculation, every 2 ml of an aqueous emulsion containing 500 ppm, of the proposed compound, obtained by diluting a 20% emulsifiable concentrate with water containing a filler, is added to each polystyrene cup using a rotary irrigation tower. After 96 hours, mortality rates are determined according to the following equation:
Mortality (%) - stork. schikov
the number of remaining mites
The test is repeated twice for each compound.
As a result, 100% mortality is observed when using compounds 1 - 15.
PRI me R 10. Acaricidal test against the spider mite Kanzawa (T “Kanzawai).
The leaf of common bean is cut with an impact drill for leaves into round pieces with a diameter of 1.5 cm and then placed on moistened filter paper on a polystyrene dish with a diameter of 7 cm. Each piece is
five
The leaf check is inoculated by ten nymphs with spider mites Kanzawa. After 0.5 days after inoculation, every 2 ml of an aqueous emulsion containing 500 ppm of the proposed compound, obtained by diluting a 25% wettable powder with water containing a filler, is applied to each polystyrene cup using a rotary irrigation tower. After 96 hours, the mortality of the nymphs was determined according to the equation described in Example 9. The test was repeated two times.
for each compound, using compounds 1-15, 100% is observed for mortality.
PRI me R 11. Acaricidal test against spider kleshik.
The leaf of an ordinary bean is cut with a shock leaf bur into 1.5 cm diameter round pieces, then placed onto a moistened filter paper on a polystyrene cup with a diameter of 7 cm. Each piece of a leaf is inoculated with ten nymphs with a spider Kanzawa mites. After 0.5 days after inoculation, every 2 ml of an aqueous emulsion containing 500 ppm of the proposed compound obtained by diluting a 25% flowable composition with water containing a filler is applied to each polystyrene cup using a rotating irrigation tower. After 96 h, nymph mortality is determined.
according to the equation described in Example 9. The test was performed twice for each compound.
As a result of this compound 1-15, 100% mortality
Example 12 (comparative). Acaricidal test against - spider mite Kanzawa (T, Kanzawa i)
The test is carried out in accordance with Example 9, however, the concentration of each of the proposed and control compounds is changed to 500 and 100 ppm.
The results of the experiments are given in table 2.
As can be seen from the data of Tables 1 and 2, the compounds of the invention exhibit a higher -acaricidal activity than the known control compounds.
tert WITH
F
0
formula of invention
1. An acaricidal composition comprising the active ingredient, a production of aqueous 3 (2H) -pyridazinone, a surfactant and a carrier, characterized in that, in order to enhance acaricidal activity, as a derivative of 3 (2H) -pyridazinone it contains compound of general formula O
.twl;

权利要求:
Claims (2)
[1]
1 SCH2CH2-0-C
ain
s
m
Where
to
R2
R3
20
25
thirty
methyl or chlorine;
methyl or chlorine;
C-C-alkyl, ethoxy, chlorine,
phenoxy, benzoyl, as a surfactant — Sorpol-2680 based on polyoxyethylene alkylaryl ether and sodium alkyl benzenesulfonate or a mixture of Sorpol 5039 based on polyoxyethylene alkylaryl ether, sulfate and white soot and calcium ligninsulfonate in a 4: 2 ratio, 2 or 2, or a section in a mixture of 4: 2, or a section or a section; polyoxyethylene styrylphenyl ether and polyoxyethylene polyoxypropane maple block copolymer and Runox-UOOC based on naphthylmethanesulfonate sodium in a mass ratio of 10: 0.5, and Zeklit PFR n as a carrier based on kaolinite and sericite or a mixture of xylene and N, N-dimethylformamide at a weight ratio of 55: 20, with the following contents of ingredients, wt 'h .: said active ingredient is 20 - 25; said surfactant 5-10; the specified carrier is the rest.
[2]
2. The composition according to claim 1,. O of tl and - so that it additionally contains C-nth vnsdny solution of xanthan gum in an amount of 20 wt. About .Table
-rV
N X-B-Y35
40
45
M9
Zn
Continuation of table 1

类似技术:

公开号 | 公开日 | 专利标题

SU1748628A3|1992-07-15|Acaricidal composition

KR960012178B1|1996-09-16|Pyrimidine derivatives, process for their production, and herbicidal method and composition

KR930009443B1|1993-10-04|Phenoxyalkylamine derivative production

RU2054422C1|1996-02-20|Derivatives of 3|-pyridazinone

EP0199281B1|1991-07-10|Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions

EP0238711B1|1990-11-28|Thiadiazabicyclononane derivatives, processes for their production and herbizidal compositions

EP0183212B1|1990-06-20|Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions

EP0088384B1|1986-12-30|Pyridazinone derivatives, preparation thereof, and agricultural and horticultural fungicidal, insecticidal, acaricidal, nematicidal compositions containing said derivatives

EP0394889A2|1990-10-31|Heterocyclic diones as pesticides and plant growth regulators

US4264606A|1981-04-28|Insecticidal and acaricidal phenylcyclo-propane carboxylic acid derivatives and insecticidal and acaricidal compositions thereof

EP0481512A1|1992-04-22|3-Alkoxyalkanoic acid derivative, process for preparing the same and herbicide using the same

KR960012172B1|1996-09-16|Pyrazole derivative and insecticidal and miticidal composition containing the derivative as active ingredient

US4012519A|1977-03-15|Fungicidal 3-| lactones and lactams

GB2205316A|1988-12-07|Herbicidal benzoyl pyran, thiopyran or piperidine compounds

US4938790A|1990-07-03|Herbicidal 12-substituted 12H-dibenzo|dioxocin-6-carboxylic acids

EP0427445B1|1994-06-08|Benzylideneaminoxyalkanoic acid | amide derivative, process for preparing the same and herbicide

US4215122A|1980-07-29|4-Alkyl- and 4-allyl-mercapto-, -sulfinyl- and -sulfonyl-methyl-2-amino-6-N,N-dimethylcarbamoyloxy-pyrimidines, processes for producing them, compositions containing these pyrimidines, and the use thereof for controlling insect pests

WO1995025730A1|1995-09-28|Nicotinic acid derivative and herbicide

US4456467A|1984-06-26|1-Methylene carbonyl derivatives of 3-aryloxy-4-phenyl-azet-2-one

CA1237721A|1988-06-07|Pyridazinone derivatives, preparation thereof, andagricultural and horticultural fungicidal,insecticidal, acaricidal, nematicidal compositionscontaining said derivatives

GB2041353A|1980-09-10|Process for preparing triazolidine derivatives

US5235092A|1993-08-10|Phenoxyacetic acid derivatives and plant growth regulating agents containing them as active ingredients

US4999448A|1991-03-12|Method of preparing bis-phenol ethers

KR960012175B1|1996-09-16|Pyridazinone compounds derivative and composition for controlling and/or preventing insect pests

US4210592A|1980-07-01|Thiophosphoro-S-acylated hydrazones

同族专利:

公开号 | 公开日

BR8700556A|1987-12-08|

ES2036531T3|1993-06-01|

KR900006852B1|1990-09-22|

AU594115B2|1990-03-01|

HU200653B|1990-08-28|

CS273321B2|1991-03-12|

AR244212A1|1993-10-29|

TR23155A|1989-04-18|

NZ219188A|1989-03-29|

AU6823987A|1987-08-13|

DE3778924D1|1992-06-17|

YU45934B|1992-09-07|

US4906627A|1990-03-06|

EG18275A|1993-02-28|

CN87100878A|1987-09-23|

CA1286298C|1991-07-16|

EP0232825B1|1992-05-13|

IL81479D0|1987-09-16|

IN165467B|1989-10-28|

PL150723B1|1990-06-30|

DD265402A5|1989-03-01|

PL263992A1|1988-08-18|

HUT44410A|1988-03-28|

IE870315L|1987-08-08|

KR870007899A|1987-09-22|

ZA87704B|1987-09-30|

CS71587A2|1990-07-12|

EP0232825A3|1987-10-28|

YU16487A|1988-08-31|

EP0232825A2|1987-08-19|

CN1017427B|1992-07-15|

引用文献:

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

RU2455004C1|2011-04-01|2012-07-10|Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Ярославский государственный технический университет" |Method for producing sulphochlorides of 6-arylpyridazine-3-ones|US2832780A|1955-09-14|1958-04-29|Warner Lambert Pharmaceutical|Hydrazides of pyridazonyl-substituted alkanoic acids|

NL269094A|1960-09-09|

US3346577A|1963-07-01|1967-10-10|Sumitomo Chemical Co|Method for the preparation of 4-amino-3 pyridazinones|

US4177273A|1977-02-14|1979-12-04|Sandoz, Inc.|6--4,5-dihydro-pyridazin-3-ones|

DE3143303A1|1981-10-31|1983-05-11|Basf Ag, 6700 Ludwigshafen|PYRIDAZINONE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES|

US4571397A|1982-03-05|1986-02-18|Nissan Chemical Industries|Pyridazinone derivatives, preparation thereof, and agricultural and horticultural fungicidal, insecticidal, acaricidal, nematicidal compositions containing said derivatives|

DE3321007A1|1983-06-10|1984-12-13|Basf Ag, 6700 Ludwigshafen|SUBSTITUTED 4,5-DIMETHOXYPYRIDAZONE, METHOD FOR THE PRODUCTION THEREOF, HERBICIDES CONTAINING THEM AND THEIR USE FOR CONTROLLING UNWANTED PLANT GROWTH AS HERBICIDES|

GR79933B|1983-06-23|1984-10-31|Nissan Chemical Ind Ltd|

DE3328770A1|1983-08-10|1985-02-28|Basf Ag, 6700 Ludwigshafen|PYRIDAZINONE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES|

EP0183212B1|1984-11-29|1990-06-20|Nissan Chemical Industries Ltd.|Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions|

CA1265798A|1984-12-10|1990-02-13|Motoo Mutsukado|3pyridazinone, process for its preparation andanti-allergic agent containing it|

US4837217A|1985-04-19|1989-06-06|Nissan Chemical Industries, Ltd.|Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions|

US4945091A|1987-07-30|1990-07-31|Nissan Chemical Industries, Ltd.|3-pyridazinone compounds derivatives and compositions for controlling and/or preventing insect pests intermediates for such compounds, and a process for their manufacture|

JP4211905B2|1999-09-29|2009-01-21|株式会社大都製作所|vending machine|

CA2394826C|2000-01-07|2010-03-23|Aware, Inc.|Systems and methods for loop length and bridged tap length determination of a transmission line|

WO2001080580A1|2000-04-04|2001-10-25|Seung Han Song|Information management system by means of portable appliances via wire or wireless internet and the method for the same|

CN1440256A|2000-05-08|2003-09-03|布雷恩斯盖特有限公司|Method and apparatus for stimulating sphenopalatine ganglion to modify properties of BBB and cerebral blood flow|

DE10115698A1|2001-03-29|2002-10-10|Degussa|Metal-free silane-terminated polyurethanes, a process for their production and their use|

JP4311906B2|2002-02-26|2009-08-12|コクヨ株式会社|table|

JP4311907B2|2002-02-28|2009-08-12|株式会社リコー|Organic thin film, method for producing the same, and optical recording medium using the same|

JP4311908B2|2002-03-15|2009-08-12|株式会社堀鐵工所|Drilling device|

EP1626473A1|2003-11-20|2006-02-15|Matsushita Electric Industrial Co., Ltd.|Power supply for vehicle|EP0183212B1|1984-11-29|1990-06-20|Nissan Chemical Industries Ltd.|Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions|

US4837217A|1985-04-19|1989-06-06|Nissan Chemical Industries, Ltd.|Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions|

EP0283271A3|1987-03-17|1990-04-25|Ube Industries, Ltd.|Pyridazinone derivative, process for producing thereof and insecticide, acaricide and fungicide containing said derivative as active ingredient|

EP0331529A3|1988-03-03|1991-11-21|Ube Industries, Ltd.|Diphenyl ether derivatives, process for producing the same and insecticide and acaricide containing the same as active ingredient|

DE3824211A1|1988-07-16|1990-01-18|Basf Ag|2-TERT.-BUTYL-4-CHLORINE-5--3-PYRIDAZINONE FOR CONTROLLING SNAILS|

US5004744A|1988-12-13|1991-04-02|Bayer Aktiengesellschaft|Pyridazinones as pesticides|

IT1229684B|1989-04-05|1991-09-06|Mini Ricerca Scient Tecnolog|PYRIDAZINONE WITH INSECTICIDE AND ACARICIDE ACTIVITY|

US5278163A|1989-05-17|1994-01-11|Nissan Chemical Industries, Ltd.|Pyridazinone derivatives and compositions for controlling and/or preventing insect pests|

IL94394A|1989-05-17|1994-10-21|Nissan Chemical Ind Ltd|Pyridazinone derivatives, process for their preparation and compositions for controlling and/or preventing insects, acarides, nematodes and molluscs|

EP0665223A1|1994-01-28|1995-08-02|Takeda Chemical Industries, Ltd.|Antitumor agent, novel 3-pyridazinone derivatives and their preparation|

CZ294096B6|1995-01-20|2004-10-13|Americanácyanamidácompany|Benzophenone compounds, process of their preparation, fungicidal agents containing thereof and plant protection method|

CN101637163B|2009-09-07|2012-07-04|山东农业大学|Pesticide combination containing pyridaben and pymetrozine|

CN105924432B|2016-07-13|2018-08-24|青岛农业大学|Pyridazinone derivative and its preparation method and application|

法律状态:

优先权:

申请号 | 申请日 | 专利标题

JP2497886|1986-02-08|

[返回顶部]