SU645518A3 - Method of fighting weeds - Google Patents

Method of fighting weeds

Info

Publication number
SU645518A3
SU645518A3 SU772464007A SU2464007A SU645518A3 SU 645518 A3 SU645518 A3 SU 645518A3 SU 772464007 A SU772464007 A SU 772464007A SU 2464007 A SU2464007 A SU 2464007A SU 645518 A3 SU645518 A3 SU 645518A3
Authority
SU
USSR - Soviet Union
Prior art keywords
phenoxy
acid
trifluoromethylphenoxy
dichlorophenoxy
chlorophenoxy
Prior art date
Application number
SU772464007A
Other languages
Russian (ru)
Inventor
Хандте Райнхард
Кох Манфред
Херляйн Герхард
Кехер Хельмут
Лангелюддеке Петер
Original Assignee
Хехст Аг (Фирма)
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 Хехст Аг (Фирма) filed Critical Хехст Аг (Фирма)
Application granted granted Critical
Publication of SU645518A3 publication Critical patent/SU645518A3/en

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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
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • C07C41/50—Preparation of compounds having groups by reactions producing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/194—Radicals derived from thio- or thiono carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
    • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic System without C-Metal linkages

Description

Соединени  формулы I получают различными известными способами. Одним из них  вл етс  сиособ, основанный на взаимодействии соответствующих гидроксизамещенных дифениловых эфиров с 2-галоидпропионовой кислотой или ее производПо предлагаемому способу примен ют следующие соединени  общей формулы I. 1. (4 -Хлорфенокси) -фенокси -пропионитрил . 2.(4 - Трифторметилфено си) - фенокси -пропионитрил . 3. (2 -Хлор-4 -трифторметилфенокси ) -фенокси -пропионитрил. 4.2-|4-(2, 4 -Дихлорфенокси) -фенокси пропионитрил . 5.(2 -Хлор-4 -бромфенокси) -фепокси -пропионитрил . 6.Амид (4 -Хлорфенокси)-фенокси тиопропионовой кислоты. 7.Амид 2- 4-{4 -Трифторметилфенокси) фенокси -тиопропионовой кислоты. 8.Амид (2, 4 -Дихлорфенокси) -фе нокси -тиопропио,новой кислоты. 9.Амид (2 -Хлор-4 -бромфенокси)фенокси -тиопропионовой кислоты. 10.Амид (2 -Хлор-4 -трифторметилфенокси ) -фенокси -тиопропионовой кислоты. 11.Бутиламид (4 -Трифторметилфенокси ) -фено1К1Си -пиопропионовой кислоты. 12.Бензиламид (,ифторметилфенокси ) -фенокси -тиопропионовой кислоты. 13.Бутиламид (4 -хлорфенокси)-фенокси -тиопропионовой кислоты. 14. (4 -Трифторметилфенокси)-фенокси - - (тетразол-5-ил) -этан. 15.1-{4-(2,4 -ДИхлорфенокси)-фенокси 1- (тетразол-5-ил) -этан. 16.(4 -Хлорфенокси)-фенокси - 1{тетразол-5-ил ) -этан. 17.Продукт присоединени  бисульфита натри  к (2,4 -1Дихлорфенокси)-фенокси -пропионовому альдегиду формулы О-СН-СН- SOjNa CHj ОН 18.Продукт присоединени  бисульфита натри  к (4 -трифторметилфенокси)фенокси -пропионовому альдегиду. 19.Продукт присоединени  бисульфита натри  к (4 -хлорфенокси)-фенокси пропионовому альделиду. 20. (2,4 -Дихлорфенокси) -фенокси -пропан-диэтилацеталь . 21.(4 -Хлорфенокси) -фенокси -пропан-диэтилацеталь . 22.,4 -Дихлорфенокси) -фенокси пропан-метил-этилацеталь . 23. (4 -Трифторметилфенокси -фенокси -пропан-диметилацеталь . 24. (2,4 -Дихлорфенокси) -фенокси -пропан-пропилимин . Пример 1. Семена опытных растений высевают в специальные горщочки, и на поверхность почвы нанос т действующие вещества в форме порощка. После этого горщочки выдерживают 4 недели в услови х теплицы, а затем оценивают гербицидньтй эффект. Шкала оценки представлена в табл. 1. Дл  сравнени  используют известные гербициды А-2-нит.ро-4-т,ргИфторметил-4нитро-дйфениловый эфир ;и Б-2-(2-метил4-хлорфенокси )-пропионовую кислоту. Результаты опыта представлены табл. 2. The compounds of formula I are prepared by various known methods. One of them is a synthetic method based on the interaction of the corresponding hydroxy-substituted diphenyl ethers with 2-halopropionic acid or its production. The following compounds of general formula I are used in the proposed method. (4-Chlorophenoxy) phenoxy-propionitrile. 2. (4 - Trifluoromethylpheno sy) - phenoxy-propionitrile. 3. (2-Chloro-4-trifluoromethylphenoxy) -phenoxy-propionitrile. 4.2- | 4- (2, 4-Dichlorophenoxy) -phenoxy propionitrile. 5. (2-Chloro-4-bromophenoxy) -fepoxy-propionitrile. 6. Amide (4-Chlorophenoxy) -phenoxy thiopropionic acid. 7. Amide of 2-4- {4-Trifluoromethylphenoxy) phenoxy-thiopropionic acid. 8. Amide (2, 4-Dichlorophenoxy) -phenoxy-tiopropio, nova acid. 9. Amide (2-Chloro-4-bromophenoxy) phenoxy-tiopropionic acid. 10. Amide (2-Chloro-4-trifluoromethylphenoxy) -phenoxy-thiopropionic acid. 11. Butylamide (4-trifluoromethylphenoxy) -pheno1K1Ci-pyopropionic acid. 12. Benzylamide (, ifluoromethylphenoxy) -phenoxy-thiopropionic acid. 13. Butylamide (4-chlorophenoxy) -phenoxy-thiopropionic acid. 14. (4-Trifluoromethylphenoxy) -phenoxy - - (tetrazol-5-yl) -ethane. 15.1- {4- (2,4 -Dichlorophenoxy) -phenoxy 1- (tetrazol-5-yl) -ethane. 16. (4-Chlorophenoxy) -phenoxy-1 {tetrazol-5-yl) -ethane. 17. The product of the addition of sodium bisulfite to (2.4 -1 Dichlorophenoxy) -phenoxy-propionic aldehyde of the formula O-CH-CH-SOjNa CHj OH 18. The product of the addition of sodium bisulfite to (4-trifluoromethylphenoxy) phenoxy-propionic aldehyde. 19. Addition product of sodium bisulfite to (4-chlorophenoxy) -phenoxy propionic aldelic. 20. (2,4-Dichlorophenoxy) -phenoxy-propane-diethylacetal. 21. (4-Chlorophenoxy) -phenoxy-propane-diethylacetal. 22., 4-Dichlorophenoxy) -phenoxy-propane-methyl-ethyl ethyl. 23. (4-Trifluoromethylphenoxy-phenoxy-propane-dimethyl acetal. 24. (2,4-Dichlorophenoxy) -phenoxy-propane-propylimine. Example 1. The seeds of the experimental plants are sown in special plants and the active substances are applied to the soil surface After this, the pods are kept for 4 weeks under greenhouse conditions, and then the herbicidal effect is evaluated. The rating scale is shown in Table 1. For comparison, the known herbicides A-2-nit.ro-4-t, regiFluoromethyl-4-nitrodiphenyl ether are used. ; and B-2- (2-methyl 4-chlorophenoxy) -propionic acid. The results of the experiment p edstavleny Table. 2.

1 а б л и ц а 21 a b l and c a 2

Довсходовое применениеPre-emergence application

Примечание: Прочерк означает, что опыт не проводили.Note: A dash means that the experiment was not performed.

Пример 2. Опытные растени , выращенные в услови х теплицы, обрабатывают действующими веществами в форме порошка. Через 4 недели после обработкиExample 2. Experimental plants grown under greenhouse conditions are treated with active substances in powder form. 4 weeks after treatment

Послевсходовое применениеPost-harvest application

Пример 3. Семена опытных культур- 5 ных растений высаживают в почву, которую затем обрабатывают действующими веществами в дозе 2,5 кг/га.Example 3. Seeds of experimental cultivated plants are planted in soil, which is then treated with active ingredients at a dose of 2.5 kg / ha.

8eight

оценивают гербицидный эффект по примеру 1.evaluate the herbicidal effect of example 1.

Результаты опыта представлены в табл. 3.The results of the experiment are presented in table. 3

Таблица 3Table 3

Результаты опыта представлены вThe results of the experiment are presented in

табл. 4.tab. four.

Таблица 4Table 4

10ten

отличающийс  тем, что, с целью повышени  эффективности способа, в качестве производных дифенилового эфира используют соединени  общей формулыcharacterized in that, in order to increase the efficiency of the process, compounds of the general formula are used as derivatives of diphenyl ether

Claims (2)

1.За вка ФРГ № 2433067, кл. С 07 С 30 69/67, опублик. 29.01.1976.1. Forward Germany No. 2433067, cl. C 07 C 30 69/67, published 01/29/1976. 2.Патент Швейцарии № 508338, кл. А 01 N 9/02, опублик. 1971.2. The patent of Switzerland No. 508338, cl. And 01 N 9/02, published. 1971.
SU772464007A 1976-03-31 1977-03-29 Method of fighting weeds SU645518A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19762613697 DE2613697A1 (en) 1976-03-31 1976-03-31 HERBICIDAL AGENTS

Publications (1)

Publication Number Publication Date
SU645518A3 true SU645518A3 (en) 1979-01-30

Family

ID=5973954

Family Applications (1)

Application Number Title Priority Date Filing Date
SU772464007A SU645518A3 (en) 1976-03-31 1977-03-29 Method of fighting weeds

Country Status (23)

Country Link
JP (1) JPS52120125A (en)
AR (1) AR226410A1 (en)
AT (1) AT354801B (en)
AU (1) AU505610B2 (en)
BE (1) BE853104A (en)
BG (1) BG27722A3 (en)
BR (1) BR7702022A (en)
CA (1) CA1095735A (en)
CH (1) CH629073A5 (en)
DD (1) DD130620A5 (en)
DE (1) DE2613697A1 (en)
FR (1) FR2346329A1 (en)
GB (1) GB1572125A (en)
GR (1) GR70777B (en)
HU (1) HU178245B (en)
IL (1) IL51768A (en)
IT (1) IT1125767B (en)
NL (1) NL7703250A (en)
OA (1) OA05622A (en)
PL (1) PL103076B1 (en)
PT (1) PT66361B (en)
SU (1) SU645518A3 (en)
ZA (1) ZA771797B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0003517B1 (en) 1978-02-03 1981-03-25 Ciba-Geigy Ag Cyanomethyl ester of 4-(paratrifluormethylphenoxy)-alpha-phenoxypropionic acid; process for its preparation; composition containing this herbicidal compound, and its application
KR840003613A (en) * 1982-02-12 1984-09-15 아르놀트 자일러 에른스트 알테르 Manufacturing method of herbicide
DE3224984A1 (en) * 1982-07-03 1984-01-05 Bayer Ag, 5090 Leverkusen SUBSTITUTED DIPHENYL ETHERS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES
FR2549831A1 (en) * 1983-07-27 1985-02-01 Rhone Poulenc Agrochimie NOVEL ARYLOXYBENZOIC ACID DERIVATIVES AND THEIR USE AS HERBICIDES
US5318946A (en) * 1991-11-27 1994-06-07 American Cyanamid Company 2-(heteroaryloxyphenoxy)alkylsulfonates useful as herbicidal agents

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EG11593A (en) * 1973-07-03 1980-07-31 Bayer Ag Halogenated 4-trifluiromethyl-4-cyano-diphenyl-ethers process for their preparation and their use as herbicides
FR2285859A1 (en) * 1974-09-30 1976-04-23 Lafon Labor PHENYLSULFINYL-AMIDINES AND DERIVATIVES
GB1519147A (en) * 1974-09-30 1978-07-26 Lafon Labor Sulphur and oxygen-containing diaryl compounds

Also Published As

Publication number Publication date
GB1572125A (en) 1980-07-23
BG27722A3 (en) 1979-12-12
AU505610B2 (en) 1979-11-29
HU178245B (en) 1982-04-28
AT354801B (en) 1979-01-25
IL51768A (en) 1981-05-20
JPS52120125A (en) 1977-10-08
IT1125767B (en) 1986-05-14
DD130620A5 (en) 1978-04-19
JPS6146444B2 (en) 1986-10-14
ATA213177A (en) 1979-06-15
ZA771797B (en) 1978-03-29
CH629073A5 (en) 1982-04-15
IL51768A0 (en) 1977-05-31
BE853104A (en) 1977-09-30
FR2346329B1 (en) 1983-11-10
OA05622A (en) 1981-04-30
PT66361A (en) 1977-04-01
NL7703250A (en) 1977-10-04
FR2346329A1 (en) 1977-10-28
AR226410A1 (en) 1982-07-15
AU2376277A (en) 1978-10-05
GR70777B (en) 1983-03-23
PL103076B1 (en) 1979-05-31
CA1095735A (en) 1981-02-17
DE2613697A1 (en) 1977-10-13
BR7702022A (en) 1977-11-08
PL197043A1 (en) 1978-03-13
PT66361B (en) 1978-11-07

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