Process for producing heterocyclic phenyl esters (modifications)

专利摘要:
Compounds of formula <IMAGE> (I) wherein R is halogen, CF3, NO2, CN, (C1-C4)alkyl or (C1-C4)-alkoxy, n is zero or 1, X is O, S, NH, or N-(C1-C4)alkyl, Y is O or S, R1 is H or (C1-C4)alkyl and Z is, among others, a cyanalkyl, (subst.) carbalkoxyalkyl, (subst.) carbalkoxyphenyl, sulfoxyalkyl or oxime group, are selective herbicides active especially against weed grasses.
公开号:SU963465A3
申请号:SU802903454
申请日:1980-04-08
公开日:1982-09-30
发明作者:Хандте Райнхард；Маттершток Карл；Бирингер Херманн；Кехер Хельмут
申请人:Хехст Аг (Фирма)；
IPC主号:

专利说明:

(5) METHOD FOR OBTAINING HETEROCYCLIC PENYLES The invention relates to a process for the preparation of new heterocyclic phenyl esters of the general formula RI5 - (j-Y-2. B (4) where R is hydrogen or chlorine in position 5 or 6, or bromine in position, Q NII 6; X is oxygen or sulfur; Y is oxygen or sulfur; Z is a group of the formula —A — COOR where A is a group — or —CH — CH and R /) —C — Cd — alkyl; or Z is a group - CHirCH -CN, -CH-CN or (CH3) I and its variants. Compounds of general formula I possess herbicidal activity and ETHERS and ITS OPTIONS can be found. Cyc ford where, as in agricultural applications, methods for producing heteroic phenyl esters of the total yield Lrvj -fyo-i -Zm and R are a hydrogen or halogen atom, trifluoromethyl, nitro or cyano, alkyl, alkoxyl f, or alkylthio; A is an oxygen or sulfur atom, NH or N-alkyl group; R is a hydrogen atom or an alkyl; Z is carboxylic acid, carboxylic ester, thioether, acyloxymethyl.carbamoylmethyl, of which the compound of the general formula B-f1l Ox) H-AlH / B is HL-Z, and //). Where B is a halogen atom. or tosyl, R and Z have the indicated values in the medium of an organic solvent at a rate of rii boiling the reaction mixture 1J. Compounds of general formula VIII possess herbicidal activity. The purpose of the invention is to obtain nocel pomics of J out heterocyclic phenyl esters, expanding the arsenal of substances with herbicidal activity. This goal is achieved according to the method for preparing a compound of general formula I based on the known reactions of 1.1 J. In the first embodiment of the method, the compound of general formula .1 /; ch.L. where R and X have the indicated values. interact with a compound of the general formula o-CH-c1-t-y / k b where R, Y and Z have the indicated meanings. In the second variant of the method of the compound of the general formula
N
VoHflK) II VO
components by vacuum treatment at a bath temperature of 200s. As a residue, 3 g (8.8% of theory) of methyl ester of (5-chloro-2-benzoxazolyloxy) phenoxy-propionyl glycohydride is obtained; one of the residues O and B is a halogen atom, and the other is a YH group, R RJ. X, Y and Z have the indicated meanings. Example. 2-G methyl ester - {2-benzthiazolyloxy) phenoxy-propionyl lactic acid. , d 2-G2-Genzthiozolyloxy. -. - phenol is boiled with 33.1 g of potassium carbonate and 50.2 g of methyl 2-bromopropionyl-lactic acid in JSO g of acetonitrile for 8 hours. After cooling the salt, filter the acetonitrile off. Residue p After distillation, obtain (82.5 ° from the theory) methyl ester (g-HH-thyroidation) of phenoxy-propionyl-lactic acid with bp. 218-220 ° / P, O mm Hg Example 2, 2-1 Methyl Ester (5-chloro-2-benzoxazolyloxy) phenoxy-x1-propionyl glycolic acid. 25 g of 2 - (- oxyphenoxy) propionyl glycolic acid methyl ester are refluxed for 1 hour with 16.6 g of potassium carbonate 13 1 &amp; 0 ml of acetonitrile until salt forms. After adding 20 g of 2.5 dichlorobenzoxazole, the mixture is continued to boil for 10 hours. At 60 ° C, the salt is filtered off and the acetonitrile is distilled off. The residue is purified from volatile 5-left-acid, which is a brownish, viscous oil; 1.5558. Example 3. Methyl ester of (6-chloro-2-benzothiazolyloxy) phenoc sy propylniloglycolic acid 36.8 g x oranhydride 2-E4- (6-chloro -2-benzthiozolyloxy) | (|) enoxy | propionic acid derived from 35 g of free acid by reacting with 13.1 g of thionyl chloride in 150 ml of toluene for 8 hours at 80 ° C, diluted in 150 ml of toluene, and 12.1 g of triethylamine and 10% are added to the resulting solution at 25–30 ° C. , 6 g of thioglycolic acid methyl ester in 50 ml of toluene. At the end of the addition, the mixture is stirred for 2 hours at 50-6 cPc. Then it is cooled to 25 ° C and washed three times with 150 ml portions of water. The toluene phase is dried over sodium sulfate, filtered and evaporated to dryness. The residue crystallizes after 5 days, and thus, 0.5 g (92.7 from theory) of methyl (6-chloro-2-benzthiazolyloxy) phenoxy propionylthioglycolic acid methyl ester with m.p. 104-106 ° C. i The remaining compounds in the tables are prepared by the methods described in examples 1-3. Herbicidal activity tests. Example 1. Treatment before germination. Grass seeds were sown in pots and the soil surface was sprayed with preparations according to the invention in the form of wettable powders or emulsion concentrates in various doses. After that, the pots were put in a greenhouse for weeks and the result of treatment (as in the following examples) was evaluated according to the following pattern
me
1O - 20 defeats
220 - kQl defeat
3kQ - 6Q% defeat
Thus, these compounds have a high selectivity of action with respect to the weeds in the examples given (Table 1-). H5 C 6Q - 80 damage 5 80–100% damage The preparations according to the invention have a good effect on annuals and partly on perennial weeds. Example .2. Treatment after germination. Seeds were sown in pots and put them in a greenhouse. 3 weeks after sowing, the plants were sprayed with the preparations according to the invention in various doses, on the basis of which wettable powders or emulsion concentrates were prepared, and. after keeping the plants for 4 weeks in the greenhouse, the effect of the preparations was evaluated. The products had a good herbicidal action against a wide range of annual weeds. Some drugs have also been found to be effective against perennial Cunodon dad in Ion, Sorghum, Example 3. Portability in crops. In the remaining experiments in a greenhouse, seeds of a large number of cultivated plants were sown in pots. The pots of the pots were processed immediately after sowing, the rest were left in the greenhouse until 2-3 true leaves were formed in the plants, and only after that they were sprayed with the substances according to the invention. The results, established after -5 weeks after the use of these compounds, showed that the substances according to the invention do not completely or almost completely affect dicotyledonous crops when they are processed before and after germination at a concentration of 2 kg / ha. Moreover, some substances also do not affect cereals, such as barley, sorghum, corn, or rice. Thus, 6512
o-c H-cir- f-bH-dooiij
Table k
SNE About dH3

权利要求:
Claims (3)
[1]
Claim
J. A method for the preparation of heterocyclic ofenyl ethers of the general form - ₂ j
I
[2]
2. A method for producing heterocyclic phenyl esters of general formula I, characterized in that the compound of general formula IV wherein either d-Y-’Z, δ is hydrogen or chloro at position 5 or 6, or nii 6;
X is oxygen or
Υ - oxygen or
Ζ - group of the formula
-A-COOR ^
A - group - CH ^ - or tCH-CH ^ R.-C ^ - C, - alkyl;
Z is a group —CH _X —CH _Z —CN, CH — CN or —N = C (CH <) ,, I cr ₃ characterized in that he is bromine in poseser; sulfur;
where R th X have the indicated meanings, are reacted with a compound of the general formula V w-dH-d-γ-ζ,
I II
Bi о where W is halogen or tosyl;
R., Y and Z have the indicated meanings /
[3]
3. A method for producing heterocyclic phenyl ethers of the general formula D characterized in that the compound of the general formula VI
О Т unity of the general formula 1_Г indicated where R and X are subjected to interaction by the expression of the general formula I I I О-бя-d-Y-z, Л and Z have the indicated meanings, with the compound
BUT γ
reacting with a general formula VII b-z, wherein one of the residues D and B and the other is YH-rpynna,
R, R ₄ , X _y , Υ and Z have the indicated

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引用文献:

---

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

---

---

DE1009421B|1954-09-20|1957-05-29|Boehringer Sohn Ingelheim|Herbicides|

---

GB1041982A|1963-09-30|1966-09-07|Boots Pure Drug Co Ltd|Herbicidal compounds and compositions|

---

DE2223894C3|1972-05-17|1981-07-23|Hoechst Ag, 6000 Frankfurt|Herbicidal agents based on phenoxycarboxylic acid derivatives|

---

DE2623558C2|1976-05-26|1984-12-06|Hoechst Ag, 6230 Frankfurt|2- [4'-Phenoxyphenoxy] propionic acid derivatives, process for their preparation and herbicidal compositions containing them|

---

DE2628384C2|1976-06-24|1984-09-27|Hoechst Ag, 6230 Frankfurt|2- - or 2- propionic acid derivatives, process for their preparation and their use as plant treatment agents|

---

DE2640730C2|1976-09-10|1983-08-25|Hoechst Ag, 6230 Frankfurt|Benzoxazolyloxy and benzothiazolyloxyphenoxy compounds and herbicidal agents containing them|

---

EP0005501B1|1978-05-20|1981-11-25|Bayer Ag|Heteroaryloxy-acetamides, process for their preparation and their use as herbicides|

---

DE2830066A1|1978-07-08|1980-01-17|Hoechst Ag|Benzoxazole, benzothiazole and benzimidazole derivs. - useful as selective herbicides|

---

GR67685B|1979-04-09|1981-09-04|Hoechst Ag|GR67685B|1979-04-09|1981-09-04|Hoechst Ag|

---

DE3115152A1|1981-04-15|1982-12-02|Hoechst Ag, 6000 Frankfurt|"HETEROCYCLIC PHENYL ETHERS AND HERBICIDES CONTAINING THEM"|

---

US4522647A|1982-07-30|1985-06-11|Zoecon Corporation|Substituted phenoxyalkanediones and their herbicidal method of use|

---

DE3236730A1|1982-10-04|1984-04-05|Hoechst Ag, 6230 Frankfurt|METHOD FOR PRODUCING BENZOXAZOLYL AND BENZTHIAZOLYLOXYPHENOXYPROPION ACID DERIVATIVES|

---

JPS6092277A|1983-10-25|1985-05-23|Nippon Tokushu Noyaku Seizo Kk|Substituted phenoxyalkanecarboxylic acid ester, its preparation and herbicide|

---

GB8619236D0|1986-08-06|1986-09-17|Ici Plc|Fungicides|

---

EP0312064B1|1987-10-16|1994-05-04|Kumiai Chemical Industry Co., Ltd.|Thiadiazabicyclononane derivatives and herbicidal compositions|

---

US4954161A|1989-01-09|1990-09-04|American Cyanamid Company|Herbicidal composition and method for safening gramineous crops against heterocyclic phenyl ethers|

---

AU6540490A|1989-10-05|1991-04-28|Hoechst Aktiengesellschaft|Herbicidal, heterocyclically substituted phenoxyalkane carboxylic acid derivatives and process for preparing them|

---

EP0506373B1|1991-03-29|1995-11-29|Tokuyama Corporation|Cyanoketone derivative and herbicide containing it as an active component|

---

JPH06179646A|1992-12-15|1994-06-28|Tokuyama Soda Co Ltd|Cyanoketone derivative|

法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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DE19792914300|DE2914300C2|1979-04-09|1979-04-09|

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