Method of fighting unwanted plant growth

专利摘要:
A herbicidal composition which comprises a carrier and, as active ingredient, a N-aryl triazole of the general formula I:- <CHEM> wherein 2 of X1, X2 and X3 represent a nitrogen atom and the third represents a group C-R2; Z represents a covalent bond, a methylene or imino group, or an oxygen or sulphur atom; R1 represents an optionally substituted alkyl, aralkyl, alkenyl, cycloalkyl, cycloalkenyl, heteroaryl or aryl group; R2 represents a hydrogen or halogen atom or an optionally substituted aryl or alkyl group; and Ar represents an optionally substituted aryl group; the use of such triazoles as herbicides; certain novel triazoles within formula I and their preparation.
公开号:SU1498375A3
申请号:SU853981451
申请日:1985-11-18
公开日:1989-07-30
发明作者:Мансур Мансури Музаммил；Макартур Аласдэйр
申请人:Шелл Интернэшнл Рисерч Маатсхаппий Б.В.(Фирма)；
IPC主号:

专利说明:

This invention relates to chemical methods for controlling weed and undesirable ragte. (- Tew.
The purpose of the invention is to increase the herbicidal effect of the method based on the use of triazole derivatives.
Below, the pre / 1 steps of the proposed 1 ba, the method of their preparation and the hi-mers, i.-1ln) with 1, test the effectiveness of this method.
II p. m e |) 1. Preparation of 1- (3- griffluoromethylphenyl) -5-phen (5 x -1, 2,4-triuyla.
To paci Bojjy O, /) g (JitHojia in dry dimeti. Ph. Rmamids iri sk) 1 g rpt - Miiai, 1 K.-i.iHH and iivb-le rastornor base added t) solution of 2.3 g 1 - (3-trifluoromethylphenyl) -5-bromo-1, 2, 4-triazole in 1 O OI of dry diethylformamide. The reaction mixture is stirred for 2 hours at 70-80 ° C, cooled, poured into ice-water mixture, the solid product is filtered off, washed and dried. Get the target substance with so pl. 43-45 S.
Under the conditions of Example 1, other compounds are prepared, a list of which is given in Table 1.
four
WITH
kx) with
SP
 CM
Definition of coat of arms Example 2, JUVlHoro action.
Held oribiThi nkijfiu ho and nocijfiu ho. processed Active HcriueciBa (general) formulas
X, Xg
{I | 1 R, H k, / N
Compounds 7, 13-17 were isolated as oils and characterized by mass spectra (see Table 2).
Table 2
Mass spectrometry data of compounds
Table 3 Herbicidal activity of the compounds
The continuation of the table.3 Herbinidna activity of compounds

权利要求:
Claims (1)
[1]
Formula and Test 25
A method of combating undesirable vegetation by treating it with a triazole derivative, with the exception that, in order to increase the herbicidal effect, a compound of the general formula is used as a triazole derivative where X and X £ ~ are not the same and mean —N— or —SI—;
Y is hydrogen or trifluoromethyl;
Z is oxygen or NH;
- phenyl, m-fluorophenyl, p-fluorophenyl, m-chlorfe nyl, m-bromophenyl, m-methylpheyl, m-trifluoromethylphenyl, m-methoxyphenyl, m-cyaanophenyl, cyclohexyl, 3-methylcyclohexyl, pyridin-3-yl, provided that when X 2 is N-, Z is oxygen, Y is trifluoromethyl, Ry-phenyl, mfluorophenyl or bromfe hhjIjY is hydrogen when X <- -Μ-, X 2 -CH^-, Ζ is oxygen and R_tphenyl; when Ζ NH, X₍ - -Ν-, X₇-SI-, Υ - trifluoromethyl and I, phenyl n, in an amount of 1-5 kg / ha.
Table 1
Active substances of the general formula
CompoundX 2 - ^R -i Z Y T. ill. ° C I 2 3 4 5 6 7 - - ____ 1 N SI Phenyl 0 T riftermethyl 43-45 2 N SI Phenyl 0 Hydrogen 48-50 3 N SI m-fluorophenyl 0 Trifluoromethyl 53-54 4 N SI p-fluorophenyl 0 Trifluoromethyl 59-60 5 N SI m-chlorophenyl 0 Trifluoromethyl 70-72 6 N CH m-methylphenyl 0 Trifluoromethyl 48-52 7 N SI Cyclohexyl 0 Trifluoromethyl - 8 N CH m-trifluoromethyl-Trifluoromethyl 58-59 phenyl 09 N CH m-cyanophenyl 0 Trifluoromethyl 105-106 10 N CH m-methoxyphenyl 0 Trifluoromethyl 4 5-47
Continuation of tab. ~, 1 1 1 ¹ 1³ 1⁴ . .L 5 1. b 1 Ϊ eleven N SI Pyridin-z-yl 0Trifluoromethyl '--53 12 N SI Phenyl NHTrifluoromethyl 67-72 thirteen N SI Phenyl NHTrifluoromethyl - (HC1) 14 TO SI 3-methyldicloghex- 0Trifluoromethyl forces fifteen SI N Fenia 0Trifluoromethyl - 16 Wed; N m-fluorophenyl 0Trifluoromethyl - 17 SI N m-bromophenyl 0Trifluoromethyl - Connections 7, 13 - 17 are highlighted as oils and characterized by mass spectra (cm . table 2) . T a b l and 2 Mass spectrometric data compounds
Connectednation Characteristic Molecular mass 7 312 (M * + 1) 311 thirteen 305 (M ⁺ + 1) 304 14 325 (M ⁺ )325 fifteen 306 (M ⁺ + I) 305 16 324 (M ^f + 1) 323 17 384 (M *)384
Table 3
Herbicidal activity of compounds
Connection
Dose, g / I a Subsequent processing (activity in points) Pre-emergence processing (activity in points) Experienced plants * Experienced plants * To | P | E | 0 | nj J'jc.C J C to | P | E] 0 | L | G j SS [S
5 5 6 7 7 7 8 9 1 12 5 5 6 8 8 5 5 4 5 6 8 8 6 2 1 4 2 3 2 3 5 4 3 5 5 5 7 7 8 9 8 1 3 2 4 5 7 8 5 5 5 4 7 7 8 8 8 ά 1 2 1 4 5 7 8 5 5 5 5 7 7 8 9 7 5 1 2 3 6 6 8 8 6 S 4 4 7 7 8 8 8
8 6 4 9 7 5 8 9 4 7 4 2 9 5 1 5 8 0 5 1 0 4 2 2 3 3 0 4 0 0 2 1 0 1 2 0 5 5 4 9 8 6 9 8 4 3 3 2 9 5 5 5 2 1 4 h 3 9 7 5 6 8 2 4 1 1 7 2 2 3 ) 0 4 3 4 8 6 4 7 6 I 4 2 3 7 4 2 2 2 0 4 0 3 9 5 2 3 3 1
Continuation of Table 3
Herbicidal activity of compounds
Connection. Dose kg / ha Post-emergence treatment (activity in points) Pre-emergence processing(activity in points) Experienced plants * Experienced plants * To | P | E j 0 | l | Gj SS | FROM K j P * | E | · 0 | L] r | ss | FROM
⁶ 1 3 2 4 5 7 8 5 4 0 14 3 0 10 0 5 7 4 7 6 7 5 5 6 5 4 8 5 3 4 6 4 7 1 5 2 5 4 7 4 4 4 - 2 5 2 - - - - 5 5 3 8 5 7 7 7 6 4 4 9 7 5 7 5 - 8 1 3 2 6 3 6 6 6 6 3 2 8 5 2 6 3 - 5 6 - 6 3 7 7 4 7 4 • 3 1 6 6 8 5. 2 9 1 4 - 4 2 6 7 - 6 2 2 7 4 4 7 5 - 5 8 5 8 5 7 8 8 8 4 5 7 7 4 6 6 2 10 1 5 4 7 3 5 6 7 7 2 4 - 5 2 6 5 1 5 4 fifteen 4 7 6 7 7 2 0 4 4 5 4 7 - eleven 1 2 - 2 2 5 5 6 6 - - 4 2 5 4 5 - 5 4 2 7 3 6 6 6 5 3 3 8 4 4 8 8 4 12 1 4 16 2 5 4 6 5 0 0 4 1 4 4 2 1 5 2 2 6 2 5 6 5 5 0 2 8 3 5 8 7 2 thirteen 1 2 2 6 1 4 5 4 5 0 0 3 0 2 6 3 0 5 5 A b 5 6 6 7 6 4 4 8 6 5. 6 3 0 14 1 3 2 4 3 5 5 . 53 2 7 2 0 5 0 0 5 7 4 8 6 7 7 8 6 6 6 9 7 8 8 9 3 fifteen 1 5 3 6 4 6 6 7 6 4 4 9 5 6 4 7 1 16 5 6 3 8 6 7 7 9 8 4 3 9 7 7 8 9 3 1 3 fifteena 3 6 6 8 8 1 0 7 5 3 6 5 0 17 5 4 0 5 5 5 8 6 5 0 0 6 4 3 7 6 0 1 2 0 2 3 4 7 5 4 0 0 2 0 0 3 6 0 5 5 14 2 4 4 6 2 2 0 8 2 4 . 2 5 2 A 1 0 0 0 0 3 3 2 0 0 0 7 0 0 0 0 0 * to - Corn »R - rice , E - blackberry ABOUT - wild oats, L - linen, , G
mustard, OS - sugar · beets, C - soy.

类似技术:

---

公开号 | 公开日 | 专利标题

---

US4427696A|1984-01-24|Fungicidal acyl anilides

---

US5367093A|1994-11-22|Insecticidal phenylhydrazine derivatives

---

US5438123A|1995-08-01|Insecticidal phenylhydrazine derivatives

---

SU1498375A3|1989-07-30|Method of fighting unwanted plant growth

---

IL46988A|1977-12-30|N-|-n-furan-2-ylcarbonyl aniline derivatives their manufacture and microbicidal and fungicidal compositions containing them

---

US4098895A|1978-07-04|Triazolylacetanilide compounds and microbicidal compositions

---

US4143155A|1979-03-06|Sulfonylglycolic anilide fungicides

---

US4094990A|1978-06-13|Certain phytofungicidal n-furanyl carbonyl and tetrahydrofuranyl carbonyl, n-|phenyl alanines

---

US4160839A|1979-07-10|Carbamyltriazole insecticides

---

US4397678A|1983-08-09|Plant growth regulators

---

US4075349A|1978-02-21|Microbicidal compositions

---

CA1206160A|1986-06-17|Microbicidal compositions

---

US3999974A|1976-12-28|Barbituric acid derivatives

---

EA000109B1|1998-08-27|Triazine derivatives

---

US4399143A|1983-08-16|Phenoxybutyltriazole compound, agricultural and horticultural fungicidal composition containing the same, and process for producing the same

---

US3955957A|1976-05-11|Phosphoryl-acylamines for inhibiting plant growth

---

CA1071221A|1980-02-05|Microbicidal compositions

---

DK165689B|1993-01-04|1,5-DISUBSTITUTED IMIDAZOLD DERIVATIVES, PROCEDURE FOR THE PREPARATION OF SUCH COMPOUNDS, FUNGICID PREPARATION CONTAINING SUCH COMPOUNDS, AND USE OF SUCH COMPOUNDS AS FUNGICIDES

---

US4220790A|1980-09-02|1-N,N-Dimethylcarbamyl-3-tert.butyl-5-methylthio-1,2,4-triazole

---

SU1264830A3|1986-10-15|Fungicide agent

---

IE47988B1|1984-08-22|Novel 2,6-dinotrobenzenamines,their preparation composition containing them and their use as fungicides

---

US4153712A|1979-05-08|Pyrazolylacetanilide compounds and fungicidal compositions

---

SU727103A3|1980-04-05|Herbicidic and fungicidic agent

---

US4214005A|1980-07-22|Fungicidal alkoxyalkoxyacetyl acylalanines

---

US5543404A|1996-08-06|Pesticidal phenylhydrazinephosphates

同族专利:

---

公开号 | 公开日

---

CS252836B2|1987-10-15|

---

OA08136A|1987-03-31|

---

FI854531A0|1985-11-18|

---

EG17719A|1991-03-30|

---

DK532685D0|1985-11-18|

---

EP0185401B1|1990-06-06|

---

PT81511A|1985-12-01|

---

FI854531A|1986-05-21|

---

GR852778B|1986-03-18|

---

EP0185401A1|1986-06-25|

---

PT81511B|1987-11-11|

---

AR241470A1|1992-07-31|

---

HU199242B|1990-02-28|

---

AU5000285A|1986-05-29|

---

CS831685A2|1987-01-15|

---

NZ214219A|1989-08-29|

---

ZW20485A1|1986-02-26|

---

PH21184A|1987-08-12|

---

CN85108495A|1986-07-30|

---

DK532685A|1986-05-21|

---

KR860004035A|1986-06-16|

---

JPS61129172A|1986-06-17|

---

MA20576A1|1986-07-01|

---

GB8429307D0|1984-12-27|

---

HUT41224A|1987-04-28|

---

ZA858816B|1986-07-30|

---

AU598449B2|1990-06-28|

---

AT53277T|1990-06-15|

---

DE3578032D1|1990-07-12|

---

BR8505777A|1986-08-12|

引用文献:

---

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

---

---

DE818048C|1949-08-31|1951-10-22|Basf Ag|Process for the preparation of 1, 2, 3-triazole derivatives|

---

US3470196A|1965-11-12|1969-09-30|Monsanto Co|Preparation of v-triazoles|

---

US3489761A|1967-03-06|1970-01-13|Du Pont|Certain n-triazoles|

---

GB1288540A|1968-09-04|1972-09-13|

---

CA952269A|1971-06-21|1974-08-06|Schlegel Manufacturing Company |Strap handle|

---

IT1009941B|1974-04-19|1976-12-20|Sir Soc Italiana Resine Spa|HERBICIDE COMPOUND|

---

JPS5649371A|1979-09-28|1981-05-02|Nippon Nohyaku Co Ltd|Preparation of 1,2,4-triazole derivative|

---

JPS56139469A|1980-03-04|1981-10-30|Sandoz Ag|Improvement on organic compounds|

---

GB2070607A|1980-03-04|1981-09-09|Sandoz Ltd|1--5- phenyl-1,2,3-triazole derivatives useful as plant growth regulating agents|

---

FR2570699B1|1984-09-24|1987-08-28|Roussel Uclaf|NOVEL PROCESS FOR THE PREPARATION OF 4H-1,2,4-TRIAZOLE DERIVATIVES, NOVEL TRIAZOLES THUS OBTAINED, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM|DK277086A|1985-07-12|1987-01-13|Hoffmann La Roche|triazole|

---

KR100290617B1|1993-08-10|2001-11-26|나가야마 오사무|How to prepare sulfide compound|

---

DE19525973A1|1995-07-17|1997-01-23|Bayer Ag|Sulfonylaminocarbonyltriazolinone with heterocyclyloxy substituents|

---

TW533205B|1996-06-25|2003-05-21|Novartis Ag|Substituted 3,5-diphenyl-l,2,4-triazoles and their pharmaceutical composition|

---

DE19816882A1|1998-04-17|1999-10-21|Boehringer Ingelheim Pharma|Use of known and new triazolone derivatives as medicaments, especially for treatment of neurodegenerative disorders and cerebral ischemia|

---

DE602004025258D1|2003-08-06|2010-03-11|Vertex Pharma|AMINOTRIAZOL COMPOUNDS AS PROTEIN KINASE INHIBITORS|

---

EP1921072A1|2006-11-10|2008-05-14|Laboratorios del Dr. Esteve S.A.|1,2,3-Triazole derivatives as cannabinoid-receptor modulators|

---

EP2264008A1|2009-06-18|2010-12-22|Bayer CropScience AG|Substituted enaminocarbonyl compounds|

---

TW201418242A|2012-10-26|2014-05-16|Du Pont|Substituted triazoles as herbicides|

法律状态:

优先权:

---

申请号 | 申请日 | 专利标题

---

GB848429307A|GB8429307D0|1984-11-20|1984-11-20|Heterocyclic herbicides|

---