SU724073A3 - Method of fighting unwanted plant growth - Google Patents

Method of fighting unwanted plant growth Download PDF

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SU724073A3
SU724073A3 SU721820551A SU1820551A SU724073A3 SU 724073 A3 SU724073 A3 SU 724073A3 SU 721820551 A SU721820551 A SU 721820551A SU 1820551 A SU1820551 A SU 1820551A SU 724073 A3 SU724073 A3 SU 724073A3
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carbon atoms
alkyl
alkenyl
hydrogen
group
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SU721820551A
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Russian (ru)
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Вильям Лутц Альберт
Юджин Дайл Роберт
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Американ Цианамид Компани (Фирма)
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
    • C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/58—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1389479 Substituted 2,6-dinitroaniline compounds AMERICAN CYANAMID CO 6 July 1972 [25 Aug 1971] 31784/72 Heading C2C Substituted 2,6-dinitroaniline compounds of the general formula: in which R is 1-ethylbutyl, 1-ethylpropyl, 1- methylpropyl or 1-methylbutyl are prepared by reacting a compound of the general formula: with an amine or the formula RNH 2 . The compounds have herbicidal properties.

Description

Изобретение относитс  к химическим средствам дл  борьбы с нежелательной растительностью в посе вах возделываемых культур. Уже известен способ борьбы с не желательной растительностью, при котором обработку посевов ведут производными 2,6-динитроанилина общей формулы где Ri - алк-йл. С2 , алкенил, алкинил или арил; водород, алкил, алкенил, или алкинил или R и R углеводород с числом атомов углерода 2-6, с которым атом азота образует гетероциклическое кольцо R,- алкил С ; Y - кислород или сера; Z - алкил С.,;- С , галоген или трифтор иетил. Однако известный способ с сорной растительностью малоэффективе бици дов С акти ви  с не при посе -дин где н, если обработку посевов гердом ведут после по влени  всхоцелью усилени  гербицидной вности и избирательности дейстпредлагаетс  способ борьбы желательной растительностью, котором довсходовую обработку вов,, ведут производными 2,6итроанилина общей формулы водород, алкил с числом атомов углерода 1-6, алкеНИЛ или алкилин с числом атомов углерода 2-6; . алкил с числом атомов углерода 2-7, который может быть с пр мой или разветвленной цепью или циклоалкил , алкенил или алкинил с числом атомов углерода 2-6, алкил с числом атомов углерода 1-4, который может быть замещена ггшогеном илиThis invention relates to chemical agents for controlling undesirable vegetation in crops of cultivated crops. A method of combating undesirable vegetation is already known, in which the treatment of crops is carried out with derivatives of 2,6-dinitroaniline of the general formula </ BR> where Ri is alk-yl. C2, alkenyl, alkynyl or aryl; hydrogen, alkyl, alkenyl, or alkynyl or R and R hydrocarbon with 2-6 carbon atoms, with which the nitrogen atom forms a heterocyclic ring R, is alkyl C; Y is oxygen or sulfur; Z is alkyl C.,; - C, halogen or trifluoroethyl. However, the known weedy vegetation method is not very effective in bites with acti vi not at a planting site where, if the gerd is cultivated, the method of controlling the desired vegetation, which is pre-emergent harvesting, is derived , 6-nitroaniline of the general formula: hydrogen, alkyl with 1-6 carbon atoms, alkenyl or alkyline with 2-6 carbon atoms; . alkyl with a carbon number of 2-7, which may be straight or branched chain, or cycloalkyl, alkenyl or alkynyl with a carbon number of 2-6, alkyl with a carbon number of 1-4, which may be replaced with gyrshogen or

алкоксигруппой с числом атомов углерода 1-4} Rj вместе могут образовыватьalkoxygroup with the number of carbon atoms 1-4} Rj together can form

пиперидиновую, пирролидиновую или морфолийовую группу, причем, когда Y и Z означают мети , а водород, или этил, то Rj не может |5ыть этилом;piperidine, pyrrolidine or morpholium group, moreover, when Y and Z mean meth, and hydrogen, or ethyl, then Rj cannot be ethyl;

V - войород, ййкйл с числЬм атрV - voivorod, yykyl with a number of atr

мов-углерода 1-4, алкенил с числом атомов углерода 2-4 , группа СР, -CN или SOjNR R ; . :1-4 moss carbon, 2-4 alkenyl with carbon atoms, CP group, -CN or SOjNR R; . :

Z - алкил с числом углерода 1-4, алКёййЛ с числом углерода 2-4 .или алкил с числом атомов углерода 1-4, который может быть замещен галогеном, алкоксигруппой с числом атомов углерода или 1-.4 или группой NR, и R каждый в отдельнорти означает водород, или алкил с числом атомов углерода 1-4.Z is an alkyl with a carbon number of 1-4, alKoyl with a carbon number of 2-4. Or alkyl with a carbon number of 1-4, which may be substituted by halogen, an alkoxy group with a carbon number or 1-.4 or a group of NR, and R each separately means hydrogen, or alkyl with 1-4 carbon atoms.

Предпочтительным соединением, используемым в данном способе  вл етс  3,4-диметил-2,6-динитро-Н-3-пентиланилин . .The preferred compound used in this process is 3,4-dimethyl-2,6-dinitro-H-3-pentylaniline. .

Пример. Семена сахарной свеклы , хлопчатника, сой, элезины ежовника , импомеи, овсюга, бухарника, высейают в почву, которую обрабатывают испытуемыми соединени ми, указанными в табл.1-12. Спуст  три-четыре недели провод т учет гербицидной активйости в процентах к контролю или в баллах. Шкала оценки: О - нет повреждений; 3 - отдельные п тна ожогов, 5 - отдельные растени  погибки и сильные ожоги, 9 - полное уничтожение растений и задержка роста растений. Тест-растени ; А - . элевзина, Ё - бухарник, В - осот, Г - валериана, Д - бобы, Е - овсюг, Ж - ужовник, 3 - сыть, И - импоме , К - хлопчатник, Л - сахарна  свекла, М - со . Результаты испытаний представлены в табл..1-4.Example. The seeds of sugar beet, cotton, soy, Ezovniki elezeni, impomei, oats, bukharnika, are sown in the soil, which is treated with the test compounds listed in Tables 1-12. After three to four weeks, the herbicidal activity is recorded as a percentage of control or in points. Rating scale: O - no damage; 3 - individual spots of burns, 5 - separate plants of the sinking and severe burns, 9 - complete destruction of plants and delayed growth of plants. Test plants; BUT - . Elevzina, E - Bukharnik, B - Osote, G - Valerian, D - Beans, E - Oats, F - Uzhovnik, 3 - Syt, I - Impome, K - Cotton, L - Sugar beet, M - with. The test results are presented in table.1-4.

Таблица 1Table 1

7 б 7 b

4,4 4.4

СН,CH,

СН, 2г1CH, 2g1

3 . ;СНд,СН СН2СЙ2СЙ СН24,49 О 93 ; SND, CH CH2SY2SY CH24.49 O 9

CffCff

2,2 б 022.2 b 02

Г 1.. . 7- о оG 1 ... 7- o

-о-about

C,HiC, Hi

4,4 4.4

9 8 2,.29 8 2, .2

la,la,

нn

4,4 4.4

9 99 9

2,2iri;2,2iri;

8eight

4,4 4.4

нn

Сд Н„-изо 2,2Sd N „-izo 2,2

I/lI / l

С Нр-трет 4,4 With Nr-ter 4.4

СН, - 2,2CH, 2.2

i S aa S3a- ;:vX-ai S aa S3a-;: vX-a

8 88 8

5 25 2

О ОOh oh

9 89 8

О ОOh oh

ОABOUT

о о оLtd

О 00 About 00

о 000 о 000about 000 about 000

7 О О 7 O O

66

8 3 18 3 1

о о оLtd

ОABOUT

О ОOh oh

О О Oh oh

о оoh oh

0О 0OJ0О 0ОJ

1о1o

99

3 О О3 o o o

оabout

3 О О3 o o o

О О ОLTD

,0, 0

7 б7 b

о о oh oh

о о оLtd

в о оin about oh

9 89 8

оabout

02 О 02 Oh

О ОOh oh

5 five

2 000 2,000

О 3About 3

5five

О 000About 000

б 2b 2

7 5О О7 5О О

оabout

77

Продолжение та6л.1Continuation of ta6l.1

-.,.,;....,.;.„х.,...-.,.,; ....,.;. "X., ...

. o-jr ijiii.si;;-.-; - -.. o-jr ijiii.si ;; -.-; - -.

7 7

. .

СН CH

CHj НCHj N

ОсньMop

СЙз Н CH5CHCH.j,CH2(CH)j 4,4Cys H CH5CHCH.j, CH2 (CH) j 4.4

СН, CjHj ,-нCH, CjHj, n

,,

СН, ° -Н CHjCHjCH (СНт )2 4СН, ° -Н CHjCHjCH (СНт) 2 4

724073724073

Продолжение табл. l,Continued table. l,

о о о о оoh oh oh oh

О ОOh oh

б Оb o

6 26 2

оabout

о оoh oh

о оoh oh

ОABOUT

Продолжение табл.1.The continuation of the table.1.

СН,СН sCH 2,2CH, CH sCH 2.2

Н НH N

Са,Н7-ИЭОSa, H7-IEO

WCRj CHjCH CH2 WCRj CHjCH CH2

СН СНС2Н5СН СНС2Н5

4,44.4

СНСН ,SNSN,

CHjCHC-j HyCHjCHC-j Hy

С Н-у-изоWith N-from

CHj CHj

СИ. CjHSI. Cjh

CiHsCiHs

Н H

Claims (1)

C HjCHCj Формула изобретени  Способ борьбы с нежелательной растительностью, включающий Довсходовую обработку почвы производными 2,6-дйнитроанилина, отличающийс  тем, что, с целью усилени  гербицидной .активности и избира тельности действи , обработку ведут производными 2,б-дини оанилина общей формулы где водород, алкил с числом атомов углерода 1-6, алкенил или алкинил с числом атомов углерода 2-6; алкил с числом атомов углерода 2-7, который может быт с пр мой или разветвленной г.епью, или циклоалхил, алке нил или алкинил с числом ат мов углерода 2-6, алкил с числом атомов углерода 1-4, который может быть замещен галогеном или алкоксигруппой с числом атомов углерода 1-4; вместе могут образовывать пиперидиновую, пирролидиновую или морфолиновую группу, причем, когда X и Y означают метил, а R-f - водород или этил, то R2 - не может быть этиленом; водород, алкил с числом атотом углерода 1-4, алкенил с числом атомов углерода 2-4, группа CF-t-CH или SOjNRjR ; алкил с числом атомов углерода 1-4, алкенил с числом атомов углерода 2-4 или алкил с числом атомов углерода 1-4, который может быть замещен галогеном или алкоксигруппой с числом атомов углерода 1-4 или группой - каждый в отдельности означает водород или алкил с числом атомов углерода 1-4.C HjCHCj Formula of the Invention A method of controlling undesirable vegetation, including pre-emergence tillage with derivatives of 2,6-dinitroaniline, characterized in that, in order to enhance the herbicidal activity and selectivity of action, the treatment is carried out with derivatives of 2, b-dini oaniline of the general formula where hydrogen , alkyl with 1-6 carbon atoms, alkenyl or alkynyl with 2-6 carbon atoms; alkyl with a carbon number of 2-7, which can be straight or branched chain, or cycloalkyl, alkenyl or alkynyl with a carbon number of 2-6, alkyl with 1-4 carbon atoms, which can be substituted halogen or alkoxy with 1-4 carbon atoms; together they can form a piperidine, pyrrolidine or morpholine group, moreover, when X and Y are methyl and R-f is hydrogen or ethyl, then R2 cannot be ethylene; hydrogen, alkyl with 1-4 carbon atoms, alkenyl with 2-4 carbon atoms, CF-t-CH or SOjNRjR group; alkyl with 1-4 carbon atoms, alkenyl with 2-4 carbon atoms or alkyl with 1-4 carbon atoms, which can be substituted with halogen or alkoxy group with 1-4 carbon atoms or a group - individually means hydrogen or alkyl with 1-4 carbon atoms.
SU721820551A 1971-08-25 1972-07-27 Method of fighting unwanted plant growth SU724073A3 (en)

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AR (1) AR194492A1 (en)
AU (1) AU472953B2 (en)
BE (1) BE787939A (en)
BR (1) BR7205530D0 (en)
CA (1) CA988944A (en)
CH (1) CH573704A5 (en)
CS (1) CS180602B2 (en)
DD (1) DD104289A5 (en)
DE (1) DE2241408C2 (en)
DK (1) DK132402C (en)
ES (1) ES406098A1 (en)
FR (1) FR2151415A5 (en)
GB (1) GB1389479A (en)
IL (1) IL39841A (en)
IT (1) IT962214B (en)
KE (1) KE2706A (en)
MY (1) MY7700250A (en)
NL (1) NL177561C (en)
PH (1) PH9657A (en)
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SU (1) SU724073A3 (en)
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Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN145613B (en) * 1975-12-22 1978-11-18 American Cyanamid Co
DE2837499A1 (en) * 1978-08-28 1980-03-20 Bayer Ag METHOD FOR PRODUCING SUBSTITUTED BENZOTRIFLUORIDES AND NEW SUBSTITUTED BENZOTRIFLUORIDES
EP2052612A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
DE102008037629A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
CN109320424B (en) * 2017-07-31 2021-12-21 江苏永安化工有限公司 Method for purifying pendimethalin

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2013510C3 (en) * 1969-04-01 1985-11-14 United States Borax & Chemical Corp., Los Angeles, Calif. Use of 6-trifluoromethyl-2,4-dinitro-1,3-phenylenediamines as herbicides

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ZA724608B (en) 1973-03-28
NL7210935A (en) 1973-02-27
NL177561C (en) 1985-10-16
CA988944A (en) 1976-05-11
JPS4828641A (en) 1973-04-16
TR17956A (en) 1976-07-23
DK132402B (en) 1975-12-01
KR780000132B1 (en) 1978-04-25
NL177561B (en) 1985-05-17
AU4432472A (en) 1974-01-10
ES406098A1 (en) 1976-03-01
DK132402C (en) 1976-05-03
KE2706A (en) 1977-03-04
JPS5842844B2 (en) 1983-09-22
BR7205530D0 (en) 1973-01-16
SE393372B (en) 1977-05-09
DE2241408C2 (en) 1984-01-12
FR2151415A5 (en) 1973-04-13
CS180602B2 (en) 1978-01-31
MY7700250A (en) 1977-12-31
DE2241408A1 (en) 1973-03-01
IL39841A (en) 1975-10-15
GB1389479A (en) 1975-04-03
CH573704A5 (en) 1976-03-31
IT962214B (en) 1973-12-20
PH9657A (en) 1976-01-27
AR194492A1 (en) 1973-07-23
IL39841A0 (en) 1972-09-28
DD104289A5 (en) 1974-03-05
AU472953B2 (en) 1976-06-10
BE787939A (en) 1973-02-26

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